Ok, so I have a male friend, who has liked me for pretty much as long as we’ve known each other, which has been about two years. While there was a bit of an initial attraction, and we went out twice not long after meeting each other, for a number of reasons I ended up being not interested in anything romantic and I gave him the “let’s just be friends” speech (we never even kissed). He took it fine, and in the meantime I’ve since dated other guys and mentioned them to him and he seemed ok with that.
But, I know he still has feelings for me (apparently last summer he called a meeting with a mutual friend to ask what he should do about me!), and when I became single again last spring, he stepped up his efforts to see me and hang out. We don’t live in the same town anymore but he comes to my town frequently and, again, makes a lot of effort to meet up. I accept sometimes and sometimes I don’t, but when I go to where he lives I NEVER try to meet up with him.
So, the real problem is that I am dating someone new, and while I’ve talked about him to my friend, I have been hesitant to call my new guy my boyfriend (for my own stupid insecure reasons), but yet I really feel like he should know that I’m off the market. I just feel bad, and I don’t want to make assumptions or have some awkward discussion with him. Another friend suggested I just say in answer to the last email asking me to hang out “oh, well thursday I can’t because this guy I’m dating is taking me to a concert” or something like that. Too blatant? What should I do?

[I don’t know a nice way of saying this really, but your relationship with this friend is changed probably forever. He sounds like he’s into you and you sound not only uninterested but almost annoyed by his feelings toward you (which already changed the relationship).
I say a phone conversation is more appropriate than an email, and if he is a good friend that is probably more tactful than an email. But be honest about why you feel awkward. The thing is, if he does feel that way you will hurt his feelings.
On the other hand, if you don’t deal with it, sounds like you might end up resenting him.
[This is all his problem and none of yours. He needs to man up and realize you’re not interested and it’s never gonna happen. You have been nothing but clear about this and if he’s still hanging around making himself miserable, he has only himself to blame.
[I totally get where he is on your friend spectrum. I have tons of friends like this: people I hang out with mostly in group or activity settings, but not people I’d ever go out of the way to hang out one-on-one with. Actually, I’d say that the vast majority of my friends fall into this category. (But that’s another story.)
Anyway, because of where he is on your spectrum, I agree with Lex and Shelly above. There is absolutely nothing you need to do about this. In fact, I’d say that avoiding him when he goes out of the way to make plans with you, especially if these are one-on-one plans, is your best option.
He’s not a good friend. Even if he really were just trying to cultivate a friendship (which he obviously isn’t), why try to be more to him than he is to you?
Either way, not all interpersonal issues need to be tackled with Herculean effort. I’d say, just let this one go.
[You need to tell him that you’re seeing someone else, and that you value your friendship too much to take it any further than that. Also, if he can’t be friends with you without having feelings for you and trying to act on them (i.e. if he can’t get over the feelings he has for you), then you need to suggest you not hang out until he can.
I’ve been on his side of this situation on more than one occasion, and while it’s nice to have that hope that some day your friend will come around and see the light, it’s better for everyone involved to get things out in the open.
He’s your friend; you should respect him enough not to lie to him, especially if this guy is going to be a bigger part of your life than someone you just go out with on occasion.
[I have a question first and foremost, has he dated at all during this time? Typically these types of infatuations tend to only last till something else comes along. Fixing him up with someone else lets him know that you want him to move on while at the same time helping him out.
If he has dated during that time, then you’re a fallback crush. Someone that he knows he can obsess over with the worry of being hurt, after all, he knows where you stand.
The thing that kind of bugs me about your initial post is the fact that though he tries to hang out with you when he’s in town, you don’t do the same. That doesn’t sound very friendly. In fact, it sounds down right unfriendly.
I’m sure it because you’re trying to prove to him that you’re not interested and that you’re afraid of leading him on and such, but it’s kind of difficult to say what kind of friendship this is when it seems like neither one of you is treating it as much of a friendship.
That’s my 2 cents.