March 4, 2024
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March 4, 2024
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Dating Two People: How Do I Choose?

By Dr. Chani Maybruch

Dear Dr. Chani,

When I began dating a few years ago, I quickly realized that in my hometown in the midwestern United States the pool of people for me to date is quite small. I began traveling to the NY/NJ area on weekends so that I could expand my options. Yet, after many hopeful — yet unsuccessful — trips, I agreed to meet two people on the same weekend. This is how I came to be dating two guys for approximately a month. I never planned to continue this way for so long but I actually was surprised that I liked both of them. Now I am not sure how to decide between them.

There are a lot of similarities between the two guys that I am dating. I have an easy time making conversation with both of them since they both have a wide range of knowledge and interests. I am really impressed with their friendliness, intelligence and sense of humor. They are both learning full-time and plan to go into a career as a rabbi or a teacher.

If I was dating either one on his own, chances are that I would continue dating him long enough to figure out if I wanted to marry him. But, since I am dating both of them, I do not have the luxury to wait around and see. I feel pressure to make a decision about who to continue dating.

I thought about what would happen if I continued to date both of them. Yet, I worry about what would happen if either one of them found out that he was not the only one I am dating. My friend told me about what happened to her when she dated two people. One of the guys passed her while she was on a date with the other guy, and he made a very sour face. She ended up having to explain to each person that she was dating both of them at the same time. In the end, both of them broke up with her.

Is there a way I can continue to date both of them? If not, how should I choose who to date?


Dear Chaya,

It is not easy to live in a remote location and have to fly in to date in the metropolitan area. It is understandable that you chose to date two people, especially with your previous history of unsuccessful attempts at dating. Now that you have “too much of a good thing,” you are faced with the opposite challenge: narrowing down your options. What can you do to make this easier?

As you suggest, it does not seem best to keep dating both people. Although it is theoretically possible, it is unlikely that it will work to continue dating both guys indefinitely. It is also not respectful and fair to keep it a secret as you date two people. Try to put yourself into their shoes.

What would you feel if a guy was dating you and another woman for a while? If you found out, you would likely feel somewhat jealous and insecure about his splitting his time between you and another woman.

Furthermore, it is not beneficial to you as you develop a relationship with either person to have the added stress of juggling another relationship, especially when it is a secret. While the stress of the other relationship is on your mind, it can be hard to be yourself with either of them. That means that although you might try to develop relationships with both, there will also be something impeding your ability to fully develop either relationship. Therefore, at this point, it makes sense to choose.

Once you come to terms with the need to select one of the people, it might seem overwhelming. How can you choose between two people that you like? One strategy is to introspect and reflect on the qualities you would like in a spouse. Go back to the basics of what is important to you.

Brainstorm and compose a list of the qualities you know you need and want in a spouse. Try to keep your brainstorming theoretical, without focusing on either of the people you are currently dating. Then, evaluate the extent to which each guy you are dating has those qualities. You will probably find that one person is a closer match and it makes sense to choose to continue dating him. Try not to second guess your decision as you move forward with that one person. Keep in mind that you can only make a decision based on what you know now and do not doubt yourself.

Part of making the decision is breaking up with the other guy, even though it can be difficult. That usually includes sharing why you do not want to continue. If you cannot think of a specific reason, a truthful explanation you can offer is, “I’m not ready to move forward and I need to date other people to get more clarity.” This reason leaves a door open for you if you end up wanting to resume dating him.

After you select the guy that you feel you would most like to date, you might want to share with him that you had previously dated a person at the same time as him. One reason to let him know is if you feel stressed about keeping it a secret. It is stressful to keep any secret from someone you are dating, even if it is private information about you or your family. In a case like this, the stress might be even more intense since the secret is directly related to how you have been dating. Holding back information that you are worried about often creates a feeling of emotional distance that interferes with the very connection you are trying to create when dating. Therefore, it might benefit your relationship and increase your trust to let him know what has been going on.

You are the best judge of the situation. Once you break up with the other person, ask yourself if your history of dating two people remains on your mind. If you honestly feel that you forgot about it, it might not be necessary to share it with the person you continue dating. On the other hand, if it stays in your memory, there are chances that it will be casting a shadow on your ongoing dating experience. If so, consider sharing that you had previously been dating two people and your reasons for doing so.

As you navigate your dating experience, it is natural to desire complete clarity and decisiveness. This situation will probably challenge your ability to be completely certain about your choice. Allow yourself to be human, make the best decision you can, and let honesty be an important part of your relationship.

Wishing you much success,


Dr. 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 and teaches online courses to help people create their ideal relationships. Get free relationship resources and contact her at

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