Dear Miss A,
I have a crush on someone and I fear we might have made an error. Our second date, like our first, was going amazingly well. Conversation was flowing, we had a great meal and kissed in the car for a time. ...and then, he asked me if I wanted to go back to his place to talk. Originally, I was trying to dissuade him from this idea, to keep our second date on the lighter side, but I wanted to spend some one-on-one time together, so I reluctantly agreed.

To make a long story short, we went back to his place, talked for most of the evening, fell asleep, and seemed to have an enjoyable yet honest exchange. However, as the evening progressed the discussion got into areas neither of us were quite ready to discuss on a second date. Nothing happened on the physical front, but I fear that we might have broken a boundary for both of us, spending too much time together in the beginning of a dating relationship. My suspicions were confirmed a bit, I think, when I received a text that evening saying "thank you for the sweet and intense evening." I haven't heard from him for about three days since and usually we send some small salutation to one another just to say "hello" or some little anecdote to brighten the other's day. I am trying to back off and give us both some space to process.

Admittedly, ending dates has not traditionally been my strong suit with someone I really like, but I want to learn from this and move forward, hopefully with him. I am seeing him again before the holidays to attend a theatrical performance (as we discussed during our last date), but I don't want to make the same mistake twice.

I am guessing I can't say anything to him at this point, but perhaps I can lead with my actions and take the initiative to end things reasonably the next time I see him. How do I end a date in a natural way with him so that we can get to know one another, but retain the boundaries necessary for us to move on in a healthy manner? Where do I go from here?

Thank you,

Carpe Diem Light

Dear Carpe Diem Light,

You should always listen to your gut, and when he asked you to prolong the date, you knew you shouldn't have. Please keep this in mind for the future. This goes to show how drinking more than one or two glasses of wine on initial dates can throw off your judgement. Life teaches. We all make errors in judgement. We're fortunate if we make a mistake once, and learn to prevent making that same mistake. Sometimes we have to make a mistake over, and over again, until we are ready to learn and change our behavior.

Reading between the lines, it sounds like you all hooked up a bit and wanted to have sex, and had a discussion about that. Even though you didn't actually have sex on the second date, it sounds as if it was sexually charged just the same. I think when we open ourselves up a bit too much and feel vulnerable, we need time and space to feel the distance before we can then go back to being with the person to whom we opened up. I think you are smart for backing off, and allowing this man to process what happened and get enough space from you to be able to miss you, and realize he does want to see you again. I'm glad to hear that you all have a date set up for the future, otherwise you'd be worrying that you'd never hear from him again. I honestly think he just needs space right now.