Is a potential partner off limits after your sibling dates them? After running into her sister’s charming ex at the grocery store, one reader writes to the 4-way panel to find out.

Dear 4-Way,
Recently I ran into one of my younger sister’s ex boyfriends at the grocery store. I always thought he was a nice guy, and very handsome, but never gave him much thought beyond that since he dated my sister. They were together for about six months right after she got out of college, then she broke up with him because she met the man she eventually married. I gave him a business card the day I ran into him and he emailed me the next day. We’ve been emailing for about three weeks and last night he asked if I wanted to have dinner with him. I’d love to go out with him, but I’m wondering if that’s weird since he used to date my sister. She always said nice things about him, but my sister can be possessive about things and people, so I’m a worried about what she’ll say. Do I ask her permission? Or since she’s married, can I just go out with him, see what happens, and then mention it to her if things go well?—LB, Indianapolis, Indiana

The Gay Man’s Perspective: Darren Maddox
LB, TELL YOUR SISTER FIRST! Note that I did not say ask your sister. I said tell your sister. Tell her you bumped into him and you’ve exchanged a few emails leading to him asking you out and that you’re considering it. Then ask her if that’s weird. That way, you state your position clearly and you get the upper hand on the possessive. Remember, though, this dude could be a flash in your pants, but your sister will be at every Christmas and Thanksgiving dinner for the rest of your life.

Think of it this way: say you go out with this whippersnapper and you start having a great time together. You love hanging out with him. You’re wearing his favorite shirt on occasion. He makes you laugh uncontrollably. You’re falling in love and the world is a beautiful place. But you have an annoying sense of guilt in the back of your mind no matter where you go. That would be the sister factor and you probably won’t escape the feeling of wondering how your sister will react if/when she finds out. Don’t ruin the best part of dating when you can easily control it with a simple conversation.

As for your sister, the day she got married, she officially took herself off the market and out of the dating pool. If she gets possessive, please remind her of that. If she explodes, give her a chance to calm down while you continue to date the dude. She’ll get over it eventually, and if not, look at it this way: your holidays will always be filled with excitement and drama in addition to fruitcake—like all good family holidays should be.

The Gay Woman’s Perspective: Jody Fischer
I have some questions for you. Do you simply want to be considerate of your sister’s feelings or are you afraid of her getting angry with you? Who’s in control of what you do with your life? Is it you, or is it your fear of your sister reacting?  I’m impressed that you see that you have options. Yes, you may choose to ask her first, or you may wait until after you and her ex start dating. Here’s another point for you to consider: what would you like your sister to do if the situation were reversed?

I just wonder, LB, how much of a hold your sister has on you. You seem pretty clear that she’s overly possessive. How much of a headache has her behavior caused you in the past? I imagine quite a bit since you’re so worried about how she’ll react. I admit, it’s an awkward situation to date your sister’s ex, but if indeed it ended between them in such a clear-cut way and you and he are cool with it, that’s what matters.

My take on your situation is if you’re old enough to seriously date, you’re old enough to not let your issues with your sister take over your life. Do what you think is right and considerate, then have a conversation her. If she gets possessive about some guy that she let go, that’s not really your issue is it?  Meanwhile, enjoy this sort-of new guy in your life. I wish all three of you the best as you all form new points of connection.

The Straight Man’s Perspective: Chris Kennedy
Gee, no sibling rivalry here, is there? You came on to your sister’s ex-boyfriend in a grocery store, flirt with him, and begin a correspondence that’s led you to this predicament. You could have easily avoided this situation, so how concerned are you really with what your sister will say? Do you want her blessing or do you want to make her a little jealous of you … or maybe it’s both? How would you feel if the roles were reversed?

Just curious: would you be interested in this guy if there were no previous connection to your sister? Or is it the fact that he’s a bit taboo that makes him exciting to you?  As you suggested, I would guess that she is “over” him considering she broke up with him and she’s now married. That’s in your favor. Are you really okay with the fact that this guy was sleeping with your sister?

There are plenty of men out there to choose from, so you’re bringing some unnecessary drama into your life with this decision to pursue him. I prefer to get my drama from my television set, not my personal life, but to each her own brand of excitement I guess.  My recommendation is to choose a better date candidate than your sister’s ex. Your pursuit of him is a little twisted, sister, so don’t be surprised if you’re sister’s not going to take it.

The Straight Woman’s Perspective: Rebecca Brown
Listen, LB, you, I, Flannery O’ Connor, and a whole bunch of other single women out there definitely know that a good man is hard to find. But are things so dire that you have to date your younger sister’s cast-offs? I’m sure you’re getting advice from friends (and perhaps other 4-Wayers) that your sister moved on years ago and that your new man-friend is fair game. But I disagree. I stand by my often-expressed opinion that you should never date the exes of friends or family members. Ever. Because it’s weird and awkward, and because he probably had sex with your sister. Eww. Who’s next for this guy when things don’t work out between the two of you? Your mom? Your grandmother?

Of course, you didn’t ask us if you should go out with him. You asked us if it would be weird. (Um, YES!) And you asked us if you should tell your sister first or wait. Clearly, I don’t think you should go out with him at all, but since you probably want answers to the actual questions you asked, I’d have to recommend that you remember that pesky Golden Rule in this situation. How would you feel if your sister, during her single days, breezed in after the fact and told you she went out with one of your exes? Even if you were okay with her going out with him, I’m sure you’d probably wonder why she didn’t bother to ask/tell you ahead of time. So, if you absolutely must go out with this man, yes, ask her in advance. It’s more of a courtesy-ask to make sure she knows you’re trying to honor the relationship the two of you have and operate on the up and up.

But, please think hard about going out with him. You can probably find another handsome, nice man to flirt with—who didn’t date your sister—in your grocery store. And if there aren’t any men, your grocery store will at the very least have Doritos and French onion dip to ease the pain and tide you over until a man comes along that you can create your own story with … one that has nothing to do with your sister.