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He Said, She Said: Dating Your Best Friend’s Ex

Have you ever dated your best friend’s ex? There are no actual rules when dating someone, but there is that one unwritten rule that can often lead to an ugly love triangle or an altercation with your best friend.

Image Credit: Shutterstock

Image Credit: Shutterstock

Romantics might say ‘love sees no boundaries’ but often times in reality there are, especially in cases of dating a best friend’s ex. If there was a black and white answer, it would be that you don’t date the ex. It can damage a friendship and hurt those involved greatly, yet if done with honesty, clear communication, respect and understanding, you can get over that hurdle and pursue that someone who just might be perfect for you. After all, love is anything but simple.

The dating department is a complicated one and all these unwritten rules of dating an ex can sometimes get overwhelming when all you really follow is your heart. There are key factors to consider when pursuing an ex. For one, it’s vital to communicate with your best friend about your interests in the ex. This is essential in sustaining your friendship by keeping continuous trust and honesty between you two. With communicating, you’re considering their feelings and making sure nothing is too awkward between the both of you. Think about how weird it would be had your best friend and the ex dated for ten years and you then moved in? The stronger the years of commitment between them, it’s guaranteed they were heavily invested with one another. Secondly, you want to make sure the individual you’re pursuing is really worth the risk. Put yourself in your friend’s position and examine the situation. If you truly believe the ex is the one for you, explain to your best friend how you feel because true friends always put your happiness before their own.

This week we hear from John of Sacramento, California who has been dating his best friend’s ex-girlfriend for five months and the couple are now getting tired of sneaking around. John is unsure of how to tell his best friend and our writers help him out.

He Said She Said - John May 15 2013

Drew says…

John, I feel your pain. I’ve been on both sides of this before; and it can be really difficult (and can break up a friendship). I think you just need to sit him down and be straight with him. If I’m honest, I can’t imagine he’s going to be happy that you kept it secret for this long without telling him (maybe you try to gloss over that bit a little); but if you don’t tell him the truth, he’s going to find out, and then he won’t forgive you.

When my best friend started dating my ex without telling me, I wasn’t bothered that he was dating her, but I was pretty pissed that he didn’t tell me; so I think that might be your bigger problem to deal with. There’s not really much other advice I can give. Either he’ll forgive you, and your friendship will get through it, or he won’t.

I don’t think there’s much point in you breaking it off with your girlfriend for him. As much as the whole “bros before hos” thing is a great concept, you’ve been dating for a while now; if you break it off, you’ll end up resenting him for making you do it I would guess.

Best of luck John, tell us how you get on.

Rebecca says…

John, I understand. I had two best friends in high school that were dating. Eventually they broke up but I stayed friends with both of them. In fact, I started talking to the guy. I was in the same position (almost) as you are in now; however it didn’t work out for us because it was too awkward. My advice is similar to Drew’s, just be honest with your best friend. It is doing no one any good hiding the truth. That way both you and your girlfriend can be open about and enjoy your relationship without having to tip toe around.

Your friend, if he is your true friend, will eventually forgive you. Even if he is angry for awhile, if you’re meant to be friends you two will make up. It is an awkward situation to be in, but there is no way around the truth. Hiding it is only making it more complicated and worse than actually telling the truth.

Kelly says…

John, I definitely think you are doing the right thing by thinking about the situation critically, and knowing that something needs to be done soon. I agree with Rebecca and Drew, but also have a few things that I think you should consider.

First of all, it definitely is not a great thing that you have been dating your girlfriend for 5 months now and have not told your best friend yet. This is your main issue, so I would focus most on this. If this ever happens again, remember that honesty, in the beginning, is the best strategy for dealing with any problems or drama in life. The fact that you have waited 5 months now makes your honesty not as relieving or effective in helping to diffuse the situation. He is going to feel like you went behind your back, have been sneaking around (which you already admitted you have done), and that you are not a “true best friend.”

What you need to do, is to think critically about why you did not tell him in the beginning, and why this situation is different perhaps than a similar one- say, one where you date your best friend’s ex-girlfriend too soon after they break up and he is still in love with her, or you are the person who your best friend ex-girlfriend is cheating on him with. The reason that this is different is that some time has passed since your best friend’s relationship with her so it should be well over with, and that you knew the ex-girlfriend (your current girlfriend) first, and had a friendship there that was healthy and in fact always had some potential.

All that being said, I think you need to sit down with your best friend and with your girlfriend and explain everything from top to bottom, including why you didn’t tell him in the beginning, which hopefully is because you were afraid of hurting him and just didn’t know how. It should NOT be because you thought it was wrong and felt guilty. Do not act guilty, instead make sure he knows how much you care about him, but that your feelings for his ex (your current girlfriend) are more than just a fling, and that you care about her and him a lot. Make this clear and I think you have a shot at being able to hold on to both things that I know you value!

Andrew says…

Hi John, admittedly this is a very complicated situation, but I think Kelly and Rebecca gave you some great advice. You said it best yourself when you said that this girl isn’t the kind you want to hide, so the only real solution left is to tell your best friend. If you tell him in and open and honest way and, like Kelly said, make it clear that you were afraid of hurting him more than anything, then you two can begin figuring out what it means for your friendship.

He may not accept it right away, but you should be prepared for that. Give him time to process it and think about what it means for your relationship with him. Try to see his side (i.e. that he’ll have to hear you talking about her and perhaps will get together with you and her at times) and that those things might not be easy for him. If you two can talk about the implications open and honestly, he should respect you and your relationship with her more.

Kelly also pointed out the reality of the situation, which is that your honest comes a little late in the game so it feels less genuine. Like Kelly said, make it clear that you wanted to establish the relationship with this girl first, make sure it was something you really wanted, then figure out how to tell your friend without hurting his feelings. I hope all goes well with you, I know this is not an easy situation, but if he is a true friend to you, he will eventually want to work things out when you’re honest with him.

If you seek advice from our writers, email us at thehudsuckerblog@gmail.com! Perhaps your question will be featured in our next installment.

While our team of writers have given their advice with the best of intentions, they nor anyone of this site assume responsibility for your actions or the results of them.
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