Dating and Still Looking: Stuck

Dating and still looking

When I chat with singles in my office and they tell me about their dating experiences, sometimes it saddens me. Here are lovely individuals, putting themselves out there, receiving no follow up, or have short-term flings and too high expectations. I wonder, to others, what makes this person undateable? 

In the midst of this blog I narrowed it down, with some research to 8 main themes that get in the way. In addition or in lieu of these themes, I see really good people get stuck in not knowing how to vet for themselves on a date. There is a disconnect, as Damona Hoffman, author and tv personality dating coach would say, between how the person is authentically and how they convey themselves to others. 


8 themes that get in the way: 

  1. Those who are critical and self-deprecating 

  2. They are not good listeners 

  3. They are not able to let go of the single lifestyle  

  4. Those with too high expectations 

  5. Fear of intimacy 

  6. Have not done the work aka gone to therapy and sorted out your shit 

  7. They do not prioritize dating 

  8. Continue to choose the wrong people 


The Biggest Culprit: The are not good listeners 

Have you ever been on a date where the person across from you didn’t ask any questions? What was that like? Boring probably. Or you pipe in and they do not ask you a follow up question. Then you go home and receive a text saying “We should do this again sometime!” and think how in Heaven's sake could they think this date went well?? Sound familiar? This is how oblivious the importance of asking questions to someone else is with someone who has yet to learn the basics. The sad truth is that they are listening, but only to what they think is important: themselves. 


What’s the antidote to increasing the chances of a second date? 

People who ask follow up questions on dates are considered more likable than those who do not. Damona says it was less about asking the right question, while that is important, and more about the other person being curious that spiked interest and therefore to be date-worthy. 

But if you are wondering what to ask follow up questions about, before you go on the date, reread their profile and perhaps some of the things you started talking about on the app. This allows you to relate to them or talk about common points of interest, making the point of the conversation steered in the right direction. 

According to Damona she says the most important thing is to be genuine, compassionate, and create a comfortable atmosphere for you both to have an intimate conversation. People can tell if you are being fake and inauthentic. It isn’t a good look! 

So what makes it hard to ask follow up questions? 

It can attest to not the right chemistry- we’ve all been on dates or met someone where we just did not vibe, other times it is social anxiety and they talk and talk and talk and talk. This is particularly true when the receiver does not interrupt because you are probably asking them questions and so they have more to say. Hence why you might receive a text about how well they think the date went. Other times, the person is selfish and does not make an effort to ask questions, or last, the conversation stops flowing and you are blocked about questions. 

Post date self-reflection

  • Be curious about where you get stuck, if at all, and ask yourself if part of the reason you are not going on second dates is because of the above reasons. 

  • If you can come away from the date learning 3-5 things about the partner and knowing you shared 3-5 points about yourself, count it as a win. 

  • Be gentle with yourself, I am not exempt from saying stupid or weird stuff on a date that I probably should not have said or wish I didn’t say.

Here are some follow up questions for your next date: 

That's interesting, what was it like for you? 

Sounds fun, tell me more. 

How long ago did this happen? 

Would you ever do it again? 

How did you end up getting into that role? 

What is the story behind this for you? 

What do you like / did you like about it then? 

Would you do anything differently (next time)? 

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