Should She Ask Him Out Again?

Monday | May 11, 2015

Love Letters Divorce

Should She Ask Him Out Again?

I am a separated mom in my late 30s with two small children. I recently reconnected with an old co-worker for dinner. He’s in his mid-40s, never married, no kids. We were casually friendly at work, but even then I had a crush on him. At the time, however, I was engaged, and then got married and started my family. We never socialized outside of work.

Since I left that job, we have exchanged Christmas cards each year for the last four years. A few weeks ago we ended up meeting up for dinner to catch up (we had not seen each other in four years). It was a really nice night and I loved talking with him and getting to know him more outside of a work environment. A few weeks went by and I emailed him to ask him if he’d like to meet up for dinner again. He accepted and we met up again this past week. Again, I had a very nice time with him and he seemed to as well. Both dinners ended with a simple, nice hug. I emailed him to thank him for a nice evening and he wrote back saying he had a great time too, and that although he was busy for the next little bit that he looked forward to catching up again more soon.

He’s an incredibly kind, intelligent, sweet, shy, and a very handsome man. During both dinners neither one of us discussed our romantic relationships or history at all. So, while I discussed my children at times, I never clearly stated that I was separated, but it was sort of implied that it’s just me and the kids. I was afraid of getting into too much personal detail with someone I had not seen in so long – and it’s an emotional topic for me. I was far too nervous to ask if he was seeing anyone, and while it seems that he has female friends, he never mentioned a girlfriend. I don’t think either of us thought of the first dinner as a date, but the second dinner maybe?

Do I wait to hear from him again or reach out again in several weeks and try and make plans with him? Or is his “I want to see you but I’m just busy for the next bit” really just a gentle let down from a nice guy? I don’t want to do some dating dance. I’m just ridiculously clueless when it comes to dating these days, and I’m not someone who’s afraid of doing the asking, but I don’t want to scare him off.

Any guidance you have would be amazingly helpful.

– Third Dinner?

Try not to obsess. Don’t even think about attempting to read his mind. Just take him at his word and assume that he wants that third dinner.

In the meantime, see if you can continue the conversation. Email isn’t just for dinner requests and thank yous. You can send him a note asking about work or something you talked about during your most recent outing. Friends check in. More-than-friends do too.

If/when you get to the third meal (and yes, you can ask for another date if he doesn’t initiate), please tell him you’re separated. You say you don’t want to do the “dating dance,” but you should also avoid the “information dance,” where you waltz around your personal history and force each other to make guesses without asking questions. It’s time for some transparency.

Clarification is scary because of the possibility of rejection, but that’s dating. You can only avoid the answers for so long. It’s better to be clear, especially when you know what you want.

Readers? Should she ask for the third dinner? What about an email in between meals? And how can she get clarity?

– Meredith

Divorce