Can I reach out for a second chance?

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I met someone last fall just after ending a long-term relationship. She was dating someone at the time, so it seemed harmless to meet up as friends. We hung out for a few drinks and some get-to-know-you conversation. It came with a little awkwardness, but I also continued to think about things we discussed for weeks afterwards. I even made some changes to my routine, and my life, as a result. This is exactly what I would like to find in a partner.

It's been a long time since someone challenged me in a healthy way or asked questions that make me think about something differently. It's also rare for me to find someone as attractive lately as I found her to be. Basically, I think she was a great match for me but I wasn't ready to open up yet. I have been working on myself, processing my new reality, and am ready to start dating. I recently heard that she might be single now. It's been almost six months since we met, but we have only exchanged a couple of short texts. Is it too late to ask for a second chance?

– Second Chance?


Ask for a second chance! Tell her you're single and hope she is too! Don't drop hints or talk around you desires. If you want to get to know her and spend more time with her, make that clear.

I keep telling people that I hope this year of isolation, confusion, and boundaries leads to more honesty and clarity when it's safe to move around. I hope people say what they mean, even if it's a simple "I would like to see you again."

Really, taking six months off from conversation makes some sense, if you think about the limitations of the past six months. Many people are coming out of their small pods and saying, "You still there?" Also, if you're looking for a romantic relationship this time around, make sure she knows. You met as friends first, so she might not be sure about your intentions.

I want you to know – because it seems to be a priority – that you can continue to work on yourself, impress yourself, and test yourself no matter what happens. You can also rest a bit during that process. The work never ends – in a good way.

– Meredith

Readers? What does this look like from the other side? What do you think this woman would think about hearing from the LW?