The Hard Part

So I went on date #3 last night with a guy that I've been on the fence about. I was looking for a sign or a moment or something that told me that he was a guy I should see more of, but none of those ever came. He's a guy who on paper is exactly what I'm looking for. We had great conversation and food, but there was that intangible something missing...

And so now I have to tell him that I'm not interested.

Twice in the past month since I started my dating frenzy, I have had to tell men that I wasn't interested in them. But both those emails happened after the first date, which made it easier (aside: I only ever email the "thanks but no thanks" sentiment - never make a phone call - when it's early in the phase of online dating. I learned this lesson the hard way by being on the receiving end of a very awkward phone call from a guy who was telling me he wasn't interested after two dates. It was awful and left me awkwardly trying to scramble for words in a conversation I wasn't expecting to have, and since them I have only ever used email to deliver that news). 

The challenge here is that I'm nice... too nice, perhaps. Both in person, and apparently also in my "no thank you" emails. After the worst date I have ever been on, my friends (who were sitting right near us) (no, he didn't know) came up to me and said, "So, was it good?!" and when I stared at them incredulously, they said, "But you looked like you were having such a good time!" It was then I realized that I might be too good at faking my enthusiasm while on a date. The thing is, I really do like people, and I enjoy getting to know them and what makes them tick - even the people I am not remotely interested in dating are interesting to me. But I think that my interest in getting to know them as people might often be misinterpreted as interest in wanting to date them and then I get myself into trouble. 

Of the two men I've said "no thanks" to most recently, one was told that I just "didn't feel that extra something" and the other was told that I had found someone else I really clicked with and I wanted to explore where that went. Both emails were written honestly and kindly, and in both instances, the guys came back asking for a second chance (one immediately and one after a few weeks).

I don't think 3rd-date-guy is the type who would beg for a second chance. But I do think he'll be disappointed when he gets this email. And it makes me feel yucky to know that I will be the cause of that disappointment. It won't stop me from writing the email that needs to be written, but it does make me feel bad because I know how crummy it feels to get those emails. 

This is the hard part about dating.