Just say no

I've become aware of a problem I have recently: It is very difficult for me to say no and disappoint people. I came to realize this soon after Dreamy and I broke up, when, after overcoming my initial sadness, I felt a huge sense of relief. It dawned on me that I would have broken up with him much earlier if I hadn't felt bad about disappointing him.

I actually did try to break up with him in early August, on the eve of Ms. Swamp's wedding to the Sensitive Bostonian (now my brother-in-law). I felt weird bringing Dreamy as my date knowing that I'd probably break up with him soon, so, on my friend Miami Nice's advice, I called him and was brutally honest. I told him that I'd still like to go through with our plans to attend the wedding together and go on a vacation together, but I didn't see a future for us. He asked if there was any chance I'd change my mind, and I said I didn't think so. And then he said that he was fine with coming to the wedding and going to Costa Rica, and we did those things, and I pretended to myself that I'd changed my mind even though I hadn't really and even though I often felt that I'd much rather be by myself than with him.

In the end, things worked out fine. His departure for New York made for a convenient break, and I don't regret staying with him for those extra couple of months. In a way it made it easier to remember our relationship fondly, since I had a lot of negative feelings toward him over the summer that dissipated during the early fall. Dreamy wasn't a bad guy; we had a pretty good relationship, even though we weren't right for each other. But I wonder what would have happened if he hadn't moved to New York. How long would I have continued to try to convince myself that maybe I'd start to feel in love with him again? And who did I think I was doing any favors for by staying with a guy who I knew I didn't want to marry? Having experienced several times how difficult it is when someone (La Moustache, the Brazilian) didn't want to be with me but had trouble telling me so, I know firsthand how much easier it would be if they would just say it.

Now I'm faced with the task of disappointing someone again, a guy I've gone out with three times and had an unpleasant, makes-me-want-to-scrub-my-mouth-out kiss with at the end of our third date. I was pretty sure after our first date that I wasn't into him (as were some friends who happened to be in the same bar and were observing our interactions), but I kept going out with him partly to make sure, and partly because it was easier than disappointing him. Now the time has come, because I REALLY can't go through with another one of those kisses, and I've set myself a deadline of 3 p.m. today and pulled out Ms. Swamp's much-used breakup email to revise and send off.

The good news is I'm also dating someone who I like a lot, who is smart and interesting and likes me too and tells me three times before every date how excited he is to see me and wants to make me dinner next week (date #4). I'm excited to see him, too, and to get to know him better and continue adding to the lists of green, yellow and red flags in his section of my Man List. And if I should uncover some red flags in my research, please remind me to SAY NO.