Ask Aysha: “Is It Okay to Date My Best Friend’s Ex-Boyfriend?”

    My best friend and her ex-boyfriend broke up several months ago. When I asked my friend if she’d mind if I dated him, she initially said it’d be okay. Now, she’s saying that it would bother her if we started dating. But I like him a lot. What should I do? Should I date him or not?

    This is a very complex situation that could put a strain on even the strongest of friendships. Ultimately, the decision is yours, but here are a few things to consider while contemplating the best way to handle the situation:

    • Have you sought God’s guidance? As a Christian, God should be at the center of every decision you make, no matter how small or big. It’s very important that you ask The Holy Spirit to guide you in the right direction as you try to figure out the best approach to take.
    • Don’t make decisions solely based on emotions. Although emotions do serve a purpose (or else God wouldn’t have given them to us), don’t base your decision solely on emotions. Even though you like this boy a lot, make sure if you decide to date him that it’s the best decision for everyone involved.
    • Ask yourself why you want to date him. I’m a firm believer that Christians should be courting and not dating. The world dates to have fun; however, Christians should begin courting when they’re ready to build a life with their spouse. Do you want to establish a relationship with this boy because God has revealed to you that this is a relationship you should be in? Or do you want to date him because he’s kind of cute and you think it might be fun? Then ask yourself if this potential boyfriend is worth jeopardizing your relationship with your best friend.
    • Can you just be friends with him? Have you considered why you like this boy so much? Is it because he’s funny, or kind? Or maybe it’s because he’s generous or smart? Whatever the reason that you like him, could you be able to enjoy that part of him while just being friends?
    • Have you been honest with your best friend? Have you told your friend that you’re attracted to her ex-boyfriend, or have you just been asking her hypothetical questions about it? Whether or not you decide to date her ex, it’s important to talk to your friend about it first. Be honest about how you’re feeling, and let her know what your intentions are regarding the situation. Although she may not like it if you do decide to date him, she’ll respect your honesty.

    I’m not saying that you should or shouldn’t date your crush because, ultimately, only you can decide that. However, I do implore you to seek God’s voice and guidance as you make your decision so that no one gets hurt in the process. Be sure to pray about it, and however you decide to approach the situation, make sure that it’s done in love: Love for God, love for your friends and love for yourself.

    What do you girls think? Would you date your best friend’s ex if you liked him a lot?

    More Stories Like This on Project Inspired:

    Ask Aysha: “Are There Any Good Guys Left?”
    Ask Aysha: “Help! My Friends Keep Pressuring Me to Ask a Guy Out!”
    Ask Aysha: How Do You Know If the Love Will Last?”

    Aysha Ives
    Aysha Ives loves God with her whole heart and has a desire to help hurting people. With a Masters Degree in Psychology, she combines her education and experience with her love for God to help people live whole and fulfilled lives. Aysha is an Author, Mental Health Provider, Youth Church Teacher, and the mother of one gifted little boy whom she absolutely adores. Aysha is honored to be able to share her love of God with Project Inspired readers. Aysha is also the author of God Cares About Your Stuff: How To Believe For Tomorrow When Things Look Utterly, Completely, And Totally Impossible Today, released February 2013- Available at Amazon.


    1. first of all you are not suppose to go out with ur best friend becuz it will lead to bad friendship it saw happen to alot of people and i dont want it to happen to you cause i love you like a sister and i dont want you to be sad that ur friend is mad at you becuz of her ex so if u dont like my advice thats ok so talk soon bye

      • I actually did go out with my best friend last year. We dated for about 4 months before we broke up because we realized that this wasn’t working. We are still really good friends now. He is currently dating one of my best friends and they are going strong at 6 months, and I think they will last the distance. They both came to ask me how I felt about them dating and I told them I was fine with it because of two reasons. I no longer had any claim on who he wanted to date and so I had to right to say no just because he was an ex. Also, having known them both a while, I could tell that they complimented each other, and they wouldn’t have considered dating unless they thought that it would have led to marraige.

        I have a problem with people saying that they shouldn’t date a friends ex just because the friend says no. If the friend still has feelings for the ex thats one thing, but any other reason shouldnt be valid. The only reason you should “date” a guy is in the intention of maybe getting married in the future. A person’s past relationships should have no bearing.

    2. About two years ago, my bestie dated this amazing guy. He had/has fluffy, blond hair, has a hilarious sense of humor, and is a Christian. And although we all knew he wasnt perfect, he was as close to it as he could be, in our eyes. Anyways, my friend and the guy dated and had a good relationship. They texted 24/7, kissed, hung out at school. So you can imagine it left a lot of emotional damage when he dumped her. After that, knowing what kind of hurt he had caused, one of my other friends dated the guy. My bestie was hurt even worse! I felt bad for her, and consoled her, but I felt bad because I had wanted to date him too! Well, everything got smoothed out (sorta) and this advice has helped me a lot. Thanks again!

    3. People get all mad because of the “girl code” where you are apparently not supposed to date anyone that your friend has. But there are so many pointless relationships in middle school, I’m sure that a 5 hour relationship doesn’t count.

      My advice to anyone with this problem is– If your best friend has JUST been dumped or broken up with, dont date the guy. If you really like him you should probably wait until your friend has gotten over him and gave you permission. If she’s a girl that dates a ton of guys… It probably won’t be as hard for her to see him date you.

      Well thats my advice, I haven’t been in this situation before but… 😀

    4. I think that if you break up with your boy/girlfriend, what that means is that you’re okay with them dating someone else. I think obviously there should be a “buffer zone” – a time period for them to get over it, though.

    5. I am actually in this situation right now. It is definitely putting a slot of stress on my friendship with him and my best friend. It’s not easy because she and I both want each other to be happy and she recently just told me she still has feelings for him. We talk about it often and we can talk about it with out arguing which is such a blessing. We both agree that time will tell and that none of us are at the point in our lives where dating is practical. We pray about it together often and try to be unselfish about the situation. If something is going on that she doesn’t like she will tell me and visa versa. Although it isn’t easy sometimes, our friendship is amazing.

    6. So right now, I’m going out with my ex-bestfriend’s ex. But before you judge, hear me out. One day, in went to a school football game with my cousin, and we sat alone on the stands. But then I look back and I see my “best friend”‘s ex. He was a friend of mine from the start so I took my cousin to meet him and his little sister, whom was there with him. For the next few hours, I told him everything that was going on with my “best friend”, since she was ignoring me and my problems and was too caught up making out with her boyfriend all day long… Anyway, after I went home, I realized that I kind of like this guy, and he really knows how to deal with all sorts of situations. Jump forward a week or so, and my supposed best friend is talking to me, asking me if I’d go out with her ex. Next thing I know, he’s asking me to be his girlfriend. I was shocked at first, but apparently, my now boyfriend and ex best friend had planned out the perfect moment for him to ask me out, and my ex best friend said she didn’t care who I did and did not date. Fast forward 3 months, and my best friend of the time comes and tells me that it bothers her seeing me so happy with him, and that she hates seeing that I make him happier than she ever did. Then she finds my boyfriend and yells at him (in front of me and HER boyfriend) that he was the worst bf EVER! We were all in shock, and I told her then and there, “You could’ve told me from the start that this is how you felt, but now it would actually hurt me to lose him.” After that, her and I drifted apart, and I’ve been with my boyfriend for 6 months, and in that time, he has come to know God. 🙂

    7. My view on these types of issues is that if it didn’t work out between your best friend and her ex, why shouldn’t it work out between you and the boy? The only reason a friend would tell you not to date their ex is if they still weren’t over the boy. If you don’t go out with him, everyone will be unhappy: you and the boy won’t be in a relationship and your friend is still unhappy because she’s not over him.
      If this person is really your best friend, they’ll realize that you should be allowed to be happy along with her ex. Why make three people unhappy with the situation?

    8. One of my friends started dating my Ex and we aren’t friends anymore. It’s not that I’m jealous or anything, she just never talked to me about it. Her and my ex were good friends before and when he asked her out she said yes but it really hurt. Mainly because I told him that I didn’t want a relationship now but I was willing to wait until after high school. Obviously he didn’t want to so that’s his loss. But she just went ahead and said yes. I’m still pretty upset with this… She should have known I would be mad or asked how I would feel.

    9. I’m in the same situtation i have fallen for my best friends ex, and in my opinon it should be okay since it didn’t work out for them why can’t it work for you guys. ands if they are a true friend they should be happy for you and support you.

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