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Home-Dater

By Henni Halberstam

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November 20, 2025, 9 AM ET

 

Dear Dating Coach,

I am really introverted. I prefer staying home over going to any party. I feel overwhelmed in a crowd, and I am happiest with my own company. I have a small, close-knit group of friends, I love my family, and that’s really enough of a social life for me. Now that I am dating, I have realized that my introverted personality is a detriment to this process. I struggle on dates with what to say, and with maintaining an easy rapport. I feel like my dates have been stilted and awkward, and I know that I am mostly to blame. I have gotten a few “no’s” after dates, and frankly, I can’t blame them. This is who I am, an introvert. Now what do I do?

Really Reserved

 

Dear Reserved,

Dating can be hard for the most outgoing and gregarious, as you meet someone brand new and are required to make conversation for hours. For an introvert, dating can be painful, as they struggle to overcome their innate reserved personalities. Still, we want both the extrovert and the introvert to meet their matches, and that requires dating. There are some things you can do to ease the stress of dating, so that you can still connect organically, albeit with some groundwork in advance.

 

Sorry I’m Late, I Didn’t Want to Come.

Prepare: Before you go out with someone new, prepare for your date. This is not inauthentic, this is smart. Think about which topics of conversation might serve you well on your date and have some talking-points ready to go. Formulate questions that you hope to have answered, and organize your thoughts before going out. Focus on funny or interesting stories that would be appropriate to share and conversation starters created to encourage discussion. This preparation will offer you both the confidence and the practical ability to converse with ease and to share when you might otherwise feel tongue-tied.

Tools: Today, you can easily find easy and acceptable games to bring on a date. Many daters find that simple card games with questions and thought-provoking statements allow an otherwise timid couple to connect. These tools take some of the work and pressure off of the daters and they fill in the gaps of conversation. Using these readily available discussion cards can offer a fun and easy exchange that leads into even more spontaneous dialogue.

Engage: You are an introvert and dating might be harder for you than others, but you must still fully engage on your dates. Focus completely on your date and listen carefully to what he shares so that you can respond in turn. You are not able to detach simply because this is a struggle. Engage fully and be present with your date so that your intention to connect feels clear. Participate with purpose, and your date will take note. Your ability to engage while dating will allow you to slowly form a relationship with someone new despite your reticence.

Take the time to prepare, use the tools at your disposal, and engage fully, and we hope that you will find the right match for you. We are rooting for you.

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