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Ask The Expert: Should You Go On A Second Date With Her?

After an awkward first date, is it worth going on a second one?


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Dear Carol,

I have been casually flirting with a woman I see at least a couple of times a week at the coffee shop underneath my office building. She finally had the nerve to ask me out. We had dinner after work and it was awful. I can’t even count the uncomfortable silences I had to fill. The awkward moments were overwhelming. I was quite shocked when she asked me out again next week for cocktails. My first reaction was to just say no. After a little bit of thought, though, I realised that maybe I should give her a second chance; one more date. Isn’t everyone entitled to a second date?

Sincerely,

Indecisive

 

Dear Indecisive,

To be truly honest with you, first dates are usually not great.  It is really hard to put your best foot forward when you are a little bit nervous or shy. It took a lot of guts for her to ask you out in the first place, which should perhaps warrant a second date. The pressure to say the right things instead of the wrong ones makes it impossible for some people to truly relax and be themselves on the very first date. They want to come across as confident and secure, intelligent and funny... the list goes on. If you grant them a second date, the ice has already been broken and you are letting them know you are a little bit interested. You will have the opportunity to get to know the real woman underneath the awkwardness. Love and infatuation are two different things, and the butterflies you feel when you meet someone for the first time are not often what truly sustain a long-term relationship. You enjoyed flirting with her, now give her the opportunity to show you her true self.

Love doesn't always happen on the first date. The best relationships take time, and with a little patience and understanding, love can grow.

Best,

Carol


Carol Sugar-Burke is an Executive Matchmaker for NY’s premier gay and lesbian matchmaking service Bespoke Matchmaking. 

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