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Long before she was married, my sister brought home a tall, successful lawyer ... who happened to arrive at my mother's dinner table with an unsettling, gun-shaped black bag.

Because I'm very protective of my family (and because I'm obscenely paranoid), I considered hiding my assembled family upstairs before he got his rifle assembled, "The Professional"–style. But instead, the guy just put the bag down next to him and started chatting up my grandmother.

When the guy finally went for the bag hours later, it was worse than a sub-machine gun -- it was a magic kit. For the rest of the night, this dude did tricks; silk scarves poured from his shirt collar, and he occasionally showered us with coins. My mother and I were mortified; my grandmother, confused.

In all honesty, he was an all-around nice dude, but it was too late for him. My mom and I had decided that the relationship was over. We told my sister so, emphatically and often. She dumped him shortly thereafter, and I don't feel too terrible about it because it wasn't a love connection, as they say. But if it had been, you can bet I would not have suffered in silence about having to spend my Thanksgivings with Gob Bluth.

It's a horrible proposition, when we don't love the people the person we love loves. But the thing is, I'm pretty sure I've been on both sides of the "Dude, we hate that guy" fence. And I'm sure there's a rational way to deal with disliking your mother's boyfriend or your best friend's girl -- or being disliked yourself -- that don't involve cruel nicknames or waging elaborate prank wars.

Are you with me? Let's be diplomats.

Scenario 1: You Don't Like His Parents
The ways in which your significant other's parents can suck are so myriad the mind positively reels. Mom's icy, Dad's creepy. Mom's distant, Dad's too involved. They're passive-aggressive, or aggressive-aggressive. They're mean-spirited, they're evangelical, they're deeply invested in some terrible basic-cable show, and the fact that you've never seen it does nothing to deter them from going on and on about it.

Your Coping Mechanism
Although I normally advise my friends to be as honest as possible with their boyfriends, there's really no way to be openly negative about his parents without being totally evil. Limit your exposure, and be rational about the fact that we are not our parents, and that your boyfriend is not his father. Or his mother. Unless, of course, the person you're dating doesn't see that his mom is a full-on bear attack in social situations or that his father is a casual bigot, which could signify bigger problems to come for your relationship.
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Look, hardly anyone wants to be judged on their parents, let alone be equated with them, so all you can really ask is that you and the person you're dating are on the level with each other. If the parents are a Legitimate Problem, you need to make sure your significant other is OK with you limiting your exposure to them as much as rationality and decency permit. But if your boyfriend can't understand why you get offended when his mother does quote-fingers when she inquires about your "career," you're setting yourself up for as many fights in the year as there are holidays and family beach vacations.

Bizarro Opposite Scenario:
Your boyfriend doesn't get along with his parents -- but you do. Listen, you've all heard this before, ladies: Don't trust a man who doesn't get along with his mother (with the obvious exception that she's an imbalanced loon). If the parents are cool and their kid is just one of those people who can't stand being happy or approved of, they probably have deeper issues that aren't going to be fun for you to work out.

Scenario 2: You Can't Stand His Siblings
In a way, parents are supposed to be a little taxing. For starters, they're old as dirt and aren't hip and can at least be rationalized by dint of the generation gap. Bastard siblings, however, are much more difficult to deal with, especially if they live in the same place as your boyfriend.

For one thing, siblings have more shared history than you and he ever will, much of which involves old grudges, inside jokes and excuses being made by your partner over why his brother needs to stay with you for a month -- or why his sister is a classic One-Upper who always has a better, crazier, bigger version of the story you just told.

Your Coping Mechanism
If you're dating someone with a just-plain-brutal sibling, all you can really do is accept that you're not going to be close and pull a Neville Chamberlain appeasement situation: I'm never going to like you, but I'll allow you to be crazy and annoying at the margins of my life for the sake of your sibling.

Bizarro Opposite Scenario
Weird as it may be, hitting it off too well with your significant other's siblings can be dangerous ... and not just when that sibling is the gender you find attractive. (Don't even get me started on the potential for horror there.) But if your significant other is like most people, he's always going to be a little competitive with his siblings and need to feel that, at the end of the day, you're on his side. So, as tempting as it may be to be your brother-in-law's best drinking buddy, don't become his closest confidante.

Scenario 3: You Hate His Friends
You know that thing they say about how you can tell a lot about people by the company they keep? Yeah, well, it's true. If you're dating someone whose friends are all obnoxious or boring or rude, you'll want to exit stage right now. If he has lots of nice friends who all just happen to hate you, consider their quorum of dislike and perhaps check yourself for engaging in potentially unlikable behavior. And if you're dating someone with no friends, maybe check his icebox for hobo limbs.

Your Coping Mechanism
A lot of us live in cities or towns away from our families, but friends are inescapable. If you're dating someone whose friends are giant tools, you're looking at someone who is either loyal to the point of masochism or a tool-in-hiding. No one hangs out with racists or idiots or abusive boyfriends unless they, too, have a little bit of that in them, or not enough balls to stand up for the opposite.

Bizarro Opposite Scenario
His "friends" don't really like your significant other, and may even like you more. You know these friends -- the ones who seem to love their pal but casually undermine with comments like "I'm just surprised she landed you," or "You're great -- don't put up with his temper tantrums." This is a coded message. They're telling you they're only friends with the person you're dating because they knew him in high school or because he has a beach house. Run.

In Sum
Remember, in the end the most important thing is that you and your S.O. like each other. Other People can be dealt with, although often with exhausting delicacy. Consider this when deciding whether or not you're in a relationship for the long haul. And hey, if you can take your boyfriend's mom's obsession with "Twilight" and his brother's insistence that authentic spaghetti carbonara DOES have peas in it and his grad-school buddy who calls movies "films" -- it may actually be love.


[Redacted] Guy is the resident single guy writer at Lemondrop. He has written extensively on dating, love and the Wikipedia "talk" page for R. Kelly's "Trapped in the Closet."

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