2003. Someone I met one afternoon at Zeitgeist, generally civilized. Second date after that, dinner. (Yes, I offered to split the bill.) Next day I went on a business trip. He called a few times and emailed once, knowing I was out of town. I called him when I got back and said politely “thank you for dinner, but I’m not feeling it and don’t really care to hang out any more.”

(That’s pretty fucking direct, right?)

The date had been a bit of a disaster—the kind of “I wonder if I can crawl out the bathroom window?” kind of situation. The culminating event was when he asked if I wanted dessert. No thank you—quite full after the appetizer and main, just a coffee. No, really, how about some dessert? No, thanks, I don’t have much of a sweet tooth. Oh but doesn’t this look good? Actually I don’t care much for chocolate. Hmm, I think I may get it, are you sure? I’m sure, just coffee, really. (Waitress comes.) We’ll have the chocolate mousse, with two spoons please.

A couple of days later he sent me a followup email — “let me know if you want to hang out sometime.” I ignored it.

A month after that, he sent me another email, with a poem, saying “how are you? want to hang out? what do you think of the poem?”

So I sent him the following. Which is much more harsh and rude than I ever care to be, but clearly he wasn’t taking NO for an answer.

The Email:

Dear X—

I prefer not to be in touch with you. I was extremely put off by your behavior when we went out for dinner and I don’t want to spend time with someone who treated me as condescendingly as you did.

First, and subtly, you dominated the conversation the entire night. Every time I tried to discuss a topic, you would let me say a sentence or two and then switch the topic back to something you wanted to talk about. This says to me that you don’t care what I find interesting. Moreover, even when the topic was one you had set, you would talk nonstop for minutes at a time. I didn’t feel like I was participating in the conversation; you made me feel like you thought I was there to listen to you, and you didn’t care whether I had anything to say on the matter. When I tried to participate, you would basically ignore what I was saying and then return to whatever point you had been making before. In a word: BORING.

Second, I was appalled at and offended by your behavior regarding dessert. I don’t know how many times I should have to say “No, thank you, I don’t want dessert” for you to understand that *I DIDN’T WANT ANY DESSERT*. As far as I’m concerned, if you say “do you want dessert?” and I say “No, thanks, I’ll just have coffee,” the MOST you should say is “Oh, are you sure? This chocolate cake looks really good…” If, once again, I decline, DO NOT CONTINUE TO ASK ME IF I WANT DESSERT. Your behavior said to me that you don’t think I’m qualified to understand and verbalize my own wants. Then, you seemed to get offended when dessert arrived and I didn’t eat any! Did you think I was JOKING when I said 6 or 7 times that I didn’t want any? Do you REALLY think that I am so illogical, insecure, capricious, and juvenile that I would put on such a show of declining dessert if I really wanted it?? Like, seriously — if I had actually wanted dessert, why would I have tried to obtain dessert by repeatedly insisting that I didn’t want any?? Don’t you think that at some point I would have said “yes, I’d love dessert, let’s share,” or “maybe just a bite,” or “Oh, I’m crazy about dessert, let’s order 3!”? It is insane that somehow my repeated statements that I didn’t want dessert came across to you as “Ellen wants dessert, she’s just not admitting it.” You are not a better judge of what I want than I am.

Finally, I don’t know why you are talking to me. I told you over a month ago that I didn’t care to spend time with you any longer. I deliberately did not respond to the followup email you sent me a day or so later. These were all ways of saying that I don’t want you in my life. NOW I’M TELLING YOU AGAIN: leave me alone.

Maybe if you have communication problems with women [note: his statement], it’s because YOU’RE NOT LISTENING. You treated me like you didn’t care what I said, you didn’t care what I thought, and you didn’t care what I wanted — all of the things that make me a unique and interesting person, you weren’t interested in.

— Ellen

I’m the full-time stepparent of a teenaged boy. He’d gotten it into his head that these kinds of persistent heroics somehow let him “win the girl”. My and his dad’s message to him is consistently: try a couple of times. Ask her out. Maybe ask again just to be sure.

But—and this goes for men and women—you can’t make anyone like you. You can definitely make them dislike you. But no amount of attention or action is going to convert someone’s feelings of “meh” into feelings of “awesome.”

So if you try a couple of times and get your answer, move on. Find someone who appreciates you for who you are. You can’t bully someone into thinking you’re great, and trying is likely to just make them like you even less.