Love Letters: Hot For Teacher (At My Kid’s School)

Hi Meredith,

I am a single mom who adopted my child (currently in elementary school) as a single parent in my early 40s. We have a great life together, but I find myself wanting a relationship as well. I've been doing the online dating thing on and off for many years and have had some recent short-term relationships that never amounted to much.

Earlier this year, my child's after school program hired a new staff member. Henry (not his real name) is divorced with older kids and roughly the same age as me. During the course of the spring, I started to notice that Henry was being flirty with me -- chatty, teasing, physical contact that was not sexual though beyond what I'd seen with other parents or ever experienced with my child's other caretakers. I started flirting back, and by the end of the school year realized that I was interested in getting to know him more.

Under normal circumstances, I would have simply asked Henry out. I hinted, though was never direct, about this with him. I simply got scared, but am now left with a bunch of questions. Should I have been clearer with Henry? What if I said something but discovered that I was misreading him and would now have to see him for the rest of my child's elementary school career? What if he's worried about the same issues, as well as how this might affect his work life?

It's been such a long time that I've felt a spark with anyone, but I don't want to jeopardize my child's school experience (the most important factor here), Henry's comfort level in his place of work, or my ease of coming and going when I connect with the other staff members of the program. Even if he's not overseeing my child's grade, we'd still run into each other a fair amount.

At this point, there's nothing for me to do. But, I've been mulling this over far too much for the last month, including wondering what, if anything, I might do when school starts again. Help!

– Bumbling in Boston

I wish I knew more about your hints. Something tells me that you weren't very clear about your intentions.

Had you written months ago, I would have suggested that you invite Henry to a group outing. I would have told you to bring him out with friends just to see if sparks fly. If he rejected the idea and didn't seem comfortable hanging out after school, you'd know without having to feel awkward or rejected.

You can still try this. You can invite him out for back-to-school drinks. If you have his contact info, you can do it now.

There's risk here, but that's life. It's possible that you'll date Henry and then break up. That would also be pretty awkward. But you're adults. If that happens, you'll make it work.

Most of the time, these risks are worth taking. If you still feel that spark in September, you have to ask.

Readers? Should she avoid this because of school and her child? Should she ask him out on a date or simply a group outing? Should she wait until September?

– Meredith