Should women date (much) older men?
Posted on 2026-09-02
Category: Lifestyle
I received a comment from a reader yesterday asking whether it’s okay for a woman to date an older man. Specifically, a lot older, like 15-20 years. This is an interesting question, so I thought I’d discuss it in today’s post.
I’ve dated men who were both younger (one by 13 years, and one who was only 7 years younger), and men who were older. A lot older. My first experience with dating an older guy came when I was 20 and doing a summer internship…one of my co-workers was 42. I thought he was wise and experienced, but it turned out he was just a 20-year old boy trapped in a 42-year old body. My next experience was in my late twenties, when I dated a man 13 years older. Generally speaking, I don’t tend to go for older men, but there was something different about him. I wanted a relationship with him, so I let it progress. Needless to say, it didn’t work out, but I don’t regret it—he was a wonderful man and we had a good time. That counts for something.
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And as for my current situation, I’m dating a man who is 14 years older now, with..eek…two kids. I always filtered out the older divorced dads from my online dating searches, so I’d never thought I’d be dating one! (We met in person luckily, because I wouldn’t have come across him on Match.com.) Sometimes, life takes us to places we don’t expect, but I’m glad I let go of my filters enough to give the guy a chance.
But I digress. For the most part, the men I’ve dated have been around my age. I am skeptical of women who only date older men, in the hopes of finding security or wanting to be a bit more “taken care of” than most. And then there are the guys who are attracted to younger women only for their looks and youthful energy (many men fantasize about being Hugh Hefner, let’s not deny it…). But I think the question of whether or not you should date an older man (or woman), really comes down to the individuals involved. If two people are truly right for each other, age isn’t really an issue. But maybe something else is going on that bothers you? Depending on the situation, here are some questions you can ask yourself:
1. Would I date him if he was younger and less financially secure?
2. Do we agree on basic values (trust, good communication, kindness, etc.)?
3. Is he in good health, and does he take care of himself?
4. If I want children, is that something he wants as well?
5. Is he divorced, widowed, separated? Does he already have children, and am I prepared to form a relationship with them?
6. If he’s 20 years older and never been married or had a significant live-in partner, can he tell me why?
7. Does he have a habit of dating women significantly younger?
I’m just throwing out questions, but it depends on the scenario and the person. If he is right for you, age won’t be an issue. But if you have reservations about the relationship and the guy himself, ask yourself why. Maybe there is something there that isn’t right, and has nothing to do with age.
Readers, let me know if you’ve dated older, and what your thoughts are. As always, thanks for your feedback!