You've met his friends; he's met yours. Now it's time to add fruity cocktails and mix. Short of introducing your parents to his, combining your two sets of friends—especially if they exist in very different worlds—is one of the most nerve-wracking milestones in a relationship. And since summertime is party time, it's probably going to happen in the next month or so. Here are a few steps you can take to make sure it's not a complete disaster.
1. If you sense impending conflict, give a heads-up. If, say, his friends are hedge-funders, while yours run more to the social worker side, let slip to both sides that there'll be no talking politics. If arguments (or worse) erupt, be ready with the Supersoaker. Or you could make sure there's a baby pool filled with Jell-O and have them take their dispute there. Who can hate with a face full of blue ooze? The Frisky: How To Deal With Fair-Weather Friends
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2. Even if you know your friend Aileen would be perfect for his buddy Fredo, refrain from the fix-up. I know it's tempting, but unless you've run a background check on the guy, resist. First of all, it could blow up in your face when they move in together and the guy who used to be your boyfriend's poker buddy turns out to be a philandering cheapskate. (Don't ask.) Even if your friend doesn't blame you, you'll always feel responsible for leading her there. Instead, supply the introduction and walk away. Quickly.
3. Don't force the fun. Nothing kills the party quicker than a host who's part drill-sergeant, part mommy. So, no berating the non-dancers or forcing shy people to talk. No pushing drinks (you never know who's in the program) and for the love of all that is festive, please, no party games. Why do you think everyone hates baby showers?
4. Everyone has a couple leg-humpy pals in their social circle, so in the interest of keeping the peace, try to steer the slutty types towards each other and away from established couples. I had a situation where one of my man's leg-humpier guy buddies was hitting on a gay friend who was there with her girlfriend. My friend was obviously getting offended so I took him aside, told him the deal and warned him to knock it off. Unfortunately, the lesbian revelation had the opposite effect (caveman!), but with three of us baring our claws and giving the stink-eye, he backed off quickly. The Frisky: Beware: You Can Catch Divorce From Your Friends