Photo Credit: Jewish Press

Dear Dating Coach,

I have been dating for a while, but seem to consistently get the same feedback: not personable. It is true that it takes me a while to feel comfortable with new people and I am not the most outgoing guy. Yet, even though I am on the quieter side, I still enjoy a good conversation and I am committed to finding my right match – if only someone would give me a chance! I don’t need or want to be the life of the party or morph into Mr. Social, but I need help connecting with the girls that I date so they can see that underneath my reserve, I am interesting, kind, and even funny! How do I get my dates to see past my initial reticence to see the good guy that I am?


Irked Introvert


Dear Introvert,

I have been conducting an experiment for the past week. My hypothesis was weak, and the results were highly disappointing. There has been a sock on the floor of our laundry room for seven days. That’s 168 hours (Yes, I Googled it) of a sock coma that no other member of this household seemed to notice. At my first sighting, I bent down to save the sock from certain death and loneliness, but decided instead to conduct this valuable study for the sake of science (I know, one Nobel Prize coming up!). Now, every person in this house walked through the laundry room in the week of the sockness monster, to get a drink from the extra fridge, to get the hula hoop (I also don’t know why it’s in the laundry room), or to get yet another roll of paper towel (yes, we use too many). Yet, none of them picked up the sock as it lay there in pain, waiting to be reunited with its pair. It was stepped on, pushed to the side, and completely invisible to my sharp, eagle-eyed (oblivious) family. After 10,080 minutes (ok, I’ll stop), I waved that white sock-flag and called an in-person sock meeting to set my household straight. I think they get my sock commitment now and we can move on to single sink spoons left to linger…


Introverts Were Social Distancing…

I’m so sorry you are having a difficult time. It is frustrating to excitedly anticipate a new date and plan for it, only to struggle through your time together. You have good intentions and hope to find your zivug, only to battle for conversation and connection once you are in the same room. Maybe you over-think every discussion, worrying over your words, squashing any potential witty response from entering the conversation. Perhaps you freeze up, wanting to appear relaxed, aware that you are instead tense and stressed. I imagine that despite your best effort, you feel like you are failing to connect, and the more you worry about it, the more distant and disengaged you seem.


Way Before It Was Cool.

You want to connect, and that in itself matters. I would suggest that you make and follow a P.A.C.T. in order to help you succeed in forging a true connection with your dates.

Prepare: Before you go out on a date, brush up on current events, funny anecdotes, and interesting work stories. If you prepare properly, you will arrive on your dates armed with built-in conversation at the ready. You will not struggle to think of something to say if there is a lull, because you will have prepared an arsenal of easy talking points.

Appearance: On the date, make sure your appearance reflects interest. Sit up straight, make eye contact, and remain engaged. Smile, relax your shoulders, and breathe. Do not slouch or lose focus, and keep your phone out of sight.

Curiosity: Remain curious throughout the date. Ask questions that show you are listening and interested to learn more. If you lead with curiosity, your date will feel motivated to share, thus encouraging a connection.

Tone: Finally, monitor your tone throughout the date. Your tone should highlight your enthusiasm, care, and attentiveness. A low or bored tone, a monotone, or a strident tone are not going to get you far. This P.A.C.T. will help you to connect, increase your likability, forge a real relationship, and ensure that you are noticed and given the chance you certainly deserve.


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Henni Halberstam is a Dating and Marriage Coach whose expert advice will help you navigate dating and relationships in order to ensure a successful marriage. You can contact her at to schedule a phone session.