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Ask Rene: Can I Date My Sister’s Ex-Fiance?

Dear Rene,

Here’s a question for you. I’ve always had a crush on my older sister’s now, ex-fiance. Susan and Matt dated for two years and broke up about a year ago. During a girl’s night out, I ran into Matt at a local bar and we spent quite a bit of time catching up. It felt great because it was like seeing an old friend.

When it was time to leave, Matt gave me a kiss on the cheek and I felt a spark, a connection with him. I know he did too because he told me he was going to call so we could get together. Needless to say, I felt like I was walking on air when I left the bar.

Rene, I really like him but of course, I am worried about how this will all shake out. Is this a good or bad idea? What are the rules when it comes to dating my sister’s ex-fiance?



Dear Sheila:

I think this is a FANTASTIC idea! Listen, when you get married, make sure your sister is your maid of honor and recruit her to throw your first baby shower. Then ask her if she’d be your birthing buddy when you push out all 2.5 kids that you and Matt will have as part of your perfect, happy little family. SHEESH! Really lady? In case you don’t know, that is SARCASM spelled out with a highlighter, in all caps with a red neon arrow pointing at it because apparently your common sense gauge is broken. Here’s how I see it.

IT WILL CRUSH YOUR SISTER: Yes, Matt and Susan are no longer seeing one another but at one time, they had a deep connection and were planning on sharing their lives together. That train jumped the tracks and a left trail of bloody carnage in its wake. A year later, I’m sure there’s a part of Susan that still cares for Matt; in fact, she may still be trying to get over him. You parading him around like you got the best toy from the Cracker Jack box is not going to be conducive to her healing. In fact, it’s ugly and mean, which brings me to my next point…

WHAT’S GOING ON IN YOUR RELATIONSHIP WITH YOUR SISTER? I’m not a psychologist as I have said before but the fact that you would even consider this makes me wonder about the underlying issues between you and Susan. Why are you doing this? You want something the older sister had? Is this your chance to have some crazy power over her? A chance to cut her deep? Because if you start dating her ex you will do just that. She might even find out that you had a crush on Matt  all along. Then how will Susan feel? How will YOU feel? And speaking of motives and underlying issues, what is up with Matt? Why is HE doing this and what makes him think this is okay? Chew on that for just a second and then…

RUN FAR, FUN FAST: This is real life, not Lifetime. This is real emotion with real people involved. I have one sister and when she divorced her first husband, I wanted to kick that cad right in the keister for hurting my sister the way he did. Who knows what happened between Matt and Susan but it probably wasn’t good given that they’re not still together. Look, there are just some things that violate life’s Big Book of Rules and this is one of them.  I’m sure you could make the argument for your personal happiness and you and Matt were destined to be together. I’m not buying it and I doubt your sister will either. The “ick” factor is hovering quite high here. Just don’t do it.

Oh and that “connection” you felt when Matt kissed you on the check? Yeah, that was booze talking. Ignore it. There are tons fish in the sea.  If you care about your sister and her feelings, you’ll cast your net in another direction.

Good luck! Do you have a question for Rene? She has an answer. Click here and fire away!







  1. pattyrowland

    September 28, 2011 at 8:36 am

    great advice gem and right on the money!!!!!! and of course, i picked up on the tone of your 1st paragraph right away!!!!

  2. Amy

    September 28, 2011 at 9:14 am

    Great advice!!! I mean really who even asks such an insane question. I don’t have a sister but I always wanted one and this girl is taking her sister for granted and thinking about a man first not family!!! And like you said real life not a TV show if only life was like a TV show ha my kid would be perfect, my house clean, and I would have money hahaha!!! Anyways what the heck was she thinking seriously!

  3. Irene

    September 28, 2011 at 9:24 am

    Whoa…is this woman kidding??? I am sorry but I don’t need to try out my sister’s old tires—if I did that would say more about me anyway.

    Geesh-how many men live on this planet?

  4. m.e. johnson

    September 28, 2011 at 8:52 pm

    Rat own (right on), Rene. Altho I have heard of a sister saying, “Go on, have at him and good luck wid dat.”

    But Rene, if it’s that fox in the picture… well… gee…

  5. Keith

    September 29, 2011 at 11:03 am

    Um…from a guy’s point of view.

    What better way to get back at the girl who you broke up with. The writer doesn’t give details so not sure if this applies, but especially if she broke up with him, what better way to get back at her.

    From my viewpoint, one reason and one reason only he’s giving that a shot, and it has nothing to do with a long lasting committed relationship.

  6. Mell

    September 29, 2011 at 11:05 am

    Really?????????? Rarely do I like to go in on the one asking the questions, but really lady. NOoooooooooooooooooooo It’s not OK. i don’t care if your sister says it is, it’s not and let’s just forget that you even saw Mat. Sometimes we as women see/feel things we shouldn’t. Sorry but he’s so off limits. This won’t end good unless you don’t want to have a relationship with your sisters and want to make all of your friends, family and parents decide who side they are on.

  7. SoCalGal

    September 29, 2011 at 5:17 pm

    There’s an assumption that the breakup was bad when that may not be the case at all. Even though the couple were planning to marry, it’s possible they both realized it just wasn’t meant to be for them and they parted amicably. Not saying the writer should slide in as a replacement, but if she does, she should at least talk to her sister first. The worst thing would be getting blindsided.

  8. Rene Syler

    September 29, 2011 at 5:24 pm

    @SoCalGal: Thanks for weighing in and I’m glad I’m not your sister, LOL. Bad break-up, happy break-up, as I said in the piece, it’s icky. There are too many other men out there to be sniffing around and picking up big sis’ leftovers. Thx

  9. bon

    October 6, 2011 at 2:55 pm

    Personally I think the advice is off, even a bit mean spirited. I have 2 sisters and a few girlfriends and my approach to such a thing would be to talk to the girlfriend/sister. Not really asking permission, just more like finding out from your sister or girlfriend if they can handle this person being in their life again. If she can’t handle it then you don’t date the guy. I hope always to be a sister and friend who doesn’t stop others from being happy.

  10. Rene Syler

    October 6, 2011 at 3:09 pm

    @bon, I love when people disagree with me; I never claimed to have all the answers. But mean-spirited? Not hardly. The point is, there is no reason to go there, even if sis can handle it (or says she can, just to make her sister happy). Thanks for weighing in, I’m glad you’re here and equally happy I’m not your sister 🙂

  11. Nana

    October 6, 2011 at 4:18 pm

    I haven’t seen anybody ask what the reason was for the breakup. If the marriage was cancelled, was it because he cheated? The saying is if he cheated with you, he’ll cheat on you. She might want to chat up the sister (obviously they’re not that close or she’d know the answer to the above question) to know what happened. I think it’s icky but I know a fam that has a guy who married two sisters and the three of them show up at the reunions like whatever.

  12. Sandy Seale

    October 6, 2011 at 5:39 pm

    I’m with you Rene. I don’t care how the relationship ended its a bad idea to ever get involved with an ex of someone remotely close to you much less a family member…..even if they say they don’t care…it will come back to bite you at some point. Sounds like a soap opera & those never turn out well 🙂 And is it just me but isn’t it gross to think about having sex with someone your sister has also had sex with??? Yes, I’m assuming they did since they were engaged, etc. If not, then I apologize for jumping to conclusions. Wouldn’t that be called “double-dipping”???? Sorry, couldn’t resist. And I agree the connection you felt was just alcohol & raging harmones.

  13. Amy

    October 6, 2011 at 6:50 pm

    I think that you are right on Rene I can’t even believe this woman thought it would be okay or acceptable. How about this life isn’t a movie or TV sitcom where people don’t have feelings. If only life was a sitcom then I could tell my sister in law I hate her and then we would all sit down and laugh about it later. Or my brother in law could keep having no job and having kids with a bunch of chicks and we all just smile and say oh that guy. Or my mother in law would have Alzheimers and it wouldn’t be the only thing we think about. Priorities lady lost of men out there only so many sisters that is all there is to it!!!! Go RENE!!!!!

  14. SoCalGal

    October 10, 2011 at 12:12 pm

    Gee Rene, glad you’re not my sister either. In case you hadn’t noticed, there really aren’t a lot of men out there. As for “sniffing around and picking up big sis’s leftovers”, please note that I didn’t say she should do it, just what to think about if she did.

  15. Rene Syler

    October 10, 2011 at 12:17 pm

    @SoCalGal: Oooh that sounds mean and in case you hadn’t noticed, I was kidding. Hence the LOL. But in all seriousness, the fact is, there is a line that shouldn’t be crossed. I was single for a LONG time before I got married, which is beside the point. If it means crossing that moral line, I’d rather be alone.

  16. authorkckuma

    October 10, 2011 at 1:29 pm

    First and foremost this violates one of the most intimate bonds there are…sisterhood!
    Second, where in this scenario has this man indicated that he is interested in a relationship with you. You have based a relationship on this mythological world you have created in your head. Really? He was nice enough to sit down and talk with the little sister of his ex- fiance in a bar. He also gave you a customary kiss good night on the cheek and his number. In what world does that say he is interested in a relationship with you. Reminds me of that movie “He’s just not that into you” Get a grip!!! In no way in any scenario is it OK for you to date your sister’s ex fiance. And for all of those who are saying there is a man shortage. Are you really that desperate for a man that would do this? Broaden your circle if your circle is showing you a shortage of men. Open your mind and eyes to more than what is just familiar to you. Because honestly with the scenario she has given that is all she has with this man he is just familiar. They obvious have nothing in common, including a love and concern for her sister.

  17. SoCalGal

    October 11, 2011 at 7:22 pm

    Rene, I thought you might be kidding, but you can never tell online, even with “LOL”. Still, you haven’t been single in a while (I’m guessing), and my point about there not being a lot of men still holds true. Also, I don’t think the line the girl is contemplating crossing is a moral, it’s a “sister/girlfriend code” line. There is nothing immoral about what she’s asking. Again, I didn’t say she should go for it.

  18. Rene Syler

    October 11, 2011 at 7:32 pm

    @SoCalGal: Well yes, when I say something I mean it. I was single for a long, long time and you know what? I was never desperate enough to hurt my sister the way dating her ex would. Never.Ever. She may not have done it yet, but the fact that she asked means she was thinking about it. And that is deep.

  19. DynamoNatalie

    October 16, 2011 at 12:34 pm

    I agree with authokckuma in that this man has not indicated an interest in a relationship with you, plus “I’ll call you” is one of the BIGGEST lies men tell. I’d like to propose another motive of his, that may not involve getting into your pants. WHAT IF he’s hoping you mention this run-in to your sister? Find out the real reason they broke up. I ended an engagement 14 months ago & left town, and although I have no sisters, only a few girlfriends know the entire story. Talk to her & then put yourself in her shoes. If you think he’s all that, then hearing about his many flaws may be just what you need to realize he’s not this perfect dream guy you’ve built him up to be. There are other guys out there who haven’t professed unending devotion to your sister. Date one of them.

  20. Teri T

    October 16, 2011 at 12:41 pm

    Okay…I wasn’t going to comment because I was thinking that everything that needs to be said was already here. However, there’s one comment that I want to address. With respect to the comments by SoCalGal – I have been single for so long that my friends and I joke about the Dyson I’m going to need to knock the dust off my stuff when I am finally in another serious relationship. It doesn’t matter. I would never date the ex of my sister or anyone that I consider a friend. I would think twice about dating the ex of someone I didn’t particularly like. I agree that it’s difficult to meet and date good men these days, but I also agree that there’s a moral line that I couldn’t cross. I also think that Keith’s comment bears some consideration. What’s the real reason a guy would date his ex’s sister, even if it’s been a year ago. I just think I would feel weird and a little like I needed a shower. But, hey, that’s just me.

  21. Camila

    November 3, 2011 at 9:40 am

    I agree with everyone, I wouldnt personally date anyone my sister dated, but she did kiss my first boyfriend and possibly others. That hurt me a lot. She even asked me once later if they could date saying that they had much more in common, even her asking I took as disrespect(I mean yea better than just simply going behind my back, but shouldn’t she care enough to recognize my feelings??? a yr hadnt even passed in our case and we were planning on getting back together). In our case, he had his sister fetish and was just unfaithful, and needless to say never went back with him and I ended up with trust issues and never wanted to even INTRODUCE my bf to my sister for fear the same thing might happen. When I look at my sisters bf (one im not even attracted physically) but I mentally cross them off a list of not available ever. I can never be more than friends with my sisters bf/ex. Speaking of friends bfs, I think there is slightly a bit more leeway it doesnt hurt as much, but I still say no, but I know some friends that have done it date each other in their circle, I think it’s a bunch of drama but to each their own. You just have to ask is this guy worth possibly losing a friendship? Like others said you shouldnt even have to ask. Most times if me and my best friend liked a guy, we usually just liked him together in our fantasy but never went after him because we knew it would hurt hte other and we knew that our relationship was more important than some little boy. We are now adults and have different circles and meet different people, there’s no way we even fall for a guy on the same radar so no worries 😛

  22. Kris

    November 5, 2013 at 10:57 pm

    Bang on Rene! This happened to me just last xmas 2012. Except the I had just found out I was pregnant with our second child, and my sister is only my sis thru marriage. (grown up together though) I found out via Facebook and had left him due to his controlling ways. I had confided in her and she told me to charge him with assault and that I should go to Church!. I found out on boxing day at a womans shelter far from home. When I found out I was horribly hurt and felt extremely betrayed by both! She had the nerve to tell me that she tried to “tell me I had a good man, and that she tried to stay away” I still no longer talk to her and will probably never,. I was close to her all my life, or so I thought. Anyways my horror story did get worse after that, but to make a long story short,,, I had the baby I was pregnant with, and started my life all over again from scratch! As for her… she is not with him anymore and has moved on to a mutual friends ex fiance! NO MORALS AT ALL! This soo called “woman” needs HELP!

  23. Erin

    September 24, 2016 at 7:15 am

    That girl must be sick in the head for even thinking of doing it. She must have some sort of mental issues. Who cares if the break up was good or bad… The fact is that you just don’t do that!!! Morals and loyalty are something some people never got blessed with.

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Combing the aisles at Target in search of the best deal on Cheerios, it hit Rene Syler like the stench of a dirty diaper on a hot summer’s day. Not only is perfection overrated its utterly impossible! Suddenly empowered, she figuratively donned her cape, scooped up another taco kit for dinner and Good Enough Mother was born.

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