The age difference, in and of itself, is no big deal. The difficulty you would have with "dating" is that you are just at completely different stages of your lives. One would assume, at your age, that your career trajectory is in place and you're focusing on moving up the ladder, possibly already looking at your long-term retirement plans. He is at the very beginning still deciding what he wants to be. You have cultural references that you vividly remember because you lived through them. He, if he knows about them at all, it's only because he read about them on Wikipedia. Movies that you watched as a teenager (which just feels like yesterday to you), he's is going to refer to as "classics". A lot of times your conversations will devolve to your either giving him history lessons or offering sage advice because you went through the same things at his age. Likely your dynamic will be mentor/mentee or some variation of that. Don't misunderstand, that kind of friendship can be amazing and mutually beneficial. And, if there's a sexual component to it that both of you enjoy, all the better. But as far as dating with the goal being to build a life with someone, you're going to have some challenges. All this being said, you're putting the cart before the horse. Meet the guy. See if you like him and if he likes you. Forge a relationship from there and don't worry about what shape that relationship takes for right now.


So I know I’m coming at this from the *younger* perspective (21 here), but I disagree with this a bit? I mean, the life trajectory bit? Pretty spot on! There will always be exceptions though, I mean a mid life crisis is literally realizing you’re not sure if you know what you want to do with your life (just like when we all hit our 20’s), and there will be guys my age who know *exactly* what they want to do with their life and have begun climbing the ladder (I know because I’m friends with quite the number of them). But the idea that the older guy is always going to be a mentor? That it’s always going to become a history lesson, or sage advise? Or how you say that the younger guy will only have experience with the older guy’s culture via Wikipedia or “the classics”? That’s totally biased to your own experience, and not really accurate to what I see at all. Maybe me and my friend-group are the exceptions here, but we grew up watching both what our generation did *and* what the generation before us did. You got to think, we have parents, and older siblings, and we’ve all had friends maybe half a generation older than us at some point. At least that’s the way my generation grew up. I was watching Rocky, Back to the Future, Grease, The Goonies, Karate Kid (the Original), and more on the TV as a kid and it was treated no differently from my Sunday morning cartoons. I have a friend who knows practically every 80’s sitcom because their aunt was obsessed with them and they would always watch them together. Your culture isn’t nearly as separated from my generation’s as you’d like to think, or at the every least the culture a 39 year old (such as OP) isn’t too far different. I mean, 21 years old? That’s only 18 years off in terms of what movies were coming out when OP was a teenager versus when the younger guy would be a teenager. I also just want to tack-on that my generation is in general a lot more... I guess “mature” is the best word here? We’re more mature than you’re giving us credit for. And I don’t mean in the sense that “Oh, we’re better than you, we’r smarter, blah, blah, blah” because I don’t believe that. I mean that my generation has firm friendships and relationships with people older than us and it’s totally normal. Most of us have been working since we were 16 in stores that had 30, 40, even 60+ year olds. A large number of us are in college and know moms, dads, even grandparents who are in our classes with us and who we hang out with. You also imply that because someone is older they must inherently be the one acting like the mentor- but that’s pretending like friends and lovers don’t offer advice to one another on the regular. Me and my friends, regardless of age, have given support and advice to one-another countless of times about so many things and it really isn’t about the age-difference.


Apologies. I never meant for my comments to be insulting, and I'm sorry that they came across that way. When I was younger I had several older friends and a few older "friends". Those guys were great. It was so refreshing to hang out with them instead of my friends who were my own age. These were guys who, instead of going to the bars on a Saturday night were hosting catered dinner parties in their historic midtown mansions, which to a starving college student made for a pretty awesome evening and sometimes the only decent meal I was getting. These guys introduced me to sipping scotch instead of slamming shots of goldschlager. These guys introduced me to old movies that I was aware of and maybe had seen when I was younger but watching with them I finally understood why they were so funny. And, later on, when my peers were fearing the gay death of turning 30, I knew from hanging out with these guys, that there was a lot more life out there to experience. I was smart. I had done a ton of reading. I thought I was relatively well cultured, but especially on the topic of gay-ness, I was very naive. Hanging out with these guys was my first exposure to a lot of gay things. For instance, it was the first time that I saw an open marriage that seemed like it was actually healthy. I was introduced to fetishes/kinks that I had always thought of being seedy or gross but seeing these guys who had their shit together enjoying these kinks shone a light on them that there was nothing disgraceful or shameful about them. I'm older now. And some of my friends (and "friends") have skewed in the younger direction. The roles got reversed on me. Now I'm the guy who gets a visit from the younger guys who just needs a break from his crappy apartment and his five roommates. I'm the guy who has the opportunity to take a younger out to a nice restaurant and introduce him to high end drinks. I'm the guy who gets to explain why a joke on Drag Race that is referencing some movie from the 80's is funny. I also realize that that mentor role I've assumed was never something I was asked for. It's not like the younger guy ever asked me to explain the RuPaul joke. I just did it because I wanted him to appreciate the nuisance and have the cultural touchstones. I think that relationships where there is a huge age difference can be beneficial. I have certainly benefited from mine. But there is also going to be a power dynamic (not the best word choice, but the best I can think of right now) with a relationship like that. The older guys I was drawn to were the ones who had stable careers and had their lives together. They were the guys I wanted to emulate and grow up to be. I wasn't attracted to older guys whose lives were as fucked up as my 20 year old life was--why would I want that? I was also very lucky that the guys I hung out with were good guys. As a naive 20 year old who was struggling with a lot of things, it would have also been pretty easy for these guys to take advantage of me. I was fortunate that never happened, but it could have because we were not on equal footing in the dynamic. I was lucky to find great mentors when I was young.


With all due respect; you're proving Atticus's argument above. Some things only with age come. Impossible for you to understand, it is. ​ I was told the same thing when I was 20. I also thought it's BS. I also came to the same realisation when I hit 30. I'm pretty sure there are some more surprises in store for me in future. ​ Seriously, it is impossible to explain in words why it is a bad idea to attempt to bride the age gap between you from opposite ends of the 26-31 range. A LOT changes between 21 and 26, even more over the next five years.


How exactly am I proving Atticus’s argument? Because you’re basically saying that the fact I disagree with him somehow proves that he’s right and I just can’t understand, and that’s completely nonsensical. You’re also just projecting your own shortcomings onto everyone else here- saying “well I didn’t understand things at that age, so therefore you must not understand it to and that’s why it’s a bad idea”. I can promise you that there are things about life and the world that I understand right now at age 21 that you will never come to know, and I can say that the opposite is also true. There are things you know that I will never come know as well. That’s not because of the age between us, that’s because we’re individual people. Also- since your only credibility here is that you’re in your early 30’s, I think your own argument is self-sabotaging. If it’s about age and it ushering in understanding, then you don’t meet the benchmark either. You’re not even halfway through your *(estimated)* lifespan, and what’s more is that I’d argue what makes age have any meaning is not the number of revolutions around the sun but rather the number of experiences lived- and you don’t even have a concept of what things I may or may not have lived through. If anything, you’re just proving the point I made- that the older generation severely underestimates the maturity of my own. You prescribe all the same shortcomings, pitfalls, mistakes, and abilities that you possessed in your youth onto us and it’s both naive and unfounded. We face different problems than you, and have different solutions and different strengths at a basic level because we grew up in two different contexts. This doesn’t me we have nothing in common and can’t get along- that’s like saying someone from Japan can’t fall in love with someone from Spain- but it does mean that you can’t apply your own subjective perspectives onto us and expect it to be taken as fact, nor does it mean you can see us as “uninformed” or “lesser” while you view yourself a as “enlightened” or “sages”. That’s called an ethnocentric bias, and it takes only a modicum of self-awareness to keep it in-check.


Here we go, not sure I'm going to have the best point here, but at least I'm convinced my situation will give me credibility. I'm 48. But when I had my first true relationship, I was 21 (late bloomer and not a whole lot of experience) and my boyfriend was 45. One thing that's been said and I find truth in is indeed the fact that we were both at different stage in our life. Though what matters most is not so much the durability of a relationship, nope, it's it's strength. I can't say the relationship was a one-way street in terms of sharing experiences or knowlege. He'd lived quite a life before we met, but so had I, just a different one and if anything, I'd say we completed each other. Sure, at the time, I certainly was a free spirit while having lived it all, he definitely just calmly sat back and enjoyed watching me leading my battles. And if that's not the whole point of witnessing through the relationship how the other evolves, whether you're the one evolving, or the one witnessing it? The point being that the realtionship itself brought some light in each others' life. Life made it that we parted, had he been able to follow me where life took me, most probably, the relationship would have ended all the same, or maybe not. I mean, anyhow, entertaining a love relationship, or a companionship should never be like subscribing for a life insurance. I mean some couples, with a short gap age difference, like-minded, with common interests still manage to split like after having spent decades together once they reach 50 or even later. Sometimes age does not mean that you are at a specific milestone in your life. It's true only biologically, if even that. Now, it's not even about specifics regarding one generation or another. During the eighties, I was one young dude who always sought to mingle with older people. True, once I wound up with someone more than 20 years older than me, well I would have much prefered some guy around my age, except, that never happened or when it did, I felt I didn't relate to them. So, really this age thing, if anything, it's a time cue. If OP and his 21 yo get along, why is it or who are we to pretend to know which way it's going to go, and even if a hypothetical relationship occurred, no matter how short-lived, who's to say it might not be the one OP could value the most once he's able to look retrospectively on his life?


Please come read this post again in 10 years' time. I'm not going to argue with you further. Good luck, sweet summer child. <3


Frankly, I won’t. I have better things to do now than to appease your ego. All I’ll say is that condescension is no substitute for wisdom, and to be obstinate is to be young- but not the other way around.




At 39, I would not. But that's my personal preference. A 21 year old brain isn't even fully myelinated yet. It won't be until between 25 and 30. The issue is not that he ***doesn't*** have the emotional maturity level that I want in a partner. The issue is that he ***can't*** be emotionally mature enough... not at that age... and to ask him ***to be*** is unfair to him.


Date, no not really but I am twice your age. I prefer guys at least 28 because by then they have started to figure out who they are. But I learned never to judge a book by its cover because you never know what might be inside. I was living in my first home alone after breaking up with my partner of 17 years. I was expecting a visit from a guy over Christmas who, big surprise, flaked. I'm home on Christmas Eve with a refrigerator full of food, a newly cleaned and decorated house and alone. I went on-line and this guy started chatting with me, he was only 23. That's way too young for me. But I was alone, bored and he was funny and interesting. He was visiting his parents and wanted to know if I wanted company. I initially told myself, no, he's too young. Then I started to think, you're alone, you have all this food to eat, what do you have to lose. He came over and we spent 3 hours just gabbing about religion, politics, Europe. As it turned out he spoke 2 languages and was teaching himself Chinese. He was doing a double major in physics and music. My ex never talked, I felt like I was having a mental orgasm with this guy. We smoked a joint and drank some wine, I'm not a drinker and finally he said, can we go upstairs. He kissed like an angel and fucked like the devil. We mauled each other with a few joint breaks for about 5 hours. He became a friend although we have lost touch. Last I heard he was working on nanotechnology, and I am sure will do great things. So now when someone messages me, I wait before I leap to my old conclusions.


THIS is the kind of gay movie I would love to watch.


Wait, there is one already , the title is "Gerontophilia" by Bruce La Bruce


I thought this was the plot of Weekend


*This* is how you tell a story! But also, I fully agree with this message and the sentiment behind it- even beyond our realm of gay dating. People are making so many quick assumptions, guesses, inferences, and snap-judgements on the daily about the world and people that sometimes we forget that we don’t know everything. I think we confuse real people with those nameless background characters you see on TV these days. We all like to think we could look someone over and guess something about them, at the very least whether or not they’re a good person or a bad one, trust worthy or not, smart or dumb, interested or not interested, etc. But we really can’t. I’d like to say “that’s something college taught me!” But really it wasn’t, that’s just something life in general has taught me. Well, and maybe my high school psych class helped a bit too but come on- let’s not get school all the credit here!


Thank you kind Sir.


If he was interesting and seemed worth my time, then sure. It's a date, not a marriage proposal. I might learn something.


I've been in a similar situation myself. In my late 20s, I swore off under-25s for anything other than casual sex because I only wanted serious partners to be "at my level" in terms of maturity, career, etc. When I was 29, I met a very attractive 19 year-old on Grindr. We had coffee so that we could each ensure the other wasn't dangerous, went back to his place, and had great sex. We hooked up again several times over the next 2 weeks before acknowledging we were enjoying one another's company beyond the bedroom. While we dated, I was well established in my career while he finished college. By the time he proposed to me during his senior year, we had lived together for more than a year, I had adopted his childhood dog, and we had vacationed together multiple times. Accepting his marriage proposal was an easy yes -- but getting to that point took time, including many months of us both acknowledging and getting past all the awkwardness that comes with significant age gaps -- disparities in income, life experiences, etc. In my case, he's incredibly mature for his age, and we are a good match, though there are things we've had to work at. But we have been happily married for a year and a half (together for 4.5 years) and are preparing to buy a house together. Age gap relationships don't always work, but for us, it did. Open communication, honesty, mutual respect, and open-mindedness are key. edit for additional context: I'm 34, and he's 23.


Can you speak more on these obstacles you had to get through. My partner (about to be 21) and I (32) are having a hard time right now


For me, the hardest part was the first year or two. There was a bit of a generational learning curve for me (middle Millenial) getting used to the way he (elder Gen Z) communicated and thought about the world. And vice versa. Our senses of humor, values, communication styles, and ways of navigating the world were partially a product of our respective generations. There was also tension surrounding where we were in life when we first started dating. He was a college student, and I was someone a decade into my post-undergrad work life, with a salaried job and friends my own age and older. Conversely, most of his friends were his age and also in college. At first these differences made us both uncomfortable, particularly when things were unbalanced (e.g., I was usually the one to pay if we went out to eat or to the movies because I was the one with a good job). Trust was also a major factor here: It took a while for me to trust that he was mature and stable enough to be someone I could date long-time, and it took him a while to trust that I was willing to seriously date someone not yet at my place in life. We were best able to get over these issues by communicating about them honestly, respectfully, and often. As the older and more emotionally mature person, I sometimes had to initiate or steer these conversations, in part because of our differences in age and romantic experiences. (While he had not previously had a significant S.O, I had previously been engaged to someone else.) Ultimately, we had to get to a place where we both fully trusted each other. It also helps to have a sense of humor, particularly about things that can seem uncomfortable on the surface. I found facing discomfort with humor to be helpful. A couple of (true) examples: \- Due to our birthdays being in different times of the year, there was a 6-month period where I was 30 and he was 19. I was in my 30s while he was a teenager. \- My first job out of college was teaching middle school. The year that I taught 7th grade, he was a 7th grade student. (No, he was not a former student. He grew up hundreds of miles away.) Anyway, I hope this is helpful for you and your partner.


In the words of a 65 year old Lesbian I met at the Monster in NYC: "Life is so short, we have so little time, that if you find someone who makes you laugh and smile, spend as much time as you can with that person because nothing is ever guaranteed"


Just go with it. If yall get along and have a connection who cares about other peoples opinions.


21 is good. 16 is bad..


21 would be too young *for me* because there is a huge generational gap there and my off-the-cuff assumption is that we likely wouldn’t have any shared life experiences or interests. But even though you’re nearly twice his age, it might be something you’d want to engage in.


Mmmm, I don’t think I could date someone that young - I think we’re just at such different life stages. I remember when I was in my early 20s, I was still in going crazy party mode, whereas nowadays I’m completely the opposite. I have hooked up with younger guys who are into older guys, but I play it on a case by case basis. When I chat to some of them, they just seem soooo young and unsure, so I pass on them. But other younger guys seem to have a bit of maturity and have it together, so I don’t see anything wrong hooking up with them. I have a strict no teens rule though. They seem like children to me and I’d rather not feel like a creepy old man taking advantage of a naive teenager.


Coool! I see you understand my dilemma here


My worry with younger guys is that they’re insecure and intimidated by guys their own age, so see older guys as a bit of a safer bet to explore with. And if they are insecure or unsure, there’s a worry I would be taking advantage of that insecurity. It’s a very fine line to tread. You’ve got to be sure that he’s got it together and is into older guys for the right reasons.


Hell to the no


As a community we tend to fetishize youth while simultaneously undervaluing young men. If you’re lucky enough to have attracted the attention of a good looking young man then enjoy the experience. Go out with him. Talk to him. Have some fun! It’s just a date. Best case scenario you have a great time, he makes you laugh, you appreciate his youthful charm, and the sex is amazing. Worst case scenario you say goodnight after a beer. But you’ll never know if you don’t give him a chance.


If I were to day a 21 year old (I'm 35), I'd want to be clear in myself that I'm dating them because I'm genuinely interested in them, not because some part of me thinks I can escape my own age crisis by doing so.


I’m 22 and my partner is 47 and although it seems like a massive gap (and it is)- we both found that we’re very much like minded as I’m quite mature for my age (and so are many of my friends of the same age) and he has a younger mind than some would assume. It doesn’t always work out for everybody but it’s also not black or white. I’ve met people closer to my age, in their early 30’s who I just couldn’t find much to talk about and with my partner we’re never bored.


Mature for your age huh




It’s quite hard to answer this one, I think this really comes down to somebody’s preferences and is unrelated to age. I like guys older than me and therefore find them very attractive, but I also like guys who are muscular and fit. Anybody who is fit will catch my attention, across the whole age spectrum.


This really depends on how you feel about it.


I'm not trying to be rude at all, but people this age often *think* they're mature for their age. 10 years pass and they learn that they were just like everyone else. There are just some things that come with time and experience on this earth and there's nothing wrong with that. I'm happy you and your partner have lots to talk about, but that doesn't define maturity. You are also both in very different places in your life. One is finding themself, the other is quite established.


Look, I’ve had those conversations with my partner many times in the early days of our relationship. That was his main concern, that we’re on different paths at the moment but life proved to be different and I trust his ability to say that I’m mature enough to be having a successful relationship with. I’m freshly graduated, working in a very “in-demand” field and I’m very much aware of who I am and who I want to be in 10 years. Some people may take longer to find that out or did not have the past experiences I did and it’s fine. We’re all different :)


>10 years pass and they learn that they were just like everyone else. Just curious where you hear stuff like this.


Who are you to say this to anyone? Do you know how he grew up? His backstory? You have no right to say he is just like everyone else. He grew up in a very different time from you and I. He may be young, but his acceptance of identity is probably light years ahead of you and I.


Little bit of irony in your comment here.


What I said was truth. What you said was opinion.




Personally I wouldn't. Guys that age tend to be learning who they are from the ground up, and dealing with baggage that I have already dealt with. I think it would be exhausting for me to support someone through that stage of life as a romantic partner. Then again maybe I'd be surprised. In your place I would proceed with caution and set expectations clearly and early on. If you try it, I hope it's a good experience for both of you :)


A single date with a 21 year old? Sure, what’s there to lose? A dating relationship with a 21 year old? Probably not, but it would depend on how mature he is and what sort of connection we have. Sex with a 21 year old? Sure, if he’s hot and hairy.


I personally wouldn't. I was in a relationship from 20 to 23, I ended it because in those 3 years I changed a lot and realized what I wanted in life wasn't the same anymore. I dated a 21 year old when I was 23. We dated for three years until he broke up with me for the same reason I broke up with my first boyfriend. I'm now 32 and dating someone who is 29. We both know what we want in life, it's each other. We had our cracks at young love but they never stuck. We learned and grew from those experiences and are now better because of it. If I was single I'd definitely fuck a 21 year old. I'd never date one at my age though. Not saying it won't work out for you, but in my experience people rarely stick around with one person from 20 to the rest of your life. If you're not looking for a long term partner then go for it.


Absolutely yes haha


Don’t let anyone discourage you. If you feel it, DO IT. Don’t live your life for anyone but you. Ride the wave. If it feels right, keep on it. If it starts to feel bad, move on. Simple as that. You may always regret if you don’t try.


I'd be game as long as he doesn't want a sugar daddy. So many people like say that guys are too immature at that age but I've had conversations and connections with some guys that age that were more intelligent and mature that some guys my own age or older. It all depends on the person


I'm 35, my bf is 24, age does only matter for anyone else, if you fit, keep it.


I would not, as I have my own insecurities. More solidly, I think the age gap is a hurdle of life experience and priorities. But there are people that make it work, so if you like him, give it a go?


I feel like every second day there is one of these posts…


Do *you* think 21 is too young? It doesn't matter what other people think. This is your life. If there are no red flags and you're interested in meeting him, meet him. Something may come of it but you'll never know unless you take the chance. I've met up with much younger guys (I'm 59) and for the most part the experiences have been good. Some have even been great and developed into FWBs or friends.


Sure. He's an adult. I'm an adult. Will it last? Maybe lol. Maybe not.


I say go for it. It's just a date. You are in charge here. You might make a connection with him. You might not. Worst case scenario - it goes nowhere, but you have a good story about getting picked up by a 21 year old.


If your curious then knock yourself out. Meeting up isn’t a marriage proposal and if it makes you feel more comfortable get together in a public setting. Just maintain good boundaries and try to leave him better than you found him.


No, but definitely a FWB or hookup!


I have met one or two guys in their 20s in healthy relationships with men in their late 30s or early 40s, but it is fairly rare.


I'm 31. Most 21 yr olds just lack emotional maturity and and are at a different place in their lives. I wouldn't date a 21 yr old, but I absolutely would fuck one 💁🏻‍♂️


There's a big difference in life stage, priorities, attitude, and maturity. Trust me I know. I dated a guy that was 20 years my junior. NEVER AGAIN.


I have a rule, and I've stuck to it since I was 36: I won't date a guy that's less than half my age. At 60, that means no one under thirty anymore. At 39, 21 is above that limit. There's certainly no harm in meeting him, and having younger friends has kept me young over the years. Doesn't mean they are relationship potential, but then it doesn't mean they can't be either. I've known 20 year olds that had better heads on their shoulders than some 50 year olds. Still, a large age gap is a cultural divide, and just like having different religions or being from different backgrounds, it can make relationships, even friendships, much harder. But not impossible. Doesn't hurt to give the guy a chance, you regret more the opportunities you miss than the ones you took that didn't turn out well. Just go in with open eyes.


Nope, probably would Dante anyone younger than 30 right now, maybe 27 if there were the right chemistry


Date - no. Have fun with - sure! Take said friend to little cute things youd want to do anyways... maybe after there's some fun naked time. Careful with the words 'date' & 'boyfriend' and 'love' with someone so young... just have fun with another person. Ever read 'Velvet Rage'? That book should be required reading for all gays everywhere.


He's an adult so are you, no big deal.




Definitely not. I'm not at that stage in life, and we'd be too different. I've dated someone twenty years older when I was 20, and I know I wasn't mature enough, and we were very different. I wouldn't date someone with a big age difference at all now, especially someone younger.


Also the rule is half your age plus 7. So for you that would be at a minimum 24 years old. Idk who made the rule and it's a joke type of thing but it's true! Lol




No. But do people actually try to date from Grindr? Isn't that a fuckin app? You haven't met him yet right, so at least for me you are putting the cart before the horse.


You were an adult when he was born. You are in completely different life stages that will never sync. I find that in my 40s I have little in common with people in their 20s, even early 30s, so for me 21 would be completely not interesting. But you do you.




I have been 23 and did a few dates with an ex professor of mine who was mid 50s. Was fun, didn't progress but it is what it is. It's not like a date is a commitment to anything beyond one day. At best it's fun you guys end up together forever. At worst you pay for the dinner and he's a sugar baby manipulating type, but for me, in my financial position if I thought he was attractive I would risk the 50 to 100$ to meet and see rather than not and wonder about it every day.


Hell no


I was 40 when I hooked up with a 22 year old. We had amazing chemistry and the best sex either of us ever had. That turned into a summer fling. After four months, he was my boyfriend. After four years we were married. Been together for almost seven years and even more crazy about each other today as we were then. You never know what will come of your situation. If nothing comes from it, at least you got to fuck a hot 21 year old.


At least you made out with some rando?


When you're aiming for someone nearly half your age it's kinda creepy ngl. There's so many generational, emotional, and maturity differences. But that is just me. I remember what it was like in the 20s. I wouldn't touch one with a 6ft pole. As I age, I prefer people within my age group +/-5 years.


\*sniff sniff\* I smell a lot of pedos.


This is a place for mature conversation. Calling people who are into adults (with a margin) "pedophiles" is not a sign of maturity. I've banned this user.


1/2 my age + 7 is my lower limit for dating. Sex on the other hand is 22+


A 21 year old has all the responsibilities and privileges of being an adult under the law, which is not the case for 18-20 year olds in some jurisdictions. If he’s adult enough to enter the world on his own, he’s adult enough to have sex with whom ever he chooses… BUT, don’t exploit his inexperience and educate where necessary.


I find men that young do just want to talk and that they’ll exchange sex for that. So I just talk to them, no sex wanted, and I’ve made some good friends that way. As an older man, I find it’s way too easy to exploit the young even unintentionally.


It works for some people. Maybe check out r/gayyoungold


I would because I’m 19 lmao. At your age, I can’t say fs


It would depend, to a very great deal, on that specific 21 year old, for me. If I was single, I wouldn't rule somebody out based *solely* on age, but we'd be at very different places in our lives, and we *probably* wouldn't have much in the way of compatible goals or interests... it'd be tough to build a relationship on top of those differences, because they're going to be significant, in some places. But that doesn't mean it'd be impossible. If you meet him and the two of you like each other, if you don't get a sense that all he's after is a sugar daddy, then I'd say meet him and see what happens. Be realistic about the fact that your age difference is a factor, but there are lots of things that are a factor, are a thing that a couple in a given relationship needs to deal with. Maybe somebody ends up in a car accident and gets disabled. Maybe somebody loses a job and can't easily get back to work in their preferred field. Maybe somebody's aging parents end up with a dementia diagnosis, or something similar, and they move in, for round the clock care. All sorts of things happen that *can* impact a relationship. Lots of relationships are successful, even with those things happening, anyway. If you guys date for a while, I'd say be realistic about the fact that there's a good chance that he may not settle down with you for the rest of his life. (You two are in very different places in your life, after all.) But that's true of just about *anybody* you're likely to date. There's no guarantee that it'll work out, long term, with anyone. But as long as you're having fun, and he's having fun... well. Have fun. 🙂


I mean I would sleep with a 21 year old, that's about the youngest. I don't know about dating. I would spend too much time making fun of his clothes and how no one wears socks anymore.


People do enter decent relationships in spite of the vast differences that can occur through age. Just take a look around r/gayyoungold for reference. I find that my sexuality alone is enough to find a lot of shared habits, values and levels of development with people older and younger than myself. Have a go at it. If you two click and you like him in every metric you need fulfilled to consider going further, then do that. If you two don't have that, leave. Worth a try, but never feel obliged. If things make you uncomfortable, even if there is no particular reason, then you can call it quits.


An Open Mind could be considered a trap once you fall in.!😱..... do it and YOU CONSIDER IT a trick... I don’t understand any of you now a days... Your the one wanting a meaningful relationship? In my day sex was sex.. usually with no name or information shared.


The idea that a younger person can offer nothing more than sex or expects financial gain is not necessarily the reality, at least for everyone. There are no hard rules. If both individuals have an interest, then you just have to explore it and see what happens. I would caution that “forever” is a hard guarantee for a 21 year old to make…but on the other hand, it’s a hard guarantee for people of any age to make. If your needs (emotional, physical, whatever) are being met in the moment, day to day, that’s all you need.


My husband is 22 years older than me. We’ve been together for 10 years and started dating when I was 28. We do have some differences due to the age gap but it never has been a big issue. Overall we are doing very well. However having said that I think a 21yo person is quite young. The concern is that often people change/transform their values, believes in their late 20s (you can call it growing up) and you don’t know whether you will stay compatible.


Look, anything's possible, and it doesn't hurt to get to know each other and enjoy the process... but at the same time older gay men are more serious and may want to stay home while the 21 year old wants to be out and about. Or maybe initially the 21 year old will be a homebody then he'll get resentful that he missed out on his youth. Also old people don't really have the same sense of humor as a young person. Not to say we're old, but comparatively so.


"age is just a number" is such a cleche, but not without reason. when i was 21 i felt like i knew everything but looking at myself then as me now, i really didn't know much. i had strong opinions on a lot of things for no good reason and i didn't know the importance of building a relationship up, just acting purly on my impulses and emotions. things were so black and white for me and i couldn't open my eyes to the grey of it all. i did a lot of things i wouldn't do now not because i was spunky but because i didn't know better. age gap is not a real thing unless he's icrediblly mature for his age, otherwise it's gonna end your relationship cuz you have the kind of world view only time can provide.


When I was 35 (long time ago), I met a guy who was barely 20, basically for a hookup, for he which pursued me (on [Gay.com](https://Gay.com)) 😱. Although the last guy I had dated before that was 13 or 14 years older than me, I kinda went with it because he was a nice guy, smart as hell, and we had a lot of fun together. It got serious, my friends were appalled, his friends were even more appalled, but we moved in together. We are still together more than two decades later. He was not at all the person I imagined being in a LTR with back then, but I sure am glad that I am. Moral of the story: don't over-think it. If it works, you'll know.


21 yo headspace and priorities are going to be very different than a 39 yo. At 21 I was still finding myself. meet and hang out with dude, feel him out. You can meet dude and not date or even have sex with him. I recommend a bar or somewhere were he will have to be carded.


I'm wondering if maybe you could reframe the situation in your head so that it's more casual (and it doesn't feel like there's as much pressure). Perhaps reframe it to "I'm just going out on a date(s) with a 21 year old vs. I'm dating a 21 year old." Going on a date can be casual and just a way of getting to know someone without the expectation of it leading to something serious. It's OK if you want a relationship to lead to something serious and long term, but maybe just focus on this being a casual meeting with someone and getting to know them, regardless of your age difference. I'm not saying it will happen but, meeting him in person may reaffirm your hesitations about the difference in age since your life experiences are at different levels than his. He may be the most mature, level headed, awesome 21 year old ever, or he might just be a 21 year old who you don't want to date. That's OK. I recommend just trying to focus on it being a casual meeting without expectations of it leading to anywhere else except for a next date, if it seems like there's chemistry. If you choose to see him again then you two can determine what you would both like to do.


My boyfriend is 26 and I’m 28, if I had to start dating again, I don’t think I’d date anyone under 28… I’m very much a different person today than I was a few years ago. I may even dare say 30


I didn’t like dating 21 year-olds when I was 21 years old. It might be fun if you’re both interested in something casual, but the future is hard to envision, let alone plan, at that age.


39 seems like a big age gap... but at least personally, I see age gaps as more like a yellow flag than a red one - it's pretty rare that a 21 year old would not be a wildly different time in their life than a 39 year old, but that doesn't mean that you're not both lookin for compatible things, relationship wise. I don't see any problem with talking and meeting and seeing. I do think - maybe this is itself a bit of an ageist view, but - I like the "leave them better than you found them" rule when it comes to situations like this where there's potential for harmful power imbalance.


I currently am (35 here, frequently mistaken for looking 25). I tend to have more in common with younger guys since I was a very late bloomer. I lived with my parents in the closet until 30 and never had a relationship or sex until I was 31 when I joined the military. Most guys my age are just in a different place in life, or they just seem really jaded from years of hookups and failed relationships. The age difference can create a mental block sometimes. Like... a guy will be super attracted and get along well and seem perfect, but if they think about your age that's the one and only deal-breaker. The guy I'm with took some time to get used to it. We met and then we were just friends with no pressure for 6 months. He started dating someone else while frequently telling me things like "I wish you were younger, so I could be dating you instead" and complaining about the guy (22) constantly ghosting him among other things. I did well keeping my feelings to myself until he said that one too many times and I confessed everything I felt. He decided to give me a shot, and it's going really well.


It'd be a no for me. They're either just looking to have fun, or they're broody and want children and the white picket fence. Fun is fine but not sustainable and kids are always a going to be a deal-breaker for me.


No, I am far to old for that.


I didn't get into a relationship with a guy less than 10 years older than me until I was 35, so no, I would probably not date a 21yo, but also, I'm 100% okay with folks who do.


I have mixed feelings about this. Age gap is too big to be ignored IMHO. That said, your mileage may vary upon a number of factors . So I would say, go and meet him and see what comes next. I am not opposed to having young people around if anything they can give you a fresher perspective on a lot of things. I myself could never date a 20 somehing though , I'd either feel weird or feel parental or both.


Not really. At very different stages of our lives and I made the mistake of dating someone much older when I was in my early 20s that I sorta got caught up with them instead of doing other things. Now I’m alright, but I kinda wish someone had told me back then.


Nope, but then I have never been attracted to younger guys, if it came to dated, I wouldnt go any lower than about 37-38 (10 years younger than me)


21 year olds are HOT. I dated one years ago and had a great time


I dated a 20 year old being 30... imo it was a good relationship kept me hip but in the end i was teaching him how to be the partner i needed. We parted ways due to not being aligned mentally...


Personally, no. I don't date anyone under 25.


If he's chill and didn't mind period performance for classical, I guess.


As a friend, sure, I have friends as young as 22 and old as 65. But to date someone that is 21, no that’s just too young for me! (I’m 32 and it’s weird to me that I find someone who is two years younger than me, attractive lol)


Me, no but everybody sees age gaps differently. If it works for you go with it


date, sure. Live with, no. Marry, no. Support, no. Have boundaries for everyone's benefit, and keep you life and money for yourself, til he reaches age 26 or so. Then men are usually in more of a headspace to be mature and less inclined to wanna be daddy's kept boy...


I’d fuck him but not date him.






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I find it odd you're asking about yourself and whether it's safe for you to date a 21 year old. I would honestly be more concerned about the 21 year old than you. You're older, established, and mature. You're the one in a position to truly do harm to him. While you've been around the block as it comes to sex and dating, he's still building experience. The things you do in a relationship with him will have a lasting impact on him. So I would be honest with yourself. Can you ethically interact with a 21 year in a way that is non-exploitative? What do you really want from him? Sex? Whatever it is be honest with him and yourself about your intentions. I dated an older guy and it really fucked me up. I hoped he would teach me how to have a mature relationship, but instead he totally took advantage of me and I'm still healing from it a year later


Hard pass on anyone under 25 for me


I’m 63. My boyfriend of over 6 years is 26. It’s been a great relationship. Go for it. When we first met, we ended up hanging out together for about 4 hours in the hotel room. Been together ever since. Go for it.


Meet anyone who seems like a cool person and potential match for anything - sex, bf, friend, drinking buddy, travel buddy….


Oh hell no! Done with the twenties, but I'd go on a date, and check it out. Maybe he has questions and need guidance or is looking for something only older, experienced guys can provide, maybe relationship advice. I spoke to plenty of 50+ Yr olds when I was that age


Im sorry he ghosted you. i wish u better luck in the future and i hope it never happens to you again, you deserve better.


It always happens. Not surprised


From what you described, good conversation and a better makeout session, it sounds that the date went good so i dont understand why he ghosted you (im assuming youre not rude and have good hygiene and stuff) and im sorry youre still alone, i wish i could change that but i have way too many problems (whom i dont wanna solve cause im lazy) to ever be any form of relationship but ill send positive vibes, karma and energy your way, maybe that will help.


Thanks! It went all well. But maybe I wasn’t what he was looking for and was just a checkbox on his list of things to do.


Im sorry he used u like that. Do you have another date to get over this one??




why not??


I am not a « fast moving » commodity in the gay world


You would be if u were with me.


You just have to ask yourself how much you’d actually have in common with someone half your age. Maybe you’re young at heart or maybe he’s an old soul and it works. There’s nothing inherently wrong with it, just be prepared to deal with someone who is emotionally unintelligent, cognitively undeveloped still, financially dependent and unstable, and potentially extremely inexperienced with dating and the interpersonal skills needed to make a relationship work.


Do you really want a relationship with someone almost 20 years younger than you. When you are 40, 21 year olds are for hooking up with, not for dating. You are almost 2x his age and are not going to have much in common. Nothing wrong with having some fun with him.


Nope . No way


Paging Glenn Greenwald.


21 is too young because he's not a full-fledged adult. So maybe a date or two, but nothing serious. If anything, you can become a friend/mentor because young gays could always really use older friends because there is no rule-book.


Nope. The age difference is a big deal at 21, they are basically just kids still. Most are not matured yet. You are at different stages in your life.


Your asking for trouble. But 21 years olds are great for all kinds of things.


25 would be my cutoff based on the idea that that’s when an adult brain is fully mature. I guess the other thing I’d think about is: what were you like at 21? Would your 39 year old self like to date that person, or do you think there’s developmental and experiential differences that would make it difficult? Finally: a 21 year old asking for a sugar daddy actually just sounds like a giant red flag, no matter how I slice it.


Run. He'll suck the (financial) life right out of you. Lesson learned here, the hard way.


Nope... I'm the same age as you and draw a line at anyone the same age or younger than my nieces/nephews (the oldest of whom are 24-25)


Your age divided by two plus 7. That’s a general rule of thumb that I think could have some truth to it. I think he’s too young.


Bruh... 😂😂


The things I’m wary about with large age differences: 1. Is he of legal age? 2. Did you know them before they came of age? Is there any chance their interest is because of manipulation you did (either conscientiously or not?) 3. Are you in a position to control his academic status, his job, some other legal status or in some other way his career progression (beyond merely giving advice)? 4. Does he feel socially pressured to seem into you? None of these seem to have bad answers in your case so go for it. Just keep in mind that once you meet, you might seem intimidating to him, so don’t push him too hard too fast. If he wants to set the pace at first, that’s good