Q: Dear Ava. I’m nineteen and have the hots for a woman who is thirty. We both work in the kitchen at a restaurant, so see each other about three times a week when we are both on the same shift. Not only do I look up to her because of her experience as a chef, she’s also super hot, even in her whites. I know she’s single, and I feel like we have a good rapport. It even seems like she’s flirting with me. Would a thirty year old ever be interested in a guy my age, and if yes, what would be my best move? -Jonny
A: Hi Jonny. A hot woman who can cook… what’s not to like! I’m sure you look forward to going to work, which is always a great thing. I’ve had crushes on men ten years my junior when I was in my early thirties, so that isn’t strange or an impossible reality at all.
I say go for it, because you know she’s single and you already have a kind of chemistry. BUT… you will want to proceed with caution. Having a crush on a co-worker presents a few possible problems. She may see dating someone from work as inappropriate. If you do get together but things go south, one or both of you may lose or leave the job. And she may be someone who doesn’t like her love life to be on display.
Still… I say go for it because regret sucks. Try to approach her outside the kitchen, maybe before a shift, on a break, or if a bunch of you are out for drinks after the restaurant is closed. This privacy is important, so neither of you will feel embarrassed if she’s not interested. Be casual when you ask her out, suggesting something you know she is interested in. I always encourage men to be attentive listeners to women, so they will pick up on details they can bring back in conversation.
If she responds positively, keep your relationship private or follow her lead. If she turns you down, know that she was flattered and that at least you tried. Also, there are plenty of online dating sites that cater to younger men attracted to older women.
How do you approach an older woman? How do you ask her out?
Need advice on dating, relationships, or sex? SUBMIT YOUR QUESTION HERE, and who knows, you may appear in the next Cougar World newsletter. -xo Ava