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You Asked: Should I Tell My Best Friend I'm Dating Her Ex?

Thu, 01/17/2008 - 5:00pm by DearSugar
1,192 Views - 37 comments

Dear Sugar,

My best friend and I had been close since the seventh grade. Seven months ago, I met her boyfriend. He was cute and funny and great to be with. In fact, we'd talk online every once and awhile. Unfortunately, a few months ago my friend and I had a huge falling out and we still aren't speaking. As of a month ago, her now ex-boyfriend and I started talking much more often and we have developed mutual feelings for each other. They still talk on occasion, but he hasn't said anything to her. Even though they broke up just before our falling out and although it was definitely mutual, I still feel guilty. Should we tell her?

—Crushing and Concerned Cassie

To see DearSugar's answer read more

Dear Crushing and Concerned in Cassie,

This is definitely a difficult situation. When it comes to dating a best friend's ex-boyfriend or crush, the code of rules is really complicated. Half the time we won't allow it, and the rest of the time we find a loophole. My general rule is don't do it unless you are absolutely in love and even that can get you in trouble, but at least it'll be worth it.

Since you and your friend are on the outs, she might see your relationship with her ex-boyfriend as a way of hurting her. Best friends often fight, but many are able to get past their differences in the end. Make sure that before you pursue a deeper relationship with this guy or decide to tell your friend, you're willing to potentially damage your friendship permanently.

Since she's still talking to her ex, it's likely that she'll find out about your relationship sooner than later. Your past fight might be forgivable, but sneaking around with her ex may not be. She'll be angry either way, but if you're direct and honest with her, it might be something you two can eventually work through. Either she'll forgive you or she won't, but at least you can sleep well knowing that you've been honest. Best of luck!

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37 Comments Add a Comment

  • lindholmka's picture
    lindholmka
    1

    I think it's none of her business if you aren't friends anymore and if they've completely broken up. Apparently she is having loads of problems if she is breaking off her relationships left and right so why add more drama to the equation. I don't think it's any of her business and it doesn't really matter if she knows or not because you aren't friends anymore. Not trying to be super harsh or anything. Smiling

    45 weeks 6 days ago Report Comment
  • gossipqueen's picture
    gossipqueen
    2

    I think she implies she wants her friend back, too!

    Tough thing...you won't get her back...you're dating her ex! I say tell her and be honest but be prepared to loose her friendship...like sugar said...now that you guys are not talking THIS (situation) is adding insult to injury.

    but then again...it depends on WHY you guys had a fall out.

    45 weeks 6 days ago Report Comment
  • Masqueraded_Angel's picture
    Masqueraded_Angel
    3

    I say let her find out from him. If you haven't talked to her for months, how shallow would it seem to pick up the phone and say, "Oh yeah, I'm dating your ex...I hope you understand." That would completely wipe away any chance of you two rekindling your friendship, in my opinion. So let her find out from him, since it seems like she talks to him more than she talks to you.

    45 weeks 6 days ago Report Comment
  • frieddumpling's picture
    frieddumpling
    4

    I don't think the situation looks good for you. I think if you value her friendship, you wouldn't be dating her ex so soon after they broke up and not telling her. You should've informed her before you and her ex started dating. That would be the nice thing to do, whether she is understanding is another matter. Now I think you still should be the one to tell her. If she found out from her ex, it just makes you look more of a backstabber.
    Just switch positions with her, I doubt you would be so understanding if you were her. Think about that, then think about what is the right thing to do. The choice is really up to you since you have to face the consequences both ways.

    45 weeks 6 days ago Report Comment
  • brdwaystarlett's picture
    brdwaystarlett
    5

    This is a cardinal sin of female friendships. I agree with Dear on that this is only okay if you are in love. Also, it's important to ask how your best friend feels about the situation. I've been on both sides of the fence with this sort of thing. It's never fun for either party, but if you respect your best friend since Seventh grade, you'll talk to her about it at the very least and make your decision to be with him with regard for her emotions.

    45 weeks 6 days ago Report Comment
  • hotstuff's picture
    hotstuff
    6

    You are so wrong for dating your ex-best friends ex. She's not just any best friend but your bff from 7th grade! It doesn't even matter that you aren't speaking currently. If she was truly your best friend then why are you dating her leftovers? I guess after this relationship he can brag that he had the both of you. Makes me wonder if your falling out had anything to do with him.

    45 weeks 6 days ago Report Comment
  • SBG's picture
    SBG
    7

    I think I have been in a similar situation but in the other side. I had a long relationship with my boyfriend, we even moved together. Then the problems began and he broke up with me. While I was in that relationship I always was a little jealous of my friend because she and my boyfriend got along well. About a year after our break up I found out that they had an brief affair. Even if their affair happened after our break up I could´t but feel that as a betrayal from my friend and from my ex (in the end I was right being jealous of her). Now I have no contact with none of them.

    Even if you are´t speaking right now it seems that you still appreciate her. The situation is that you will hurt her both if you tell her and if you don´t tell and she finds out. Good luck!

    45 weeks 6 days ago Report Comment
  • nevaeh1978's picture
    nevaeh1978
    8

    Let's just think it from her pov.

    Okay..how about if your bff decided to date your ex (who happens to be your 'first' love) and you just broke up with him around a few months, how would YOU feel? Would you love it? Would you be ecstatic?

    I think you're feeling guilty because you FEEL that this is not right. She's your bff since 7th grade! I have no idea why you guys have a falling out, but is this like...you're getting 'one' on her? Or aren't you a bit concerned that you may be the REBOUND girl? It's way too soon for him to be in a relationship with you especially exclusively.

    If you're so insistent on having a relationship with him, at least DATE for awhile first and find out if you LOVE him or not. And if HE LOVES you. If you do and he does, then HE (or both of you) probably will have to break the news to her eventually. Most likely, you won't regain friendship with her, but hey, what can you do. Smiling

    45 weeks 6 days ago Report Comment
  • gal321's picture
    gal321
    9

    ugh there are plenty of men out there, why do people do this?! well no matter how she finds out your friendship with her will definitely not have a chance of reconciliation if youre dating her ex, so think long and hard abt if you ever wanted to be friends again and then act accordingly.

    45 weeks 6 days ago Report Comment
  • RockAndRepublic's picture
    RockAndRepublic
    10

    With friends like you...if you want any chance at a friendship with her, seems like you purposely put a wrench in it by dating her ex. Overall, if you want her, you have to stop messing with her ex.

    45 weeks 6 days ago Report Comment
  • Lovely_1's picture
    Lovely_1
    11

    Oooo very iffy subject.
    The same thing kind of happened to me; but we were friends for WAY longer and I dated the guy for WAY longer too.
    Make sure to tell her to her face. Mine decided to be a coward and tell me over e-mail. I was totally insulted and we haven't spoken since.
    So I would say prepare for the same.

    45 weeks 6 days ago Report Comment
  • lickety split's picture
    lickety split
    12

    lol, guess it's easy to see why you aren't bff's anymore. seriously, with all the men in the world this is the one you HAD to start up with. it was a choice to get with him and you're getting something out of it. ask yourself what that "something" is, because i doubt the answer is innocent, and it seems like perhaps you're both interested in screwing her one last time. not a great basis for a relationship.

    45 weeks 6 days ago Report Comment
  • lellybear's picture
    lellybear
    13

    oh boy. i agree with sugar, if it's love it's love.
    but man, i'd be horrified, crushed, destroyed, heartbroken and every other horrible emotion there is to feel if i were in your former bff's shoes.
    regardless of the terms of what you say is an unfortunate fallout with your friend, if she even so much as loved this guy a little bit....
    oy...
    like others have mentioned, just put yourself in her shoes.
    how would you feel?

    45 weeks 6 days ago Report Comment
  • LovelyLady8's picture
    LovelyLady8
    15

    Hello. I am completely against people that say you are totally wrong for dating a friends ex. I am going to MARRY my friends ex in a short time here. WHATEVER IS MEANT TO BE WILL BE. Honestly, worse things have happened in the world than dating a guy my friend dated. If everyone is still alive and breathing then IT IS GOING TO BE OKAY! I am literally MAD reading this post because someone said.. "This is the cardinal sin of female friendships" PLEASE!! That is so ridiculous. I say go for it. You NEVER know. This happened to me and what if I would have said.. Noo.. you're my friends ex.. I would have passed up the man that I am going to marry. You cannot help where your heart goes. If you turn off your feelings you could have a lifetime of wondering WHAT might have happened. I couldn't deal with that. Don't worry about telling her and go on and live your happy little life. And don't listen to people who say DON'T DATE A FRIENDS EX. ALL IS FAIR IN LOVE AND WAR MY DEAR!

    45 weeks 6 days ago Report Comment
  • wiciltd's picture
    wiciltd
    16

    I would say lovely lady is the kind of person who only sees what it's doing for her and not for other people...How did your friend feel when they found out you were dating their ex??

    Your chances of returning to friends status with this person is slim to none.. So I hope mister ex boyfriend is the best ever because you just ruined a friendship over it..

    45 weeks 6 days ago Report Comment
  • LovelyLady8's picture
    LovelyLady8
    17

    she wasn't happy. and actually she still isn't which is ironic because when i started dating her ex she had a boyfriend for over a year at the time. like i said.. whatever is meant to be will be. you can't control who you fall for. it might not be right and you might end up regretting it BUT YOU ONLY LIVE ONCE! LIFE IS NOT A DRESS REHEARSAL. You will NOT get another chance to DO OVER things that you missed out on. My moms best friend had a boyfriend for about 5 years.. they broke up.. and the next thing she knew he was dating her sister. and he married her. Seriously, like I said as long as everyone is still alive and breathing nothing is THAT bad.

    45 weeks 6 days ago Report Comment
  • Advah's picture
    Advah
    18

    I agree with LovelyLady. Trust me, the last thing I want is finding out my ex is dating a friend of mine (*crosses fingers*), and her friend has all the reasons for being hurt and upset and devastated. But, 1.what is done is done, and 2.as devastated as I'd be in her friend's position, it'd also be terribly selfish to forbid her friend from dating someone she's in love with. Not to mention they're already together, so it's not really gonna change a thing if they break up.

    If you care about your friendship with that girl or can't sleep at night, tell her. But as people said, breaking the news by email or over the phone wouldn't be very considerate - meeting up with her is probably the most honest way to do it. Also, be prepared that it'll hurt her a lot and she'll probably refuse to talk to you, and don't judge her for that. Guess it'll be up to her to decide whether she still wants to be friend with you.

    As for those who say "why him out of all men", well, that's how love works, isn't it. You can decide who you hook up with when drinking too much, but it's not like you decide who you fall for.

    45 weeks 6 days ago Report Comment
  • lickety split's picture
    lickety split
    19

    well anyone who thinks this is "okay" because they are doing the same thing: when you find yourself in this situation you can bless yourself with your own words Smiling karma.

    45 weeks 6 days ago Report Comment
  • Brooklynbee's picture
    Brooklynbee
    20

    I've also been on the other side of this - my ex and my ex-best friend dated each other and I found out about it when other people saw them together. I wasn't speaking to either of them at the time, and it first it upset me a little, but honestly, I wasn't dating him any more (and didn't want to) so they were free to do what they wanted and I forgave both of them. My ex and I ended up being friends - he reached out to me to be friends again. I also reached out to my ex-best friend to try to be friends with her again, although I was not the one at fault, but she didn't respond.

    45 weeks 6 days ago Report Comment
  • Kristinh1012's picture
    Kristinh1012
    22

    You don't even talk to her anymore. Why would you tell her? I don't get it? If you tell her it will look like you are just trying to be a b*tch and rub it in her face that you are with her ex. More than likely she probably really won't want to talk to you after that.

    45 weeks 6 days ago Report Comment
  • popgoestheworld's picture
    popgoestheworld
    23

    I think this is "okay", and it's not because I've done it... I've had it "done" to me.

    The difference? My friend approached me and asked permission. I had moved on, he was a GREAT guy (still is), and she was a GREAT gal (still is). So I told them to go for it! I'm sure it would have been different if he'd dumped me and I was still reeling. But in this case it wasn't an issue at all.

    It didn't work out between the two of them, but I never felt anger at her, or him, for falling for eachother.

    And if it happened to me again, and this time it hurt more? Well too bad for me. Hurt feelings suck, but it's not like once you date a man you own him for the rest of your life.

    45 weeks 6 days ago Report Comment
  • Advah's picture
    Advah
    24

    Thanks for your post Pop, you said very clearly what I couldn't really explain in my post. Smiling

    I don't know why the replies in this thread bother me so much, I think I really can't understand why everyone explains it as a "rule".

    Again, I understand it will probably hurt her friend very badly. But if she decides not to stay with that guy to save her friendship, then she'll be hurt too. I wouldn't say that's a great definition of friendship..

    45 weeks 6 days ago Report Comment
  • erratic-assassin's picture
    erratic-assassin
    25

    I'm engaged to my bf's ex as well...when he approached me it had been a year since they stopped seeing each other. He knew and I knew that if we were going to embark on this journey, it would be for love or nothing. 2 months later we moved in and now we're getting married in August.

    I'm with you on this one LovelyLady. I dont believe in rules. They make me cringe.

    This chick may lose a friend, but who cares? I knew LOTS of people since grade school and now I don't speak to any of them today. Has it affected my life? NO.

    Enjoy your relationship and be happy. And piss on everything else. To those who say KARMA will haunt me, TRUST ME: THIS IS MY KARMA IN RETURN. I deserve this!

    45 weeks 6 days ago Report Comment
  • 7kimba7's picture
    7kimba7
    26

    She will probably find out, since it's a small world. And even if you broke it off with him, she would eventually find out anyway. I think your friendship with her will be done because after all, you had a falling out MONTHS ago and haven't spoken.
    I think you should enjoy your boyfriend and not worry about your ex-friend, because that is spilled milk as far as I am concerned. You can't change what happened, and even if you stopped it now, it still happened in the first place.

    45 weeks 6 days ago Report Comment
  • NYFashionista's picture
    NYFashionista
    27

    I have to admit, I've always found it strange when best friends date each others' exes. I think for me, when I meet my best friend's boyfriend (a best friend who I consider as close to me as a SISTER- and I know many other women are like this) I immediately see her boyfriend as a brother...lol I would never or could never date anyone who I considered to be like a brother. So there you have it. That's my "rule". It works perfectly.

    45 weeks 6 days ago Report Comment
  • jennifer76's picture
    jennifer76
    28

    For the actual question at hand here, I don't know. That's a weird situation. Depending on what your friend is like, if you inform her that you're dating her ex, she may see that as an aggressive and hurtful thing not a compassionate thing. I really think this is a decision you have to make since only you know the people involved and the circumstances.

    For the topic this discussion has evolved into, I think the whole "cardinal rule" thing is ludicrous. If you actually care about your friends, why wouldn't you want them to be happy in their relationships? Why would you try to keep your friend away from someone they care about, simply because you're jealous. Jealousy is an ugly thing.

    And I have been in this situation but from the other side. My ex (my first love and an intense high school relationship) and one of my closest friends started dating a few months after he and I broke up. While I have to admit to twinges of jealousy, I did not feel "betrayed" in the least. He was a great guy and after a string of really crappy guys, she deserved a great guy. And she was a sweet girl and a lot of fun, and he deserved that too. I would have felt horrible stamping my feet and demanding they not see each other for the sake of my ego. Besides, I dated him while I was dating him. I don't own him forevermore.

    45 weeks 6 days ago Report Comment
  • michelleannette's picture
    michelleannette
    29

    tell her. she will find out eventually.

    the timing is unfortunate especially since you're not talking at the moment. maybe before you really get started with this guy you should patch things up with your friend. if he likes you, he'll understand that you need to focus on your friendship first.

    honestly, i wouldn't go for any of my friends exes. there is just too much possibility for conflict and to ruin a friendship. there are plenty of people to choose from.

    45 weeks 6 days ago Report Comment
  • geebers's picture
    geebers
    30

    Exactly - why would you deprive someone else of happiness for someone who YOU no LONGER are dating? That is terrible advice. However, the situation here is different because this isnt a girl dating her best friend's ex while they are still friends. If you and this girl are on the outs- there is zero chance of her forgiving you when you tell her "hey im sorry lets be friends again oh by the way im dating your ex". If you VALUE her friendship MORE than your relationship with this guy - I would take a break from him and try to rebuild it with her. If you and him are meant to be together and are in LOVE not lust -then trust me it will happen later on in time. If you become friends again - at least at this point you have done the right thing and can HONESTLY approach her and tell her you have feelings for him. Then it is her issue if she doesnt "approve" not yours. But if you dont care about her friendship - then you need to move on and just date this guy and realize you have no chance of being friends. Maybe if your friend is mature she will likely forgive and forget but I dont know this situation.

    45 weeks 6 days ago Report Comment
  • Korsgal's picture
    Korsgal
    31

    Why are you dating him in the first place? I assume that you and your friend have a possibility of working thing out and becoming friends again. But now that you're dating this guy, I think it would be hard for the two of you to become friends again.

    45 weeks 6 days ago Report Comment
  • Martini Rossi's picture
    Martini Rossi
    32

    I've never been in this situation (thanks God) but I think you should stick to the rule - Never date your best friend’s ex, whether your still friends or not.

    Since you feel guilty about it I believe that still means that you still care about your friend and have hopes of reconciling with her so dating her ex wouldn’t be a great idea.

    Remain friend with her ex and that it. If that too hard because of the chemistry then break all communication. You need to figure out what’s more important to you - a new bf? Or your old bff?

    Good luck and try not to get yourself in this kinda mess again. No one likes someone else's leftovers.

    45 weeks 6 days ago Report Comment
  • Ashlim's picture
    Ashlim
    33

    My best friend hooked up with my ex within a week of our break-up. I felt especially betrayed because she knew he was horrible to me. When I confronted her about it she told me she didn't want to regret missing out on true love blah blah blah. It only lasted for 2 months. I tried to forgive her when she apologized to me and gave our friendship another try... but it just wasn't the same anymore.

    NYFashionista - I'm the same way! I see my friends' boyfriends as brothers too.

    45 weeks 6 days ago Report Comment
  • Jennifer777's picture
    Jennifer777
    34

    The question you need to ask yourself is: Do you ever expect to talk to your best friend again? If you don't then go ahead and date him, let her find out from him because you calling and telling her at this point would just be class-less... If you do then step away from the ex. He is off limits until you get the ok from her and that is gonna take the 2 of you mending your broken friendship first (and even then you might not get the ok...) Think hard about what you truly want for your future and who you really want in it... Good luck!

    45 weeks 6 days ago Report Comment
  • qnbella's picture
    qnbella
    35

    Just let go of your friend, telling her would hurt her no matter what. That's my situation w/ex-bff. Her 15 years ago ex start dating me two years ago.... that's when we stop talking forever.

    45 weeks 6 days ago Report Comment
  • bastille_75's picture
    bastille_75
    36

    Advah and jennifer76 are correct!!! To Advah - I would add #3 after you break you do not get the consolation prize of complete dominion over them and who they can and cannot date for the rest of their lives!!!!

    Also, to attempt to answer the question - you have to decide how much this friendship means to you. Do you wan to start to repair things with her - if so, you tell her now and even if she is initially mad bitter, etc., the friendship - if meant to recover - will. OR are you ready to accept the friendship as being over - b/c when she hears about this from anyone else including the guy - she will have what she'll perceive as the perfect excuse to write you off as a friend forever- rational or not. Good luck!!!

    45 weeks 5 days ago Report Comment

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