Asking out older man?

I am 36 and have a crush on my kid’s instructor (52). I think the feeling is mutual but not sure. I know I am his type but I think he won’t make a move out of fear for being that “creepy guy” who hits on the single moms. I would assume as a business owner he’d be careful to protect his reputation.

His birthday is coming up so I was thinking of texting him a happy birthday wish along with an invite that if he ever wants to hang out I’d be down.

I want to send a green signal without making the first move.

I am looking for advice from the male perspective on this. How would you (as an older single dad) feel to be approached by a younger single mom? If you were running a business would this make things awkward?

I’m not thirsty, just open. Thanks.

Posted Sep 6, 2026, 3:11 AM UTC

105101
Loading comments…