July 27, 2023 at 10:07 am

What Were Your Experiences Dating Older Women? Here’s What People Had to Say.

by Matthew Gilligan

AROlderWomen What Were Your Experiences Dating Older Women? Here’s What People Had to Say.

Have you ever dated a woman who was older than you?

If so, what did you learn?

Was it a good experience or a bad one?

While you ponder your answers to those questions, check out what folks on AskReddit had to say about this.

Start now!

A great relationship.

“My wife was 15 years older than I am.

We were together 40 years till she d**d of cancer. It was a good relationship and marriage.

I know it would not work for everyone but we were happy.”

It was good.

“When I was 30 I dated a 42-year-old.

It was pretty great. She was grounded, successful, easy going, and she knew what she wanted and didn’t want from life.

Eventually, she decided we weren’t working out as a couple, so she made me breakfast, broke up with me very matter of factly, took me to bed one last time, and said goodbye.

It was the best breakup I’ve ever had.”

Going well.

“I’m 33 and I just started seeing some one who is 10 years older than me.

It’s pretty awesome so far, she knows what she wants and tells me what she means.

Plus the s** is outstanding.”

Didn’t work out.

“Girfriend was 19 years older than me.

I was 30 when we met, she was 49. Lived together for over 10 years. she had been divorced twice and had two teenage girls, I became like a step dad. I loved her (and her kids) and wanted to stay together forever. She couldn’t ever get comfortable with the age difference.

Always worried I would leave her for younger woman or that I would want kids. No amount of assurance could convince her I was serious about staying together.

Relationship ended 5 years ago. I miss her and haven’t had any interest in meeting someone new.”

Wonderful!

“I was 21, she was 28. She had an established career, had had enough past relationships to know what she did/didn’t want, and was very direct about it, didn’t play any of the bulls**t mind games I was used to dealing with.

She didn’t care that I was a broke college student, she made plenty of money to take care of herself, we were both just looking to have some fun. Ended up realizing we really liked each others company, one thing led to another, and ~10 years later we’re still happily married.”

An amazing experience.

“She was 14 years older (26/40). One of the best relationships I’ve had.

We split up because we couldn’t come to a consensus on if/what a family was in the cards.”

Winning!

“Dating a mid 40 woman was the best thing that ever happened to me.

She made me feel appreciated EXACTLY for who I am, not trying to change me, or make me feel shit about myself (like a younger 20-something ex-gf used to do).

She is an incredible human being.”

Nice and easy.

“I was 22, she was 44.

We watched Dazed and Confused, had very intimate s**. Then the next day she sent me off with a fresh breakfast and made some strawberry jam granola bars for me for the gym. 10/10, would recommend.

It helped that she and I were both easygoing and she was 8 months out of a divorce and I think also wanted something just casual and fun.”

No games.

“She was 6 years older than me. I was 25, she was 31.

No games, she had her life together.

We were engaged a few moths later and we just celebrated our 17th anniversary a few weeks ago….worked out pretty well.”

Learned a lot.

“Life changing. FWB.

I was 18, she was a recently-divorced 36. She taught me ways to please a woman s**ually and emotionally.

I’m eternally grateful that she saved me from years of clumsy fumbling otherwise.”

Sometimes May-December romances work.

Oftentimes not.