What is it Like to Date Someone 18 Years Older?

Q: If I’m dating a man who is 39 when I’m 21 what will it be like when I’m 42 and he’s 60?

I’m dating a man 18 years older than me. We have a lot in common and we get along really well. We did break up after 6 months because he felt bad about the age difference and was hesitant to meet my family. I felt there was no future then but after 4 months he came back with the confidence he was missing to work it out. I told my family, but they’re not fond of the age difference (my older brothers think it’s “disgusting”). My friends, while they originally approved are now skeptical since he was acting ‘strange’ about us before.

A lot of people challenge me to imagine what it will be like when I’m 42 and he’s 60? My question to 40-something women is how comfortable would you be with that age difference, especially if you get along really well? Are older men just more appealing when you’re younger or is it a matter of being a young soul or an old soul and a good connection?

I can’t see myself with somebody in their 20s at the moment. I’m finishing college and have a well-paying job lined up. I actually do stuff – I’m active in my field, I don’t party, and screwing around doesn’t appeal to me. I know I can have many more chances to meet somebody, but sometimes I doubt that I’ll meet somebody that I have this many things in common with again. I don’t want to stop just please those around me, so that they can welcome me to their gatherings, and not make me feel like an outcast.

A: Dear 20-something. Don’t worry about your 40s… worry about now! The age difference is more pronounced in your 20s than in your 40s.


Most 40-somethings will tell you that the age difference is much less an issue in your forties. You’re strong enough to know what you want, you don’t care what other people think as much and at that point your social circle will include a wide variety of ages. Somewhere in your 30s common interests prevail over common ages, particularly with so many people having children later. But your 20’s are a life-stage of much growth, change and getting to know yourself.

It’s really now that you need to worry about. You do have so much to experience and as much as you’re more mature than your peers and you think you know who you are, you don’t, at least not well enough to commit to a man regardless of his age. You have some living to do.  Even 40-something women who married the love of their lives in their early 20s wish they had waited.

Even when you think you’re an old 20-something, you’re not. I thought that I was an old soul because I had a lot of bizarre life experiences at a young age that enabled me to grow early and I had to put myself through college. I was supporting myself so I had this sense of being forty when I was twenty. I got married at 24, by today’s standards… young. The main thing I would say now as a 40 year old is that I was incorrect. I was neither old enough to be making those decisions, wise enough or as mature as I thought.” – 40-something, Detroit, MI

I know women who married older men and are happy but we are generally talking in the 10-year range and with men who seem a bit more settled than your 39 year old. Then I know men who married the younger woman who thought she was mature. Case in point, a 23-year old woman who started her own business and felt wise beyond her years and a 38-year-old man. He had his party days and was established in his career and was all excited to play house…for real. But after 6 months, her business grew and with it more opportunities to play out in the real world. She got the bug and wanted to go out, he wanted to go home.  It was a constant struggle. It was just a symptom of the different places they were in their lives and what they wanted. She didn’t think she wanted it but it’s a natural progression in your 20s. It doesn’t mean she wanted to party and screw around. She just wanted to explore and do more, more, more, rather than less.

So two things I see happening to other women to watch out for. You will get out there and start earning money and start seeing the world is bigger and want to experience it …and he won’t. Or, you will get out there and experience his world and start thinking that is where you should be…and start being someone you are not. As one women relates, this could get you into debt if not worse:

I dated a 35 year old guy when I was right out of college. It was hard because I constantly was comparing my life to the life he and his friends were living. Of course they were making 10 times what I was. It not only hurt my self-esteem, as I constantly faced with what I felt I was lacking, but also I ended up racking up a huge credit card debt trying to keep up with what the women his age wearing and doing. It’s okay to date an older man but don’t try to life his lifestyle. In the end he set me free…he knew I had to go live my life. It was the best gift anyone has given me.” – 40-something, Dallas, TX

The biggest issue for you right now is to make sure you are empowered. While most women say it’s great to date an older man…there’s a limit. When you date someone over 30 in your 20s there could be an imbalance of power. Do you try to please him over yourself? Do you seek his approval? Do you usually do what he wants to do? Does he want you to dress or act a certain way? 40-something women caution against the power difference sometimes inherent in a age difference:

“Date lots of guys in your 20’s. Get to know your own body. But don’t date guys too much older because balance of power is off. You may be intimidated and pressured to do things you don’t want to do”. – 40-something, social worker, California

“It was great. I was young and he had a lot of money and took me to amazing places and bought me things and it was wonderful. But in the end, he was controlling. He was just dressing me up and showing me off and wanting me to be there for him at all times. All our friends were his friends. It was all about what he liked. When I started to become more successful in my career the dream started to fall apart…eventually I had to go be me. I mistook the attention for support and love when it was only himself he truly loved.” – 40-something on divorcing an older man

It’s interesting that your question is about the difference when you’re 40 but you  talk a lot about what’s happening now. There is another voice in your head wondering about what this “strangeness” is all about. There is a big difference between a 39-year-old male who has experienced life changes and challenges that have made him mature and one who has only been responsible to himself. Sometimes a 40-year-old male can be just as immature as a 20 year old. They experience delayed adolescence and start dating the young women that perhaps they didn’t when they were in their 20s. As one 40-something male explained to me:

“A guy has to go through adolescence. If they don’t go through it in their teens or twenties because they are studying or working hard or were just a nerd or maybe the girls were all dating older men, then they will go through it when they become successful. A lot of guys are nerds and now they have money and striped shirts and they go through adolescence. Maybe they were short . . . now they are 6’4” based on the size of their wallet.”

A complicated question and complicated answer. A few last parting thoughts from 40-soemting women.

“If you fall in love at 22 you don’t have to marry at 23. Wait.”

“Common interests is not enough”

“Listen to the voices in your head”

“Try to listen to what your friends think” (if they are truly good friends and not just wanting you to be in their world)

And as always, I welcome more advice from 40-something women out there on this subject!!

on Twitter

on Facebook

on Google+