How many times do I have to turn him down before he gets the hint?

Help me, please. I’m a single high school teacher. One of the other teachers in my school has been asking me out for what seems like forever. I always have an excuse, but the last time I just felt cornered and uncomfortable and unable to say no. So we went out to brunch together this weekend, which I thought would be the end of it, but it’s gotten worse. I tried very hard to make sure I was sending friendship signals and nothing else, and I made a point of paying for my half of the meal. Well, he snuck the money back into my coat pocket. And then, despite my stand-offish good-bye, he has sent me two emails and texted me telling me what a great time he had and asking if we can do it again.

I really don’t want to go out with him again, and I think I wouldn’t be struggling so much with this if he weren’t a co-worker. I have to see him every day and I don’t want to hurt his feelings, but I do want to make it clear that we will never date. How can I let him know this without making my work life miserable? Should I talk to him about it or just keep being vague and blowing him off?

This happened to me once–he asked so many times I finally said yes. It ended poorly: lame date (He couldn’t figure out the tip! I was an English major and I can still figure out a tip!), lame good-bye, and then he leaned in and tried to smooch me like we were Johnny Castle and Baby. I was on crutches and in my haste to get to get my face away from him, I lost my balance and almost fell. Of course he was an inch away from me, so he caught me, but still…

It sounds like this guy doesn’t really do “vague,” and it sure doesn’t seem like he’ll ever get the hint. Guys like this are either suffering from some sort of personality disorder or they’re just lame bullies who try to push you into dating them because they know you’re too nice to say no.

STOP BEING NICE. Who gives a shit if he feels bad? He made you feel bad and uncomfortable by not getting the hint after you said no to him 42 times, and he made you feel uncomfortable by forcing you to accept that he was paying for lunch, and now he’s making you even more uncomfortable by asking you out again. I don’t know why women care so much about hurting other peoples’ feelings–you don’t even like him, he’s creepy, so why do you care if you make him feel bad?

You don’t owe him any explanation or discussion. The next time he asks, email him back and say, “Thank you so much for asking, but I’d rather not.” If he texts you, ignore him. If he tries to ask you in person again, say, “Thank you for asking, but I have to say no.” Then smile and move on. And if it continues, talk to your principal or whoever is in charge of human resources at your school. It’s your right to go to work and enjoy your day without some clueless douchebag pestering you.

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