Make It Stop: I Want a Second Chance at Love!

Last fall, I was talking to this guy “Carl” and we hit it off. We went on a few dates, but I had some heavy issues I was dealing with at the time (an ex-boyfriend who I still lived with, a sister who was going through a divorce, a cousin who had cancer). I told him in October that I just wanted to be friends. He took it hard (I later found out his feelings were much stronger than I assumed). Now, most of my problems have resolved (boyfriend moved out, sister has moved on, and my cousin is in remission) and I’d like to give it another go. Should I try to rekindle what we had, and if so, how I would I go about it? Thank you!

It absolutely seems worth a shot to reach out to him. It sucks the timing wasn’t the best the first time around, but I don’t see any reason to not drop Carl a line now that you’ve got your house in order. The worst that’ll happen is he’ll decline, but you won’t know until you try. It sounds like there’s a good chance he might be willing to meet up and hear you out.

You could say something like, “Hey! I really enjoyed getting to know you and I regret how I left things between us. I’d love to reconnect. Let me know if you’re open to meeting for a drink.” And see what he says.

Whatever happens, expect him to have moved on. That way you’ll be pleasantly surprised if he meets your request with an enthusiastic, “Sure!” You’ve been weighing this scenario in your head for a while, but in fairness to him, you’re dropping back into his life unannounced. Just as it has the potential to be a wonderful event, it can also be disruptive for him. Maybe he just met a new girl or he’s mending his heart from the girl he dated after you. You won’t know until you establish contact with hm.

And if you do meet up for a drink or a cup of coffee, go slow. As much as you’d like to get dolled up with pretty lipstick and rockin’ your most fetching frock, it might intimidate him if you come on too strong at first. While you might be ready to resume your relationship where you’ve left it, his head might be in a very different place.

Whatever happens, you might need to give him a little time to warm up to the idea. Just keep it light, low-pressure, and respectful, and you’ll be fine.

Make It Stop  is a weekly column in which Anna Goldfarb — author of “Clearly, I Didn’t Think This Through” and the blogger behind the blog, Shmitten Kitten — tells you what’s up. Want a fresh take on a stinky dilemma?

Email anna@annagoldfarb.com  with the subject “Make It Stop.” She’ll make it all better, or at least make you laugh. Girl Scout’s honor.