Hi Meredith, I am having an issue, and even though I know deep down how to resolve it, I guess a little advice couldn’t hurt. I keep in contact with a former coworker from my previous job. He’s much younger than me (I’m in my late 20s) and I always looked at him like a little brother. I could tell he had a slight crush on me, but I was in a relationship the entire time I worked there, so it was not an issue. He never put the moves on me and we enjoyed a nice friendship. We both love sports, so sometimes we would go to games together and grab dinner here and there.

I’ve now been single going on seven months and I’m casually dating. I’ve told him I’m dating and tried to insinuate that he and I are only friends, but haven’t said it explicitly. All was fine until Valentine’s Day when he asked if he could take me out to dinner – it was very clear he wanted this to be a date. I said I was busy and I haven’t seen him since, although we have chatted and he still asks me to hang out.

How do I stop this? He’s a great kid, but hanging out with him makes me feel awkward because I know eventually he’ll want more and I won’t – plus I’m busy as of late and devoting time to seeing him is grating me. It’s not as though I will be upset if I never see him again, and we don’t share mutual friends or anything. I know I should just come out and say we can’t hang out anymore because it’ll eventually hurt his feelings, but I can’t bring myself to do it. I just keep making lame excuses for why we can’t hang out and he’s not taking the hint. How do I end this? I don’t want to be a jerk, as he was always really nice to me and is a nice guy in general. A (big) part of me wants to lie and say my “new boyfriend” (who doesn’t exist) doesn’t feel comfortable with us hanging out, but I have a feeling you won’t be too keen on that one.

– “Little Brother” Not Taking Big Hint