How To Date a Younger Woman

How To Date a Younger Woman

Tips For Dating Younger Women

You’re dating a younger woman – or maybe you want to – and though you’ve already convinced her you’re not a creep, you’re not totally sure how to should address the age difference. Before you screw it up or scare her away, be aware that there are certain reservations and expectations women in their 20s have about dating older men. Here’s some advice on navigating the years between you – whether it’s five, fifteen, or you’re simply at two different stages in life.


There is a certain curiosity and novelty factor with which women perceive older men, so, if you happen to be one, you have an automatic advantage when you approach a younger woman. That being said, don’t make us uncomfortable by acknowledging the obvious. It’s creepy if our youth is a novelty to you. We will be flattered if you simply treat us as one of your peers. If you’ve said anything like, “Are you even old enough to be here?” or “I’ve got a daughter about your age,” you might as well go home now.


Women are attracted to the confidence of an older man — a quality that boys in our age group often lack. We assume that you know what you want, and we assume you know how to make us feel wanted. So demonstrate those qualities. My friend Joan was in college when she fell for Peter, a professor in his 30s because he was decisive and didn’t play games with her. Plus, he wasn’t afraid to be straightforward about his feelings. Their conversations were more interesting and felt more meaningful than the ones she’d had with past boyfriends. And despite the age difference, Peter allowed her to be the expert when she was one, asking her questions about her photography and culinary skills. That made Joan feel like she was in a relationship with an equal.

How To Date Younger Women


We think the fact that you have all that experience is sexy, but it can also be intimidating. So be direct about things like if you have kids, if you’ve been married, etc. Concealing details like those will be bad news when we find out later. However, while you might be tempted to share all of your wisdom on careers, relationships, and travel don’t scold or lecture. It’ll just magnify the age difference and seriously dull the romance. Lastly, don’t assume don’t assume that women under 30 text only in abbreviations and emoticons. Older guys I meet who text like my sorority sisters come off as inarticulate and insecure.

Also: Tips For Getting Over A Breakup

9_older ladies


I can’t think of anything sexier than a man with a plan. One of the biggest mistakes guys our age make is not taking charge on a date, so this is an opportunity to use your extra years as an asset. Even the loosest itinerary is a welcome departure from a wishy-washy text asking us what we feel like doing. (Unfortunately, that’s very common amongst guys my age.) When my friend 22-year-old friend Marilyn met Rich — 16 years her senior —she had trouble looking past his average looks and round stomach. But Rich took charge and charmed her. He made plans. Marilyn was so impressed by his desire to entertain her that they quickly became serious.

Also: 10 Hot Celebrities Who’ve Been Cheated On

Tips For Dating Older Women


You may be ready to settle down quickly with this girl, but you need to remember that she may not be looking for the same thing. When my friend Laura, who was 23, started dating Brad, who was about 10 years older, she started to feel awkward when he talked at length about the housing market and how so many of his friends were already married. So if you’re dating several years below you, be careful not to make her feel like she has to rush to catch up.


There may be societal expectations or stigmas surrounding relationships with significant age gaps. It is important to be aware of these and to not let them influence your relationship negatively. Instead, focus on building a strong and healthy relationship based on mutual respect and understanding.