This started out as an answer to one of our questions from the search terms, but it got so long I figured it deserved its own post.
male friends and boundaries
Ooh, boundaries. Tricky subject, but what a marvelous thing. I love boundaries, they’re great. In this circumstance it basically boils down to this: Be courteous. Pay attention to the choices you make and the words you use.
First of all, it doesn’t have to be weird or awkward. Yes, you’re technically potential romantic partners, so what? So’s half the world. There is potential awkwardness in spades though, so being intentional about your words and actions is a very good thing. Over time you’ll develop a rhythm, a sense of what works for you, and you won’t have to think so hard about whether XYZ is okay. You’ll just know how you feel about it, whether it works in this friendship or doesn’t.
For a start, don’t ever imply he’s somehow not a man / not a real man / doesn’t count as a man / not a man you’d like to date; that’s ridiculously disheartening when it comes from a guy friend, and it’s no better when done to them. Obviously don’t imply that you want to date them, unless you do, because that would be confusing and weird. But don’t act as though they’re undateable or less-than-dateable, and don’t say things like “there are no decent single men around here” or “why aren’t there any good-looking Orthodox guys?” Ouch. Think before you speak, and don’t try to blow past it by saying “Well, you don’t count!”
Oh, and for heaven’s sake don’t introduce him as “Eusebius who is just a friend and of course I’d never date him.” Yes, I’ve seen that, and it’s demeaning and rude. I know that gossip is frustrating, but pre-empting it by insulting him or by drawing attention to the fact that you’re not dating is not going to help. If someone confuses Eusebius for your boyfriend, smile and say you aren’t dating. It’s not a big deal. In this regard, treat Eusebius like a single girlfriend: speak warmly and respectfully about him, because he’s a cool dude and totally dateable, you two just aren’t interested in dating each other.
By the way, try and keep your signals clear. If you’re a banter-y type, banter with Eusebius the way you’d banter with a girlfriend, not the way you’d flirt with a date. If you’re not sure you can tell the difference, ask your bluntest, most perceptive girlfriend how you’re coming across.
Especially with very young women, I sometimes see a sort of intimate playfulness that’s sweet and meant in fun, but isn’t entirely appropriate—the sort of extended cuddling that excused with “but he’s like a brother!” Seriously, who snuggles like that with an adult brother? Cf. Seraphic on that. I’m all for hugs (hugs are awesome) but if I want to curl up for a while with my head on a friend’s shoulder, I pick a close girlfriend.
It’s a bit different if he’s married, because then you want to pay attention to keeping two relationships healthy: with your friend, and with his wife. Even if you and she aren’t friends, if you’re friends with her husband then you’re more than acquaintances, and you want to be extra-thoughtful. Besides, if you really value your friend, you don’t want to set him up for a fight with the person he values most in the world.
To begin with, while hugging hello and goodbye is usually fine, never do anything unless you’d do the same thing while she was watching. It’s one thing to go bowling just the two of you if you’ve known each other since you met in your 3rd grade bowling league. It’s another if you’re just getting to know each other, especially if things seem a little off-kilter with his wife. If you’re not sure about the dynamic, hang out in groups, or with the spouse included. And—this is a big one—it’s probably a bad idea to be the person he goes to when he needs to vent about his wife. That can create a really bizarre dynamic. He has guy friends, family, a father confessor—you are not his only emotional outlet. Or at any rate you’d better not be, that’s not a healthy dynamic. If possible, get to know her a little. Being friends with one spouse doesn’t mean you have to be friends with (or even like) the other, but it helps if you can see them as a whole person.
If at any point you get a weird feeling about things (whether he’s married or single), just bring another friend along. Text him to let him know that Philonella is coming with you because she hasn’t been to the movies in forever, or because you thought the three of you could have a really awesome chat about Tolkien. Having Philonella around can take an edge off the awkwardness, and she can also tell you if there are observably-weird undertones.
Also…talk to him. If he really is a friend, have a conversation about what works and what doesn’t. If you value the friendship, then bother to communicate.