Ask Ava: First Date with an Older Woman

Q: Dear Ava. I’m new to this cougar cub thing, and I’m kinda freaked out. Okay, a lot freaked out!!! It wasn’t something I planned. I’ve never even been on an online date with anyone my own age let alone an older woman. I was happy just talking to women online from home. It felt comfortable, but “Jesse”, the older woman, convinced me to go on a date and told me to surprise her with what we were going to do.

I already cancelled once because I was so nervous, and she was completely understanding and said to get in touch when I was ready to meet. I do want to meet her, I’m just not sure where to take her or what she expects. I’m not good with girls my own age either. Can you give me some ideas of what to do with a cougar on a first date. I’m worried if I don’t make a plan soon, she’ll forget about me. We had really great conversations.
– Tim in Haliburton

A: Hi Tim. First thing: take a deep breath. I can really feel your anxiety, and it pains me to see young guys so stressed out about dating older women, especially if it stops you from trying altogether. Dating should be fun, and the truth is, the more you actually do it, the less of a big deal it will seem, and the more you will enjoy the experience.

Women do like men, even the younger ones, to plan dates. We cougars don’t expect fancy schmancy because we know most cubs don’t have a lot of money. Think about her profile when planning the date. What are “Jessie’s” interests. If she’s sporty and active, plan a hike or a trip to a sports game. If she’s artsy or creative, try a gallery or museum visit. Or if she’s a foodie, take her out for dinner to a new restaurant or a wine tasting event.

These are just some basic ideas. It all depends on where you live and what’s available. Maybe you live near an amusement park, the beach, or a zoo. Anything but the boring old coffee shop will be fine, as long as you make the plans.

Tim, read these two previous posts for more pointers. Have a great time! -xo Ava

How to Gain Dating Confidence
10 Steps to a Great First Date

Tell us what you think

Notify of
Inline Feedbacks
View all comments