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You Asked: Is He Off Limits?

Dear Sugar,

My sister and her ex boyfriend broke up over five years ago and since then, he and I have remained friends. Once or twice he has alluded to liking me, but nothing ever happened between us. The subject has come up again, and he asked me to dinner tomorrow night. I adore him as a friend and could see that friendship growing into something more, so should I say something to my sister or just wait to see what comes of this date? — Going on a Date Deborah

To see DearSugar's answer

Dear Going on a Date Deborah,

Without knowing any of the details about your sister's breakup or where she is in her life now, I would advise you to be honest with her about your feelings for this guy. Even if things are up in the air, I'm sure she'd appreciate your candor — wouldn't you want her to be forthright if the roles were reversed?

You don't have to go into too much detail, especially since nothing has happened yet, but the more honest you are, the easier this situation will be for everyone involved. Good luck; I hope she takes the news well.


Join The Conversation
Sofia-Soubrette Sofia-Soubrette 8 years
The heart can't help wanting what it wants. It's up to us to figure out if we can live with the consequences.
Lili-Anne Lili-Anne 8 years
you shouldnt date this guy, if i was youre sister ill be definatly feel betrayed, because this is an unwritten rule and you should respect that.
RockAndRepublic RockAndRepublic 8 years
It doesn't matter that it's been 5 years, he still dated your sibling. Let it go.
You should talk to your sister about this before you go any further. This is why I'm glad I don't have sisters.
Louie Louie 8 years
It it's been five years, then surely she wouldn't mind. What's the big deal, everyone's had exes. Talk to her about it first (don't ask her permission, she doesn't own him or you) and if she's cool with it, then it's no-one else's business.
sparklestar sparklestar 8 years
Maybe he has a sister fetish and once he's done having sex with you he won't call again? Cos c'mon... dude screwed your sis.
MissJules5x MissJules5x 8 years
umm cut off contact. i cant believe youd even be considering this.
vmruby vmruby 8 years
Yes he's off limits....I know that I couldn't ever go there. It would feel so unnatural and gross for me.
CoMMember13630786602261 CoMMember13630786602261 8 years
you definatly need to talk to her. I have 2 sisters and I would furious if one of them went on a date with an ex of mine without telling me. Even if I was completely over it. I dont see how it could hurt anything to talk to her about it. But you could loose alot more if you dont.
candace87 candace87 8 years
I'm just going to assume that your sister knows you two remained close friends, and is okay with that fact, so assuming that she probably sees him from time to time when he is with you, if that doesn't bother her then who knows -- it really depends on your situation. I know how it is when outsiders don't know the details and jump to "OMG YOURE SUCH A B***H THATS SOOOO WRONG!!" So I'll give you the benefit of the doubt here and say... only you know your situation right now, so just go on a few dates and if it looks like it might head in that direction, give her a heads up.
khadeekiinsz khadeekiinsz 8 years
Even if that is her ex, that's just completely wrong on so many different levels. You don't need to mess with her "leftovers".
pippins_halfling pippins_halfling 8 years
I feel like this is forbidden territory.
hope2be hope2be 8 years
That's waaaay too close for comfort. I'd not go near it with a 10 foot pole! I can't imagine dating someone my sister had sex with, even if it's like 5 years ago. But if you're that into the guy, talk to your sister. Still thou, it feels totally awkward and weird. Just saying my opinion, but to each her own.
Miss-Senorita Miss-Senorita 8 years
Talk to her about it but I would touch it with a six foot pole.THE CODE EXIST AND IT EXIST FOR A REASON. Personally its too close for comfort and the thought of getting compared in a relationship is not a good feeling but to know he might compare you to someone you know/related to is even more hurtful and not to mention its so many fish in the sea. I like to close it out by saying gross!!!
jazzytummy jazzytummy 8 years
You can't find anyone else to date except someone your sister slept with? EWWWW.
dit-dah-dit dit-dah-dit 8 years
I don't get what the big fuss is with this. It's an ex. And it's the past. I could care less if my friends, and if I had one sister, were to date one of my exes. Why does it matter to girls so much?
lindssaurussss lindssaurussss 8 years
jeez are there no men where you live? would you date a friends ex, if no. then why do you think its ok if its your sisters ex
Deidre Deidre 8 years
I would absolutely, positively, never go anywhere near this situation. She's your sister. Even if it was long ago and they're would just be way too awkward for her (AND you other family members) should you either get into a relationship with him or have it not pan out. Besides, he's been with your sister (ew, ew, ew).
GScott86 GScott86 8 years
I would stay away from him at all costs. It will hurt your sister, you should know that. Would you feel comfortable with your sister dating your ex? Feelings don't usually go away. Exes always complicate things.
Spectra Spectra 8 years
Luckily, my sis and I never did have the same taste in guys, so we NEVER had the same love interests, but if we ever did, I think we'd be very honest with each other about our feelings. We're both married now, but I would never date a guy that my sis had dated because it would be really weird and awkward.
sparkles61785 sparkles61785 8 years
I don't think that you should go on a date with this guy. That's just one of the rules of sisterhood that should not be broken. If my sister did this, I would stop speaking to her. This is so wrong on so many levels. Don't you have any morals?
aimeeb aimeeb 8 years
I would never date my sister's ex, so wrong.
greenapples1987 greenapples1987 8 years
uhmmm, i'm not sure about and what was the break up between them..if it was a nasty fight and they broke things off sour, then i would not stir those feelings! i would ask her how things were in the end for them and if she would be comfortable with it.
oohsexypenguin oohsexypenguin 8 years
Definitely talk to her about it before going on a date with this guy. Even if you're not asking for permission, it's a sign of courtesy and respect.
mamasitamalita mamasitamalita 8 years
talk to her!
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