man looking at bridge

Why Do My Dates Always Dead End?

Dear Dr. Chani,

I recently went to a dating coach to help me figure out where I am going wrong with dating. The advice I received does not seem right to me and has not helped me so far. I hope you can guide me to understand what I am missing.

My issue is that I have been dating for several years, but I can never get past the first few dates. It is pretty surprising to me that I have not been able to get to the level of a serious relationship with anyone that I have dated. My friends and family seem to think that I am a great catch. They are always setting me up. I am twenty-eight years old, work as an actuary, and I have been told that I am good-looking.

Whenever I go out, things fizzle out after just a few dates. Sometimes I say no, and sometimes the other person says no. But I feel that it is the same thing all the time – there is nothing to talk about. After a few dates, we start having awkward silences and there is very little positive energy.

I went to a dating coach to discuss this and he told me that I am searching for the wrong thing. I am focusing too much on the conversation. He told me not to worry if my conversations do not seem to flow naturally. It might simply be because of my personality. He explained to me that when you are married, there are a lot of things that come up in day-to-day interactions, so those provide things to talk about. Dating is artificial, so you feel a need to keep on coming up with things to discuss. He assured me that it will not affect me in the long run. Instead, I should focus on finding a person who is nice, with fine character traits, who I find attractive, and see as a potential marriage partner. He advised that as long as we do not have tension, we should continue, even if we do not really have enjoyable conversations. He also suggested doing activity dates and bringing games on dates so that the quiet is not so noticeable.

I have tried his advice, and I feel so nauseous about it that after a few dates, I cannot continue. At this point, I am feeling completely hopeless. What do you advise?

Thanks for your help,


Dear Evan,

It is understandably frustrating for you to invest in so many years of dating, putting in solid effort and energy, with no success. You even consulted a counselor whose advice did not sit well with you. It sounds like you feel you are hitting a brick wall.

Conversation is probably the most important way you connect with others. If there is poor conversation, whether on a date or in another social situation, you will likely feel that you have little connection with the other person. If, on the other hand, your conversation is rich and meaningful, the people in the conversation will probably feel more connected to one another. Since conversation is so important, let’s examine some things that differentiate poor conversation from rich conversation.

Firstly, conversations go well when you are interested in what the other person is talking about. Your date can probably sense if you are focused on what she is saying. Take a genuine interest in what she shares.  That does not mean that you need to have your own general interest in the topic; it is enough for you to be interested just within the context of that conversation.

Showing interest in what your date is saying shows that you are interested in her. What your date is sharing is more than just an idea, it is a window into her life. It can allow you to get to know her. While you are on the date, try to get to know her as much as you can, even though you might not marry her. She will feel more connected to you when she senses that you care about what she has to say. It might also guide your conversation to areas that are deeper and more meaningful. 

Secondly, we really connect with someone else when we have conversations that focus on our feelings, rather than just facts. Emotions are our way of experiencing life and interacting with the world. Emotions flow from the core of our being. So when we share our feelings about something, we allow someone to understand us. Similarly, if you ask your date about her feelings about something, you can connect more with her. 

In the early stage of a typical dating relationship, most conversations begin with facts. You discuss questions such as, “What is your job?,” “How many people are in your family?,” and “What do you do for fun?” While these are essential springboards for conversation, if the conversation remains at the level of facts, it will usually reach a dead-end at some point. Also, many people find conversations that focus on facts to be somewhat dry and boring.

A great way to develop a conversation is to reach for the feelings. This is true when you listen to someone else and when you respond to a question that is posed to you. For example, if you ask your date, “What do you do for fun?,” and she says, “I love to jog,” you might ask a follow-up question such as, “What do you like most about jogging?” Similarly, if you are asked, “What is your job?” – you can share more than just the facts. You can describe what you like about being an actuary, what you find challenging about it, and why you chose to be an actuary. The more you share your feelings about the topics you discuss, the greater your connection will be. Try to encourage your date to discuss her feelings with you as well. The more you focus on feelings, the more connected you will feel, and there is a better chance that you will both consider it to have been a good date.

When you take a real interest in what your date is saying, and focus on reaching for the feelings, you will likely notice a positive difference in your conversations. Aside from making your dates more interesting and meaningful, having richer conversations will make it easier for you to get to know one another to the point that, eventually, you decide you would like to spend the rest of your lives together.

Wishing you much success,


2 thoughts on “Why Do My Dates Always Dead End?”

  1. I liked your advice to Evan. If you ask more feeling type questions or offer that in your conversation with taking an interest in the other person, you will at least feel more of a flow in the conversation.
    In addition, with the right person, who you are destined to be with, the conversation will work.
    Each conversation is great practice for the next and we get better at each attempt.

    1. Absolutely! One way to deepen a relationship is to “piggyback” on a previous conversation. You can mention, “Remember when we spoke about “x”? I was wondering …” It shows that you remember your conversations, are thinking about them, and take a genuine interest in your partner. Revising conversations in this way can take your relationship to a whole new level!

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