Dear Dr. Chani,

What is your opinion about going out with a close friend of someone you went out with for a while? Someone called me to ask if I would date a guy who is in the same circle of friends as a guy I went out with for three months. I am not sure what to do.

About a year ago, I dated a guy for three months. We were almost engaged, but I had some reservations. He had not yet started graduate school and had no immediate plan to earn a living. My family, particularly my father, was very against my continuing with him. Even though we enjoyed spending time together, I could not push myself to get engaged to him. Eventually we broke up.

Now, one of his close friends is asking to go out with me. I am not sure if it is fair to the first guy if I go out with his friend. He is probably going to be really upset and jealous that I am going out with his friend.

Also, if things work out with this new guy, I am not sure if I would feel comfortable seeing his friend (my former dating partner) at different social events. It might stir up old feelings and constantly remind me of our relationship. A part of me really wants to put that chapter of my life behind me.

Is it worthwhile to go out with this guy if it might be awkward and uncomfortable to see his friend?

Sincerely,

Chava

Dear Chava,

You are asking a lot of good questions. There are several things to consider in making this decision.

Firstly, ask yourself why you would want to go out with this friend. Is there something that draws you specifically to consider him? It is always helpful to think about why you are drawn to go out with a person. Yet here it is even more important. You might want to go out with him because you think he could be a good fit for you. On the other hand, part of you might be drawn to him for other reasons. Sometimes, if we are not allowed to have something, we try to find a way around it. If you had a connection to his friend and were not able to continue that connection, you might be drawn to this guy as a way of either connecting to or substituting for the original person you were dating. The former reason to date this person, because you know he has specific qualities that interest you, is a basis for developing a great relationship. If it might be for the latter reason, that he is replacing the original person, then it might not be best for you to date him.

How do you know which one is the stronger pull? If you can tell yourself why you want to date him, regardless of his association with the person you formerly dated, it can indicate that you are dating him for his intrinsic qualities.

Chances are that you will find specific qualities that draw you to date this person. That makes sense because you were clearly interested in the person you previously dated and there are often similarities between people who become friends. As the saying goes, “Birds of a feather flock together.” People within the same social circle usually have a lot in common. Of course, it is not always true. But it is probable that if you did see a lot of attractive qualities in the first person, that you might find similar ones in his friend. Try to become more aware of what those things are. Aside from the benefits you might get in terms of clarity in your own dating, it can help you determine if you have good reasons to date him or he is your mind’s replacement for his friend.

If you do determine that there are reasons to date this guy in his own right, then we have your second group of questions. How do you deal with the negative feelings that your former dating partner might have? Also, will it feel awkward to see your former date at social events?

It helps to differentiate between the short term and the long term here. If you do end up marrying this guy, in the short term, there might be mixtures of feelings and some awkwardness in crossing paths with his friend you dated. Yet over time, those feelings should gradually dissipate. As you move on in life and each of you develop independent and healthy relationships, the dating past becomes less relevant compared to the strength of the marital relationships that you form. Some awkwardness might remain for a while, but that pales in comparison to having the opportunity to date this guy and possibly develop a beautiful relationship.

Keep in mind that people often react to each other’s reactions. You can lead the experience of interacting with your former dating partner. He will likely take his cues from you. If you decide that you are going to behave in a normal, pleasant and appropriate way when your paths cross, he will probably act the same way. You can create the reality of normalcy and matter-of-fact interactions. If you take this approach, chances are that he will do the same.

What if that still does not work? What if the person you previously dated behaves in a standoffish, jealous manner? Recognize that you are doing something that is normal by going out with this second guy. It is not advisable to stifle yourself because of the adverse reactions that someone else might have. You have no way of knowing how he will react. Even if he finds himself upset or jealous for a while, he needs to address his feelings on his own or with people he confides in. It is not your job to make sure that he does not possibly feel this way. Another way to see it is that short-term jealousy and discomfort might be possible results, but they are not enough of a reason not to date this guy if it makes sense to you.

As you think about dating this person, you might discover specific aspects about him that make him a good potential marriage partner. If this is true, then go full-speed ahead and see how things pan out. Chances are that any negative emotions that might exist for you and/or your former dating partner can be avoided or controlled or will dissipate as time marches on. If you are right for each other, you will end up discovering a stronger bond than the initial discomfort that anyone in the situation might feel.

Wishing you much success,

Chani

Chani Maybruch is a social psychologist and relationship coach, specializing in teaching emotional-connection and communication skills for over two decades. She coaches individuals and couples, teaches courses on how to become a master of relationships, and provides free relationship resources at chanimaybruch.com. Learn a step-by-step method to improve your ability to emotionally connect with her online course: The RELATE Technique™—Seven Steps to Emotionally Connect Through Conversation. Reach out to her at [email protected].