Eventually, though, the person's going to either confront you about his intentions, or, if he's already done so repeatedly, you'll get so annoyed at his efforts that you'll end up being a jerk. Either way, you can't string that person along forever, and oftentimes, avoiding his phone calls and attempts to hang out just isn't enough to get the point across. Awkward as it sounds, you need to have a little chat. Here are five ways to turn someone down with kindness:
Meet somewhere neutral.
Most of the time, you can get away with pulling him aside at work or the bar where he "just happened" to bump into you. But sometimes a suitor needs more than a "thanks but no thanks" to get the point. Meet him in a Starbucks, a diner, or any other venue that has no significant meaning to either one of you. Just do anything other than knocking on his door or asking him to come over, which might give him expectations of a When Harry Met Sally-style hookup.
Keep it simple and to the point
There's no need to blanket your conversation with excessive apologies and explanations. Don't be wishy-washy. Don't sugarcoat too much. Obviously, you shouldn't say anything outright insensitive like, "I'm just not that into you," but avoid saying too much that might distract from your main point
Send him an email
Sure, it sounds a little passive-aggressive, but it's definitely less awkward than asking to meet him one-on-one only to promptly shoot him down. At the end of your email, offer to talk to him in person if he so desires.
Harsh as it sounds, make it clear that you can't be with him ever. Saying that you can't predict the future, or that something could happen once you're single or emotionally available may prolong his angst and intensify his efforts.
Don't turn the conversation into one about you
Don't you hate the phrase, "for what it's worth, this is hard for me too"? Sure, it's a little awkward to tell a guy to back off, but it's loads easier than dealing with the hurt that comes from rejection. On a related note, stay away from the old, "I don't deserve you, but I know you'll end up with someone great," speech. The heart wants what it wants—goodness knows we rarely crush on the people we actually deserve to be with