Should you date an ex’s friend? Should you date a friend’s ex? Should you date someone you know your friend was once interested in, but never dated? As if dating wasn’t complicated enough (especially if you live in a city or region where everyone knows everyone), there are so many stipulations on the moral front when it comes to right and wrong in the dating scene. But does it have to be that way?

Most of us have found ourselves in some sort of sticky potentially romantic situation at one time or another, forcing us to choose between what we feel is the right thing to do, versus taking a chance on what could be a great new relationship. This can be viewed two ways:

1.)  Most relationships don’t end in marriage, so it’s really not worth going down that road to potentially ruin a good friendship.

2.)  The relationship did not work out with your friend and their ex for a reason, so why not ask your friend for their blessing and see if you two are a better fit?

I believe in the latter. I have seen a few guys get bent out of shape when one of their buddies decides to hang out with someone they used to date. When this happens, they often weren’t even in a serious relationship with the woman, but got mad at the friend anyway, saying the friend broke “the guy code.” They also get mad at the woman they once dated for accepting the offer from the friend to get together. From a personal perspective, I’ve been the woman in this situation. A friend of an ex I briefly dated asked me to get together; I wondered if he knew I dated his friend. He must have known; they were such close friends! Still, it’s easy to find yourself in these situations in NYC as people date a lot and don’t necessarily talk about every date they go on if it’s not that serious. And if you’re attracted to a certain personality type, there’s a good chance you could find yourself attracted to the company your guy keeps.

In a world where it can be so difficult to find “The One,” I don’t think there should be any rules when it comes to love. If a relationship didn’t work out between you and someone else, and you know your friend is interested, I don’t see the point in getting angry at your friend for seeing something in your ex that you may not have seen. As long as he or she wasn’t strategizing a way to break up the relationship while you were dating, wouldn’t you want your friend to find happiness? Even if it’s extremely upsetting that they may have found happiness in your ex, I would say it just wasn’t meant to be for you two. The bright side? You could have been a catalyst in helping them find their b’sheret!

If someone asks you to go out and you know they are good friends with someone you may have dated, or with whom you’ve been intimate, go for it anyway. Just consider whether or not you should ask the new person if they know you dated their close friend. My advice? Just get to know each other and take things slowly until you find out their true intentions. If their intentions are of a casual nature, you may not want to move forward, considering the close connection. However, if the relationship has the potential for more, you can always talk about it down the line. However, if you had anything significant with the ex, and they are good friends, that new person likely already knows. If the ex never spoke about you, then there couldn’t have been much there for him to get mad about. So regardless, when it comes to love, take chances, because like Leo Buscaglia said, “Love is life. And it you miss love, you miss life.”

Based in NYC, Michelle Jerson is a radio talk show host, relationship coach, and founder/CEO of the travel site  On the side, she recruits for an international matchmaking service, and is currently seeking a few good men to join for free!  You can also spot her on NY1 News telling you how to get around on the rails and roads! Contact Michelle at


  1. Michelle,

    I enjoy reading your J-date columns, but find myself thinking I have a different view on the topic, maybe because I’m a guy. I think it would be interesting to your readers to have like a “point – counterpoint” format where you write about a topic from a woman’s perspective and then you get a guy to write about it from the man’s perspective; not that the two articles always have to be opposite, but it would be interesting to compare and contrast the two viewpoints.


  2. Hi Michelle,

    In my opinion, dating a guy friend’s x is bad business in general. BTW, “Bro Code” is the official term. Just think about your own x boyfriends and imagine continuing a friendship with a close girlfriend simultaneously as she becomes intimately involved with your friend – hears all about your private information, how you are in the bedroom the things that he hated about you. Do you really think you’d have no feelings on the subject if you were on the other end? You’d have to be heartless to have no feelings.

    As a guy, If you want to bust the “Bro Code”, it is best to ask your guy friend for a sincere permission of your desires to court his former girlfriend or you will unquestionably loose your friend. Remember, this should be done BEFORE you even ask her out. Minus this Mensch-style approach, It makes a guy question if you were ever “friends” or was he lurking around to spy on your relationship – waiting for that moment.

    From personal experience, I’ve had a friend, (no longer), call me after he was dating my x for about 6 months in secrecy. He felt entitled and he believed he owed me no explanation since he patiently waited 6 months to reach out to her. Granted there’s not Federal Law on dating another person’s former lover. Friendships and romantic relationship whether with a man or woman are based on honesty and respect.

    Dating someone’s ex without asking for “permission” is a great way to ruin a friendship. Simply moving forward and dating someone’s former girlfriend is self-centered behavior and fails to acknowledge that you give a crap about your guy friend’s feelings. You’re just worried about yourself and finding someone. With that attitude, I believe you are bound to fail since you would have a fundamental flaw in your character.

    But, if you are upfront and ask your guyfriends – who knows, perhaps he won’t care. I once set-up a guy friends with an x, but I was the initiator of the idea. But if he does find it upsetting or obtrusive, as a guy, you will need to make the decision as to whether or not you have any interest in tossing a valued male friend to the curb for the chance at his former woman. Statistically, dissing your guy friend is just bad character. Chances are, your relationship won’t work out anyhow with his former girlfriend – is it really worth tossing your friendships for a shot in the dark? There are plenty of women – especially slightly older (35-40) who are great wife candidates – who screw over my friend?

    I value my friends too much to approach this area without open and honest communication since my friendships and girlfriends mean a great deal. The “Bro Code” helps guys know which one of your friends will hover by your side, only to hop on your girlfriend at the first signs of turmoil, and will take advantage of your friendship by using personal discussion you might have shared in confidence. I think it’s pathetic for a man to behave in this way.

    There are many who might argue that engaging in dating your friend’s former girlfriends is a sign of aggression – as they capitalize on the “insider information” you may have provided throughout your friendship. It’s like being a double agent.

    The only example when busting the “bro code” is actually helpful is when “Oh, she and I had a first date…and we’re not a match”…in this case, nothing emotional is invested. Who knows, maybe I can help a friend – otherwise, that’s the official protocol.

    And to the remark of what if my x girlfriend could be your wife? Ask you male friend for his blessing. Although it’s a tough conversation, if you can’t man up, and ask in you guy friend in advance, you are a crappy friend.

    Open communication and respect will go a long way – especially if you ask you guy friend along the lines of this “Hey …I wanted to talk to you, but I’m concerned that my question could compromise our friendship – something I REALLY VALUE. I want you to know that I’m interested in her – not for a quickie, but I really think she and I could possibly be great together. I would really love it if you were cool with this. Who knows, she might say NO, but there are a lot of reasons who I’d live to approach her. Make sure you tell your guy friend – especially if he’s uneasy and this doesn’t go well, that he can take his time to think about it and if he’s really uncomfortable, you won’t hold it against him – after all there are how many Jewish girls in NYC?

    In closing, many people dismiss these steps because they so badly want a partner – but if you can’t respect your same-sex friends, chances are you won’t respect your partner either.

    Making a relationship work is tough enough, but what if your best friend had history–messy history–with your new boyfriend or girlfriend? Could you handle the bad blood between the two most important people in your life? Do you have to deal with your friend’s unresolved feelings, or worse, your current boyfriend’s? Do you feel like you’re being forced to choose either a new love or an old pal? Or are you constantly worrying that something is still going on between people who claim their past is behind them?
    If you’re stuck between your love and your friendship, MTV wants to hear from you! If you appear between the ages of 16 and 30, submit your story, complete with contact info and a picture to:

  4. Need to share this with the folks at Several would benefit from reading it.

  5. I disagree to a point. I dated a man about ten years ago, I have since moved on and I am married. I just think he is absolutely bad news. This is not just as a result of him being an ex. He dated me for almost two years, and we were engaged for three months. He lost his job while we were living together, and cheated on me with my best friend. She was sick and single, so she tagged a long on a lot of our outings together. They started dating a month before him and I broke up(I didn’t know at the time even though I had intuitions and signs). I found out they were dating when I caught them in bed together, and a mutual friend told me they were together. This relationship caused an apartment lease to be broken along with trust issues. I was so angry, after a brutal confrontation with the two of them we stopped being friends. It was about three years later that I forgave her(not him). We had a long history, and even though she went about it the wrong way, I knew she was in love. They were together for almost 8 years, he never proposed to her. She was very sick and continued to get sicker. He broke up with her while she was in the hospital over a text. Remember that mutual friend that told me about my other friend and my ex’s indescretion? Yes, he was cheating with her through sexting. He wanted to be with her. My friend who stole my ex was now having him stolen from her. Her fears were realized when she caught them having sex. So….what do you think if they are a serial friend dater? They constantly cheat on their girls with their friends? My sick friend passed away two years ago….the heartache was too much.

  6. Im dating this man I know from home I dated his cousen for 2 months then after 3 year the lady broken up wth his boyfriend we meet he had a crush long ago bt was respecting his wife,iwas not into him at all but after we meet n start proposing,talking,loughing,luv develops and now we are dating he want our relationship to be out so people will know im scared of her fimaly coz they are so we do love each ather so far.wat do I do?

  7. I totally agree with Bald! The exact same thing that happened to him is close to what happened to me. I accepted that my ex broke up with me and that u wasn’t the one for him. But I very much that I was betrayed by my own close friend. I find it disrespectful, disgusting, and that she had no respect for our friendship at all. It is very disrespectful to date ur friend’s without their permission.

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