How Do We Handle Our Overly Flirty Friend?

We have this friend, a former fraternity brother of my boyfriend’s, and he’s a great guy, but he can’t seem to leave our female friends alone. When we invite him over, he attaches himself to at least one of our lady guests, ignoring all signals of disinterest, and follows her around all night. If he doesn’t get a phone number, he asks us the next day. We’re beginning to think this guy is too lazy to join Tinder and that he just uses our parties as his personal dating service. On the rare occasion he hits it off with one of our friends, it never goes past the second date. Awkwardness ensues, and we end up playing a game of Him-or-Her for our next party. How can we keep him from using our place to troll for girlfriends?

Not a Matchmaker

Dear NaM,

He sounds awesome. (Just kidding.) I have an honest question: What’s so great about this guy? Once you’ve figured out why (or if) you really need him at your parties, I can answer your question.

You mention Sir Creeps-a-Lot* is a college friend of your boyfriend’s. Do I detect a hint of irritation? Does he have to be included because they’ve known each other forever? If your boyfriend’s willing, it may be time for him to switch to guys’ night with his old pal. Sir CaL probably needs a wing man, and your beau can enjoy reliving the college years. (Yeah, that doesn’t sound like a lot of fun to me, either, but everyone’s got their thing.)

Before you decide how to handle it, ask yourselves if he’s annoying, slightly inappropriate, or downright dangerous.

• Annoying. You actually like him, and he is nice, just a little clueless and overly enthusiastic. Your friends are adult women and have likely learned to handle unwanted attention in their own way. Maybe your boyfriend can take his buddy out for a beer and give him a few tips on how to play it cool.

• Inappropriate. Is he more touchy-feely than most people prefer? Do his jokes cross the line from naughty to obscene pretty quickly? You might be doing Sir CaL a huge favor by having a talk. If your boyfriend is comfortable doing it, great. If not, maybe it would help to hear it from a woman. Either way, you might start like this.

  “Hey, Creeps, I think it’s great you enjoy meeting new people at our parties. I’ve noticed something, though, and you probably don’t realize you’re doing it. You can get pretty intense with some of the women we know. Can I give you a little advice? Take it down a notch.”

  After the talk, help him out by inserting yourself into any conversation that’s looking a little too intense and helping change the tone. In fact, this is a great chance to hone your own group conversation skills. Need a subject changer? One of my favorites is, “What’s your entry-to-the-dance-floor move? You know, when your jam comes on and you want to dance.” The answers are usually interesting. Or you can ask him to come help you out in the kitchen for a minute, or exclaim, “Look! A bird!” while your girlfriend escapes. Anything to give his target a chance to flee.

• Dangerous. No sugarcoating: How bad is it? If Sir CaL is making your other guests uncomfortable, or if his behavior is too aggressive, you need to take him off the list, or risk losing your other friends. If you’re asking because friends have complained, consider rethinking your guest list. If there’s any chance he’s veering into harassment or stalking territory, this is a no-brainer. Your friends deserve to be safe in your home.

The most important thing to remember in this situation is that a good host makes sure guests are at ease and able to enjoy themselves.

As for the Him-or-Her invitation game? As long as he’s just in the annoying category, you can invite whomever you like, and let them decide. Just don’t lie if your girlfriend asks if he’ll be there, or she may pull a disappearing act as soon as she sees him (and you’ll have missed a chance to invite someone off the much-debated B-list).

*Not his real name. (I hope.)