Dating someone younger -- bad idea?

I’m a guy. One of my best friends has been trying to match me up with her best friend (lets call her “Z”) for years. My friend says Z and I are very similar. But both Z and I are rather shy, so we’ve taken a long time to connect.

I’ve gone out to some music and other events with Z. I dismissed the whole idea of dating her because (cough) she’s in her late 20’s and I’m in my late 40’s. But she calls me, we talk, and recently this has felt kind of normal. We have similar personalities and interests. I met her 4 years ago (my friends still thinks Z and I should “get together”).

But I have this prejudice against being an old guy dating a young woman. It’s such a stereotype. But it seems that Z and I really are similar, and get along. She’s smart, nice, can be grumpy like me. I’m self conscious about my wrinkles and thinning hair.

Should I date her? Should we sleep together? How long can I expect it to last? What do you mean by the phrase “we should get together”.

Get together means that you should date her.
I don’t know about this. I’m of two minds: On the one hand, do what you like, to hell with the outside world. Living is about loving. If you two were meant to be together than do it.

The other mind, says: Whoa, be careful. You are setting yourself up for some awkward social situations. Later on in life, the thought of her being a widow might upset you. Also their is a lot of differences between both of your ages. While she’s not just starting out, she’s still rather new to life and she’s going to have more energy than you. Now that that’s been said, I’ll follow up with: It might very well work and none of what my other mind said could be true.

My true feeling is: If you feel as though you could love her, then do so. If it’s a quasi feeling, then explore it more before you commit to anything.

I say go for it. If nothing else, at least you will know.

Me, I say go for it. I’m 37 but for some reason, I prefer the younger ladies. Don’t ask me why. Nothing wrong with it, if you ask me. As long as the age difference isn’t an issue for the two people involved, and they think they can handle the inevitable criticism of others, then why not?

I am in my late 20’s and my boyfriend is in his late 40’s and when we first got together, it was a little awkward (maybe partly because he used to be my boss). But we realized that we really enjoyed each other’s company and it began to matter less and less what other people (mostly HIS peers) thought about our relationship. Now, we are going strong after 2 and a half years and we plan on getting married in the near future.

I say go for it…you can never tell what level of maturity someone is at merely by looking at his or her age. I am pretty mature in a lot of respects for someone my age, and he is pretty immature in some respects for a man his age, so it turns out to be the best possible match for both of us.

I would also say don’t let age be the deciding factor for any possible relationship. I would say use caution to make sure both of you are on the same page about a relationship, though. I wouldn’t worry about the thinning hair and wrinkles, though. If a true bond develops between you two, she will love everything that is “you”, including the signs that you’ve been around experiencing life longer than her. I know that I have been attracted to older men when I was younger, and it was completely based on their personalities and how much fun I had with them. He was wrinkled? I didn’t really notice, because I was too busy laughing and talking.

Well, Im not age prejudiced when it comes to dating, so I would say you should give her a chance.

I have had only one good experience dating someone who was younger than me and I broke up with her for personal reasons. The others I have dated were mostly in their early twenties, about to celebrate the fact they could now legally consume alcohol. They ended up being self-absorbed little twits who required constant attention to the point I felt like I was performing for their sake rather than giving to them out of love. One ended in a messy verbal argument, the other ended awkwardly because some older guy she had a crush on got out of prison (WHAAAAAAAAA) and she promised that she would follow him to the ends of the earth. Yet another was a long time internet relationship that culminated with sex and her stating how she couldn’t deal with me not being open to her fucking other guys. The current apple of my eye is younger than me but not by much, four years, which feels somewhat one-sided. Anyway, that’s why I would vote against dating a younger woman. Go cruise the nursing homes and find a wanton, wealthy widow.

My partner is a good few years older, and we’ve got a good thing going. Give her a chance, don’t let the age gap prejudice you. Good luck.

Thanks everybody for your thoughts. Much appreciated.

My ex-wife was ten years older than me and it was never an issue with us. Although we are divorced now; it had nothing to do with our age differences.

As long as it doesn’t break any of one’s local laws, I don’t see what difference a person’s age makes.

Of course, my husband is 11 years, 8 months, 14 days older than I am. :smiley:

It might not work out, just like any relationship. But while you decide if you want to be together forever, you should take advantage of the fact that you can get it on with a beautiful young person. :wink:

You should also come to terms with what I just said. Taking advantage of the situation isn’t the same as taking advantage of the person. You should treat it like a relationship with someone your own age. Hope for the best, but don’t feel dirty if you end up breaking up eventually. People are people.

You should also consider something else: would you ever date a woman in her late 60s?

I say go for it and see where things lead. If you already have the approval of your peer group, who presumably have your best interests at heart, then give it a shot. If it doesn’t work out, you can always reminisce about the woman half your age who had the hots for you.

Now if she were in her late teens or early 20s, well that’s a little too close to cradle robbing. But if she’s in her late 20s, she’s old enough and mature enough to be making sound decisions about her life, IMHO.

Don’t worry about the age difference! It is just a matter of personal tastes. If you jive together, that’s the important thing.

I think about that. The answer is yes, and I’ve been attracted to women of that age – I’ve talked with them, danced with them, verily, I have flirted with them (and they with me, I believe). They are smart and wise. The thing is, they completely dismiss the idea that a younger man would find them attractive. Women who are only ONE year older than me assume that age is a big issue; they assume that they are undesirable by someone younger. They are wrong.


It depends on how secure you are in yourself, your age, and if it matters, what others may think.

My first husband was 28 years older than me. Some people thought he was my father, some just looked at us funny. Oh well. It wasn’t the age that tore us apart, FWIW.

If you feel there is a chance to make this relationship work - person to person, not as older man/younger woman, then go for it.

Wishing you all the best.


Go for it, I say. My FILs father was 46 years older than my FILs mother!!! In fact, they met because he was friends with her grandparents! When they married, she was 19, he was almost 65. They were married for almost 15 years (until he died), and had one child, my FIL. After that, FILs mother re-married (someone closer to her age that time), and had two more children.

I never knew any of these fine people (although I have read articles in Missouri Conservationist magazine about FILs father, who was an early mover in the conservationist movement), but understand that they had a very happy marriage, and neither of them regretted it.

Best of luck!

If I’m single in my 40s and I can pull a girl in her 20s, I’d be all over it.

Go for it. My ex was 17 years older than me, and our ages were NOT an issue. (His parents, on the other hand, were.)

I’m 38, my SO is 47. Everyone should have as fulfilling and exciting relationship as we do.