When You Shouldn't Marry Your Best Friend
I've loved my friend Vincent since tenth grade. He's kind, successful, funny...and gay. We're both 34, and we both want a family. I keep trying to convince him that we have a better relationship than most couples we know. I'm even willing to turn a blind eye if he occasionally needs a male fling, but Vince is scared. I say we can make marriage and parenting work. Am I just being naïve?
— Sharon, Chicago
Sharon, my friend,
Straight, gay, I don't care—you shouldn't need to "keep trying to convince" someone to marry you.
By the way, how exactly do you define "occasionally"? Will you be turning a blind eye two nights a week? One week every other month? Will you make up a story when little Caleb and Violet (yes, I've taken the liberty of naming your children) ask where Dad is? What happens if on one of those fling nights Vincent fools around and falls in love? And what about your sex life? Being in bed with a man who's just not that into you gets mighty lonely...or so I've heard.
Dr. Maya Angelou said that when people show you who they are, you should believe them. Sharon, Vincent isn't scared—he's gay! Thinking you both could be fulfilled until death do you part is naïve at best.
Last year I lent a friend $4,000 to send her daughter to a camp for overweight children. To date she's paid me back $300. Now she tells me they're taking a family vacation to London next summer! What do I do?
— Deirdre, Florida
Dear Patsy...I mean Deirdre,
C'mon, you already know what you have to do. The challenge is to do it without apology. Don't kvetch. Don't ramble. Don't hem, don't haw. You owe your friend nothing. She owes you four grand. Simply say, "Hey, lady, I need my money back by such and such date, so let's make a payment plan." If it means she can't go to London, perhaps she can watch a Hugh Grant movie.
This may sound horrible, but I hate my best friend's kid. He's loud, mean to everyone, and has yet to age out of the terrible twos (even though he's 5). I want to spend time with my friend, but she brings him everywhere. Help!
— Elizabeth, Akron
Dearest Baby Hater,
First let me just say that loud, mean 5-year-olds are dreadful little people, and I'm very sorry that through no fault of your own, you seem to be stuck with one. Could it be he's difficult because his mother keeps dragging him into adult situations that he's not equipped to handle? Is it that she can't afford a sitter? Where's Chucky's dad? (That's right, I'm naming this kid, too.) Is your friend simply hoping that two of her nearest and dearest will grow to adore each other? Might one of them have a bad case of separation anxiety? Could you quickly have a horrible child of your own with whom to torture her? Here's a thought: Given that she's your best friend, could you gently tell her you really miss seeing her one-on-one and ask what's up with Captain Tantrum? If not, try to remember that children grow up, and hard as it is to fathom now, this too shall pass.
Lisa Kogan is O's writer at large and the author of Someone Will Be with You Shortly: Notes from a Perfectly Imperfect Life. To ask Lisa a question, email AskLisa@Hearst.com.