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Jewish Singles: Red Flags

I must share with you all a date that I had recently.  We will call him “S” and I will start by saying “OY.” 

This guy took the cake.  We chatted on the phone for about a week, prior to our date.  He had a very deep, sexy voice that I was immediately drawn to.  He owned his own business and seemed to do well for himself.  So, he asks if I’d like to hear him play his guitar.  I found it a bit odd, but said ok.  “S” proceeds to serenade me via telephone with his guitar.  Don’t get me wrong, he was great, but he kept going and GOING.  Like, he could have played forever had I not interjected with a “That’s great”, or “Very nice.”  So, we planned to meet on a Saturday night.  He picked the spot.  It was a restaurant called Lincoln, a new, hip place.  He greeted me at the bar with a nice hug.  From that moment on we were joined at the hip.  We had steak and drinks at the bar, sitting very close and flirting like crazy.  I was thinking that it couldn’t get any better or feel any more comfortable.  Conversation was flowing, compliments flying, and I was thrilled.   

UNTIL…..RED FLAG ALERT….He proceeded to tell me that when he was 16, his father overdosed on his mother’s anti-depressants, killed her, and then killed himself.  UM.  I’m sorry….WHAT????!!!!!!  Don’t get me wrong, it was tragic and my heart went out to the guy…but I’d say that was TMIFAFD (Too Much Info For a First Date.) Oh, it get’s better.  “S” was married to a woman who tried to commit suicide numerous times and finally ended up in a mental institution.  Now, by this point, I’m a bit tipsy.  So, his revelations didn’t effect me as much as they would have had I been completely sober.  He reassures me that he is “just fine” due to a lifetime of therapy.  GOOD LORD.  So, one would think I would be completely frightened by this point, but one apple martini later and I was ready to hit the town!   

We went to a cool jazz club for coffee and dessert.  I tried my best to focus on the good time I was having despite what I had heard earlier.  After about an hour, we decided to call it a night.  He drove me to my car.  We chatted for a bit before saying goodbye.  Well, he saved one more juicy story for the grand finale.  I had the privilege of learning that he was de-virginized when he was 15 by his father’s married secretary.  (I’m sure all you guys are saying “cool, what a stud!”) He gave me more sordid details that I just don’t have it in me to reveal.  Needless to say, I was very surprised, yet intrigued, in a twisted sort of way.  We had a nice kiss goodnight and that was it.  He called me the next morning to say he had a great time.  I was pretty impressed at the timely manner in which he called.  Most of the men I had met from a certain well-known Jewish dating site were as flaky as could be.  So, he scored a few points there.  He asked me out again, and for some odd reason, I accepted.  I guess it was the romantic in me, choosing to ignore the red flags, and proceed on.  Ladies, we’ve all done that, right??   

He picked me up on our second date.  I got in the car to find him very different than he had been 2 days prior.  He claimed to have a headache.  But he was eerily quiet.  We had dinner at Senor Fred.  He was quiet most of the dinner, and stared at me in a very creepy way.  Finally, I said, in what I thought was a cute, charming way…”Yes?  What can I do for you?” (batting eyelashes.)  Well, was he offended!!  He chastised me for making a comment like that.  I was completely dumbfounded.  I explained that he was making me uncomfortable staring at me like that.  My comment was a playful attempt to get him to STOP.  He said he just liked looking at me.  Well, needless to say, the rest of the night was a complete downer.  He seemed very depressed and all around weird.  I think we both knew that we wouldn’t be seeing each other again.  I emailed him the following day to thank him for dinner, just to be polite.  He wrote back saying, “You’re welcome.  I enjoyed our time together.”  So, we had one good date and one completely odd date.  I guess it all worked out for the best.  I mean, how many red flags can a girl handle, after all??  I’ve since learned to pay attention to the red flags and not let physical attraction overtake my better judgment. J 

Till next time,  



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