Dating Older Men

Read more Relationship Advice and Dating Advice about Dating Older Men

So you want to date an older man? Okay. But first, let’s not confuse this with dating an old man. If you’re into that sort of thing, you’re on your own.

We think the best way to approach this topic is breaking it down by relative age.

If you’re under the legal age—which means you’re in high school— you should not be dating an older guy…period. Most freshman and sophomore boys are harmless enough because they are paralyzed by breasts, walking around like zombies carrying their books in front of their privates hiding what’s obvious to everyone around them. But junior and senior guys are more savvy. Their confidence is attractive to you, but that’s why you need to stay far away. They are like just born nomadic vampires with hypnotic powers they can’t control. You might think you’re mature enough to handle them but you’re not. These guys, no matter how cool they seem, are interested in you for one thing, and we hope you’re at least old enough to guess what that is.

Once you’re in college, the game changes, but that doesn’t mean you’re still better off with someone at least close to your age. Especially be wary of your professor that seems a bit too hip, a bit too accessible, a bit too in touch with young people. His hair isn’t really a bushy mane of black hair, but a mirage of hair dye and developer. And he wears those tinted glasses to cover the dark circles under his eyes, while also allowing him free reign to scan for the most alluring co-ed he can find. And that flashy sports car? It’s nice, but he has little money left over to spend on you. Our suggestion: Best to stick with the geeky science major in the adjacent dorm.

Once you’re out of college and comfortably ensconced in your twenties, dating an older guy might not be a bad thing. Guys take a while to mature, and they lag considerably behind women in emotional maturity by five, maybe ten years. So feel free to trade up. But be careful once again. If he’s more than ten years older than you, he’s likely not looking for “The One.” More like Some One. Or anyone.

Once you’re in your thirties and beyond, it’s all good. Older guys will likely appreciate you for some of your more refined qualities. Your ability to have an intelligent conversation will be just as sexy as a low cut blouse, and it will be refreshing to you to actually have someone look you in the eyes while you’re talking.

If you’ve recently retired and are in your golden years, ignore what we said earlier. It’s likely there won’t be very many older guys around, since most of them will have met their great maker, now sitting around a heavenly poker table playing cards for eternity. In that case an old guy will do just fine. However, you might be surprised if you realign your thinking. You might want to consider a younger man, since he’ll be attracted to your sophistication, and knowledge of the finer things in life. And of course it’s easier than you might think, because afterwards he’ll then be able to brag to his friends about the experience, which is half the reason guys do half of the things they do.

Until next time. This is The Guy’s Perspective.




31 Comments on Dating Older Men

  1. Yes he’s been married and divorced. His ex cheated. He has been divorced for a long time though. The issue was a comment he made about my son and no it wasn’t resolved. It just seems he controlling though. He didn’t get sex when he wanted so he kept it from me the next day! As far as where I meet men the last relationship i had was with someone i met who works for the samecompanys me. I was head over heels for him. We were together two years and he accused me of cheating and kicked me out. I swear I didn’t cheat! My current bf is not very affectionate. He’s laid off work right now and his days are spent at the gym or watching tv. The time we spend is in bed.

  2. @Sonia……So then the question is: What do you like about this guy? From what you describe he doesn’t sound like you’re getting much of what you want. (He’s not affectionate, plays games, immature…..) So what’s the deal? Don’t settle even though it’s hard to meet good guys. They’re out there. Just keep putting yourself out there.

  3. Honestly, he won’t leave. He has a good paying job but he moved in with me. We split the bills and I’ve told him to move. He swears he loves me and isn’t giving up on us. This isn’t the type of guy that has a hard time scoring with women. He has a lot going for him. Maybe he truly does care.

  4. @Sonia…..It’s hard for us to say. You know the situation better than we do. Sometimes it just helps to talk about it. Maybe he really loves you. How do you feel about him? The relationship? Do you want it?

  5. Hi Guys,

    There is this older guy that I met and we are sort of in the stage where we know we can’t date because of the age gap but we want to see each other even though we don’t think it’s a good idea because of my parents and what people would think. It’s not even that we want to date right now, he said I have to be older for that to happen, we just want to see each other and we have admitted that it hurts us both. I don’t know what I should do!

  6. @RP…..What kind of age difference are we talking? How old are you? How old is he?

  7. I’m 22 and the guy I’m seeing is 15 years older. We get along amazingly and have ALOT in common. Unfortunately I still live with my parents and they do not approve of the relationship at all (and I see their side of it, but I have still decided to keep seeing this guy). I reassure them that it’s nothing serious but he recently told me that he is “falling for me”…which just complicates the situation even more for me.So I’m torn between being (happy) with him or breaking it off with him and in order to please my ‘rents. Is there any advice you could give me?

  8. @Niamh……If you were any younger we’d say move on immediately. But it’s hard for us to say. We can totally see why your parents don’t approve. They can see why he’s smitten, but they don’t see what you’ll gain from the relationship. And in general, we kind of agree. You’d probably have more in common with someone who was a little closer to your age. 7 years older and less seems quite standard. Has this guy been married before? Does he have kids? 15 years is a pretty big age difference at least at your age, but it’s not insurmountable. Hmm……. Our advice: Ask your parents to trust you. But keep your eyes open here. He needs to treat you as an equal. This should not be some sort of teacher/student relationship. That wouldn’t be good. Power should be equally divided.

  9. nekkiebee // June 20, 2013 at 6:49 am //

    My boyfriend is 19 yrs older than me i am 24 but he gives me what younger men lack and that’s love and companionship i was ashamed of his age but he doesn’t look 43 at all he still get carded when he buys liquor…should i say forget the age a settle down with three one i know loves me…we been together over a year

  10. I am dating a man who is 32 years older than me. I am 25 years now. Is it okay to marry him?

  11. @Jenny….Well, this isn’t much to go on but sure, why not. 7 years is not that big of a deal at your age. The real question is: What makes you wonder that? If you’re contemplating marriage with this guy, the age shouldn’t be an issue. That should have been worked through long ago. So just by the fact that you’re asking the question makes us wonder about your relationship. What is really making you worry?

  12. Hello! My name is Sheena, I am talking to a guy who is 47 never married no kids. I am 24 we just click so well we have the same interest in museums, movies. and I could talk to him on an intellectual level. He has everything i want in a man education stable job and his own place, me I am working, and have a teachers certificate, while pursing my associates degree in early childhood education, I live with my mother because she is disabled and needs me. Um if we were to take this relationship farther i would, but how would I break this to my mother friends and family. Thank you

  13. @Sheena……..You’re an adult. You have to make your own decisions. That said, we’d take this very slowly. There’s a reason he’s 47 and has never been married and has no kids. Probably because he’s not interested in those sorts of things. If you are, you might want to rethink this. It might be great for a time but we don’t see it turning into a lasting relationship. Good luck.

  14. hi guys, so i met this older man from work. i am 22 and he is 42. he does have 2 kids and has been married in the past. it was weird when our feeling for each other came out on nowhere. we weren’t sure why or how it just happened. we get along so well and we complement each other. is dating someone this much older ok? is is frowned upon? when we are together i feel on top on the world and like i found someone who really does care about me. i am just looking for some advice thats all. please help

  15. @Katie……There is no right or wrong here. Although, yes, in some circles it will be frowned upon. Your family circle for one. But just so you have all the information. It’s unlikely the two of you are looking for the same thing out of a relationship. He sees you as the hot, younger girl he’d like to be with for a time, maybe have sex with, a little arm candy. You see him as the hot older guy who’s much more interesting than maybe some of the younger guys you’re meeting. But understand that it’s not the age that’s the divide, it’s the fact that he’s lived so much more life than you. He’s already experienced many of the things that you might want to experience. He will want to fast forward you, and we urge you to resist that. And typically these types of relationship last for a time until it becomes obvious that they aren’t going to go past the fun and sex stage. Give this some thought.

  16. i realize this but u have never felt this way about a man in my life. it just feels right.. there are butterflies when we hold hands and kiss. i can stare into his eyes and just be happy. we are honest with eachother about everything. he hasnt tried sex at all. i truly dont think thats the only thing he wants from me. i really think there could be something here

  17. @Katie……..We’re not telling you what to do. We’re just telling you what we think from our experience. No two relationships are alike. Just keep those eyes open if you do decide to move forward.

  18. ok i will do. thank you for your help. but when the times comes how do you suggest i go about telling my family about this?

  19. @Katie…….Hmm…..They are not going to be happy about it, but people experiment all of the time, and try out things that may or may not work. How close are you with them? If you’re close, wait until you kind of know what’s going on with this guy and then tell them. If you’re not close, we’re not exactly sure what you should do. It’s always best to be honest. FYI: Your mother might understand more than your father, so start with her. Basically any guy in your family will be upset about it. This means brothers as well. Good luck.

  20. ruth akesime // August 6, 2013 at 11:50 am //

    hi, am 18 and he is 29 . ever since he came into my life, my life changed totally. i told him all about my bad life style and he helped me to stop all those things.i do love him very much and always think about him. and there is no day he does not call me. sometimes calling me more than three times a day when he is at work. everything about him shows he truely love me and i want to spend the rest of my life with him because he is caring more than the younger guys i have dated. and i know he can take very good care of me because he has got everything. all am scared is me coming from a christian home , how my parents are going to accept him because of the age. for me , am ok and dont care about that. and tips on how to make him more happy.

  21. @Ruth……Yes, he is older than you, but you said so yourself, “The younger guys aren’t very mature.” However, that doesn’t mean you jump into a relationship with this guy. Yes, he’s older, but do you know his intentions? What does he want? Usually guys want sex from younger girls. That doesn’t mean he doesn’t want other things, but that’s usually the attraction. Make sure his intentions are true before you commit to him. If he is good to you over a long period of time, your parents will come around. But keep those eyes open. He is almost ten years older than you, and you’ve barely finished high school.

  22. Hi I just want to ask how to handle an older man,my boyfriend is 48 and I’m 26 we’ve been together for 3 years but I still don’t feel safe..I’m still at the point of deciding if I want to get married with him and have kids..but he always mention this to me and ask me if I wanted to start a family with him ,but I’m worried that it may come to the point that he will cheat on me somedayI’m worried about our age gap…you know what the people say about middle age men who cheats…can you give me some advice is it possible that if a younger woman married with an older man is it possible that he will still cheats?do I need to be worry about this or what?and what are the consequences I might face In the near future if I’m married with an older man?

  23. @Christina…Every guy is different. We can’t look into his heart and know. And you know him better than we do. It’s more likely a young guy would cheat on you rather than an older guy. Not that every guy is a cheater, but that’s our experience. Your guy has hit a homerun. He’d be a fool to jeopardize it.

  24. Tarron Finn // April 12, 2016 at 1:43 pm //

    Hi I have been seeing this guy for about a month now and just a few days ago he broke it off… He is 28 and I am 19 (sophomore in college) he told me that he feels I may be too young to be with him, I don’t see age as an issue and my parents are completely fine with me dating him. I’m more confused as to why after taking for a couple weeks and then dating for a month he out of the blue decides that I am to young for him.. Could it be something somebody has told him? Should I press the issue or just let it be? He isn’t the type of person that I’m not going to see around. We have the same group of friends so I see him every weekend…

  25. @Tarron…..This is not an age thing, this is a stage of life thing. If he was say 40 and you were 31, it probably wouldn’t be a big deal. You’d both be graduated from college and working, most likely. Think about it. Let’s say you were dating a sophomore in high school and he wanted you to go to the prom. (Now we know this is not a perfect analogy but you get our point.) You’d probably feel funny about that even if you really liked the guy. As to what happened? It’s hard for us to say. We’d need more info. You’d have to fill us in on the state of your relationship. What sorts of things did you do together? Were you having sex? What were all the friends saying about your relationship? That sort of thing. If you don’t want to share this info in this public forum, you can always choose the Ask a Private Question option on our site. (It does come with a $25 fee but many people prefer that.) If you’re cool with sharing here, that’s fine too.

  26. Tarron Finn // April 13, 2016 at 1:10 am //

    Thanks for answering back… I have no issue addressing our relationship pubically. We were having sex. He works throughout the week and I got to school so when the weekends came around we were inseparable. I’d stay at his hour from Friday till late Sunday night… Everything was running real smooth…. Needless to say I was a little blindsighted by him breaking it off. Our friends were all supportive and happy for us… They never really said much about it and just accepted us dating perfectly….. Again, blindsighted

  27. @Tarron…..We know this feel sudden to you, but the truth is, he probably had doubts from the beginning but suppressed them because he was very attracted to you, and probably wanted to have sex with you, and because you were into him. It’s a powerful thing for a guy to have a woman be into them. It’s a boost to their ego, and it turns them on, even if they know deep down it will never be serious. Our sense is, he had his doubts, but yet, he hoped he could shift his thinking along the way. When he wasn’t able to do that, he broke things off with you. We’re sorry. We know this is really hard on many levels. Did you ask him for an explanation? (Seems that might be the considerate thing to do since he’ll be seeing your regularly with your group of friends.)

  28. Hey guys

    I’m 25 and I’ve begun hanging out with my coworker a lot. He’s about to turn 38. We hang out at work Jim and Pam style (the Office) and we also plan random stuff together. Like he invited me for Endgame. And we are seeing a friend do stand up this week. I’ve told him I’m attracted to him and he told me he is attracted to me. However he said I’m too young for him, he doesn’t want people in his life to think he’s perverted. So I haven’t gone their but sometimes I just wanna rip his clothes off lol. I told him maybe I should hang out with him less so things don’t get complicated but we still end up spending more time with each other than anyone else. I wonder if I should try making a move or bring this up again. A part of me feels like I should leave it alone cause he’s given his answer. But we are in constant communication I mean even our coworkers make jokes about us dating/hooking up lol

  29. @Alisha…..Nice analogy. (Jim and Pam) Sure, he’s definitely older than you, but 13 years is not unheard of when dating. Questions: Do you think his answer is just an excuse because he just wants to be friends? If not, what’s his deal? Has he been married? Kids? What’s his relationship past look like? Long-term relationships? Or is he uptight about this kind of thing? Or maybe you work in a more conservative office environment?

  30. Alisha Nandi // May 11, 2019 at 7:40 am //

    I’ve wondered if he used my age as an excuse cause he’s not that into me, but then we have these moments where it’s like hey one if you guys had to get off the phone or out of the car lol. He has actually dated a handful of women older than him. It’s kind of a preference. His ex was his age though. No kids never married. But he wanted all of that with his ex. He thought she was the one. She was emotionally abusive and manipulative though so the breakup was rough. He told me he had ptsd from it. It’s been a while and he’s over her but still healing from all that went with that ending. I’m definitely not in any rush for anything but I can’t shake liking him. And we always just end up around each other or texting.
    I do remember when we were talking about us liking one another, he said there’s a lot of things we’d have to discuss and somethings I’d need to know about him. He also said that he wasn’t going anywhere.

  31. @alisha…..This seems like one of those “wait and see” situations. Unless of course you ask him directly what’s going on. But that seems premature at this point, especially since you don’t seem to be in a huge rush. That said, if we’re being totally honest, the odds are low that this is going to develop into something serious. That’s just our opinion. Good luck.

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