..Parents
Meeting your mom is great, because it’s typically an easy way to score points. Your boyfriend knows that as long as he speaks highly of you, asks her questions, and doesn’t accidentally use her drapes as a hand towel, Mom will probably like him. Fathers, however, are another matter. Your dad is a dude and has had sex at least once, which means he knows the kinds of things your boyfriend thinks about and the kinds of things you do with your boyfriend—and your boyfriend knows that your dad knows these things. The result is at least slight discomfort and at worst naked terror, no matter how cool or laid back Dad is. So when they first meet, try not to leave them alone together for any longer than it takes you to pee.
...Siblings
Boyfriends tend to love brothers. After all, making friends with them can be the easiest thing in the world, because they’re not just dudes you know, they’re dudes you know who have absolutely no desire to date you. However, brothers have the same capacity to be protective as dads—the difference being that it’s way more annoying when brothers do it. (It’s also intimidating if your brother is older. And jacked. And an avid hunter.) But the trickier relationship is with your sister: After all, she’s a woman who looks and acts somewhat like you, and who also happens to be a total sexual taboo. So if he’s a little standoffish around her, don’t panic—he’s just doing his best to make sure you know he’s not thinking about anything he shouldn’t be thinking about.
...Friends
To be perfectly honest, yes, he’s checking them out. He’s not doing it because he wants to have sex with them—unless you’d be okay with that—or because he’s looking to trade up. He’s doing it because…well, because he’d check out chicks even if he was at a funeral in a burning building. What he’s truly concerned about is getting them on his side. He knows that you’re going to ask them for their opinions of him and that his stock will shoot way up if they like him. So he’ll be trying hard; all you have to do is grease the social wheels. Oh, and if you find yourself getting pissed at how flirtatious he’s being, don’t. He’s just trying hard to be charming so that they give him the thumbs up.
...Ex
Sure, your boyfriend sizes him up to see if he has bigger guns or if he’s losing his hair faster, but unless your ex has a Tom Brady physique coupled with a Robert Pattinson ability to brood, looks really aren’t all that big a deal. Instead, your guy is much more concerned about outdoing your ex in some way. Since you’d frown on him smashing a chair over your ex’s back, your boyfriend probably just wants to make you laugh in front of him. In fact, what you do in front of your ex is far more important than anything your ex does. If you seem nervous or bothered by his presence, your boyfriend will probably assume that you still have feelings. Which you don’t…right?