Dating Long-Distance, Going Nowhere

Dear Dr. Chani,

I have been dating a guy, let’s call him Yoni, for about two months. We live across the country from each other so we knew before we started dating that we would not see each other that frequently. At this point, we have had four dates in person. It could be that if Yoni lived close by, we would have had an easier time seeing each other and our relationship would have developed further by now. Since we have to date long-distance, I am not sure if it is possible to make this work.

One of the issues that I notice is that I am not much of a “phone person.” Even with my friends, I would rather hang out with people in-person than talk with them on the phone. I have a hard time finding topics to talk about and I dread the awkward silences. It is usually easier for me to carry on a conversation when I am doing an activity in-person since the activity gives us something to talk about.

Each time that there were over two weeks since our last in-person date, I hoped that seeing Yoni in person would supercharge my feelings for him. Unfortunately, when we actually met, I did not feel so excited to see him. It kept feeling like we were going on a first date, even though we had been dating for weeks.

Another aspect that makes this long-distance relationship challenging is that our dates are relatively long (around 8 hours!) I understand that it is a huge investment for him to fly in to see me and we should make the most of the time we can be together in person. But after about two hours, I get so exhausted that I just want to go home and crawl into bed.

Is it worth it for me to continue dating Yoni? If so, what can I do to make this easier?



Dear Ariella,

I can understand why you are finding dating long-distance to be very challenging. It sounds like the process of dating is being stretched out like a long taffy. Your in-person dates are spread apart over time. You also find the marathon-length dates to be overwhelming and exhausting. Then, when you speak over the phone between dates, you find it difficult to carry on a conversation. You seem to keep going through the motions of dating without really getting anywhere.

When you think about the experiences you have with long-distance dating, it is worthwhile to separate your issues into two main areas of concern. The first is that there can be significant hurdles involved with long-distance dating. The second is that developing a relationship can be elusive under any dating circumstances. Let us focus on each one separately.

Long-distance dating is different from dating in the same locale because in-person dates can feel like they have even higher stakes. Since you and Yoni know that it is not easy to meet, you try to accomplish more in the infrequent opportunities you have to date. When you have high expectations to develop a feeling of connection on your in-person dates, it puts you under pressure. Ironically, this makes it harder for you to connect. Pressure and connection usually do not mix. It also adds to your disappointment when your relationship does not progress as you had hoped.

There are practical ways to reduce the pressure of relying on in-person meetings to be your “all-or-nothing” chance to create your relationship. One important way is to take advantage of your phone or video calls to do more than just chit-chat. Don’t just call each other casually and unexpectedly. Schedule times to speak or meet virtually just as you would plan regular dates. Take the times you connect just as seriously as you would take your in-person dates. When you date virtually, give Yoni your full attention.

Since you find that you do not usually enjoy speaking on the phone, you may find it easier to lighten the mood and make conversation if you do an activity. Any game can be good to play together. In particular, you might find it helpful to play a game where you take turns asking thought-provoking questions. In addition, you can use video and bring souvenirs or pictures for “show and tell.” This is a great way to jumpstart conversations about topics that matter to you. Furthermore, you can share your interests by using concrete items to demonstrate what you like. Consider discussing and trading samples in music, writing, Torah, sports, etc. with each other. To take it a step further, try to take an interest in each other’s interests and use that to prepare for the next date. For example, if you know Yoni is interested in a specific topic, look into it a bit between dates. The next time you meet, you can talk about it and ask questions. Aside from helping create conversation, this shows you care and can help build your connection.

When you create opportunities to enjoy each other’s company and get to know each other when you are apart, it is less likely that you will feel like you are starting over again each time you meet in person.  It will help you to feel more familiar and comfortable.

Yet, there is another aspect to consider when evaluating your relationship with Yoni. Whether you speak to Yoni across the table or across the Atlantic, developing a relationship can be challenging under any circumstances. One of the essential aspects of feeling connected is to have the right types of conversations. Sometimes people imagine that when you are with the “right person,” the conversation will naturally flow. Yet this is not always true. Even when a couple gets along well, it can be difficult to come up with new topics to talk about and even harder to develop a deep and meaningful conversation. 

It is common for people to make small talk for a large part of their dating life. Small talk is like an appetizer, but not the main course. If you trade jokes, share cute stories, and briefly discuss world affairs, you will not feel connected. It is like leaving a meal before the entree is served. You do not feel satisfied. You mentioned that you prefer to hang out with people while doing an activity and you dread awkward silences. Is it possible that what is lacking between you and Yoni is not related to the long-distance, but to the quality of your conversations, no matter where you are?

Think about your conversations. When you discuss your past and present experiences, do you describe superficial details or are you willing to gradually let Yoni know your deep thoughts, feelings, and reactions? Is Yoni willing to do the same? When you share your genuine feelings about something with one another, it creates a meaningful conversation that can be energizing, authentic, and seldom boring.

As you create more opportunities for you and Yoni to really get to know each other in an enjoyable way, you might find that the long-distance is less of a challenge. Hopefully, you will also get to know each other on a deeper level, which can help you to develop your relationship and gain clarity about your future.

Wishing you much success,


2 thoughts on “Dating Long-Distance, Going Nowhere”

  1. I sometimes take notes b4 a conversation so I can cover things I want to say.
    My 2nd husband was living in Passaic and I was living in Cleveland when we were set up. We phone dated and emailed for awhile as I was making my son’s bar mitzva. We then took turns flying out every few weeks. I like having a relationship before meeting as you get to develop a relationship without externals, but I can see how it’s not for everyone.

    1. You make a great point about one of the benefits of a long-distance relationship! Thanks for sharing your positive experience!

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