I Saw Her With Some Guy

Yes, I kept this letter long, but I liked the details.

Dear Meredith,

Some background on myself: I am 34 and travel most of the week for work. A couple of years ago, I went through a bad breakup. My fiancee and I were together for many years. She was unfaithful during our engagement and although I never confirmed it, it was probably not the only time.

Since then I have gone out, for the most part by being set up by friends or my family. That said, I've not really met anyone I was exceptionally attracted to. But in the fall I met someone I did feel strongly about -- let's call her Stephanie.

Stephanie is my niece's preschool teacher. Every Thursday, I hustle from the airport to get to my niece's preschool in the 'burbs. If you're wondering what drives me to babysit one night a week, my brother and his family were there throughout my breakup and the mess that followed.

I thought Stephanie was attractive from the start but it took some time for me to be sure I wanted to ask her out, which I did more than a month ago. We went on three dates over three weeks, and it was the first time I felt deeply about someone since my breakup. The last time we went out, I went as far as telling her how my last relationship ended. In this brief but intense period, there has been clear mutual physical attraction and she has expressed enjoyment of our time together and has said she looks forward to seeing me again. There are differences too -- she's 25 and just started her career and living on her own without roommates.

The evening following the last time we were together, I was out with my friends after watching a game. I knew that she had plans with friends from college. You would think we live in a city that is big enough, but I saw her there in the same bar, in a rather intimate state with a guy. I saw her first but she also saw me.

Which brings me to my current confused state. I have to say I felt hurt since it had not even been two days since I told her about what I've been through. That said, I don't think I have the right to feel that way after going out three times. It's like running from zero to high speed and hitting a wall. I have also been questioning myself and many things including our age difference. Does that matter? I never thought of that before but I do now. Is it me or is that how people in their mid-20s play the field?

Since then, I still do my weekly pickup with my niece and have no plans on changing the uncle routine. My first time seeing Stephanie after the incident, she said she would like to talk, which was clearly not feasible given the activity of a dozen three-year olds at her place of work. On my end, I am not really too sure what to say. The attraction is still very much there, and I think about her all the time. The image of her with that guy is just burned into my mind. Do I even pursue this or let it fade?

– I Watch Frozen on Thursdays, Boston


Talk to her, please. Do it soon -- before prolonged silence ruins everything. Like you said, she had every right to be out with that guy. Yes, it was awful to see her with someone else (especially after you shared an intimate evening), but you can get over it. If you keep making more memories together, they'll wipe out the one of her at the bar.

For the record, I have no idea whether this relationship has long-term potential. And I can't generalize about how 25-year-olds play the field (they're all pretty different). All I know, based on your letter, is that you want a fourth date. So go ask for it.

If she says yes, please pace yourself. You see Stephanie every week and she has a relationship with your niece, which might give you a false sense of closeness. In reality, she's still a stranger. It's going to take a while before you know whether she's good for more than just dates.

Readers? Intimate state? How do you get over seeing something that's none of your business? Should he ask her out again?

– Meredith