Holden Caulfield: First Date

I was so right.

After a little bit of internal debate, I decided to meet Holden Caulfield for a drink the other night.

He texted me the night before:

HC:  Hey lookin forward to tomorrow, is like 9:30 okay?  I can pick you up wherever you are so you don’t have to worry about getting anywhere

Me:  Sure!  (But a little confused) What do you mean pick me up?  Like in a car?  (See, in the City, you usually just go out and meet men on dates.  Most of the time, they don’t offer to pick you up.  And although I lived in Minneapolis and dated a bit there, where the men would drive and pick you up in cars, this is still surprising to me since I identify with dating mostly in NYC.  The only other men who picked me up in their cars was 1) a millionaire who had sold his startup and told me how much money he made from it and 2) My Mr. Big (MMB) who I dated over the summer and drove an M5)

HC:  Yep

Me:  Oh wow, that would be so nice of you!!

HC:  Cool 🙂 see you tomorrow!

The next day I wasn’t feeling very well and could feel a cold coming on (itchy throat and ears) so I texted Holden Caulfield. . .

Me:  hey there are you available for drinks on Friday instead of tonight?  I developed a sore throat and would like to get to bed early.

HC:  No problem Friday I have my friends bday dinner and will meet you after.  But aww man was excited to see you.  Feel better and hopefully we can chill Friday if not brunch Saturday!

Me:  Hm well I can go out tonight but just not stay out too late?  (I just wanted to get the date done and over with)

HC:  Yea take a nap and lets just meet for a bit I won’t keep you up late promise.  We can go somewhere close to you

So, Holden Caulfield was a half hour late to pick me up.  I have a sore throat, I’m tired.  I’m not happy about this.

HC was really apologetic and nice and normal.  But he pulled up in a car service car, which was not what I expected.  He explained that he does have a car that he keeps in the City but didn’t want to bring it out.  I didn’t want to engage in too much conversation in the car in front of the driver because I just felt embarrassed that I was going out with this guy I met once, randomly on Thompson Street.

We arrived at a cute little wine bar just 5 blocks up from me.  I had no idea this place existed.  HC picked it out.

So, we sat at the bar and debated sharing a bottle of wine.  It’s already past 10pm.  We got a bottle of red wine.

We engaged in some normal conversation, catching each other up on our life events over the past month and a half since we met.  He told me about the work he does and I told him about mine.  HC works in the world of finance.  Go figure.  But the work he does is cool and on the cutting edge.  And he loves what he does so I found that to be very refreshing and nice to listen to.

Then. . .

HC:  So, when did you move to the City?

. . .

. . .I’m staring blankly at him. . .

. . .

Me:  (meekly) I think I’m a little older —

But before I can finish, HC interrupts me  —

HC:  I know.  (Nonchalantly)

Me:  I’m older than I think you think I am.

HC:  I knew you were older.  I don’t care.

. . .

Me:  Ok, I moved to the City in 1998.  (And I cringe, slightly)

HC:  I don’t care.  I have friends that are older than me.  “So-and-so”, my good friend is like 37.  Except for my high school friends I have a ton of friends in their 30s.

Me:  Are you even 30 yet?

. . .

. . .

HC:  (smiling) Almost.

But as we are talking, we’re joking and laughing and HC is cracking jokes left and right about this whole age thing.  And his sense of humor is good:  witty, light, jovial.  Just trying to make light of the situation so I don’t feel awkward.  Just being very considerate of my feelings.

HC:  I was thinking to myself — “Oh in 1998, well I graduated high school in 2004. . . ”

OMG, he graduated high school in 2004.

HC:  But then I thought, “OH wait. . .”

So, we’re sitting there laughing and I’m still feeling a little uncomfortable, and HC can sense this so he says. . . “The only way to make this better is to just make out right now.”

We laugh more.  I’m not making out with him at the bar.

HC says, “I like your laugh”

Me:  (I stop in my tracks, tilt my head sideways, and sincerely) Thanks.  [Smile]

We carried on with the wine and talked about all kinds of things.  His sense of humor was on the same wavelength as mine and he seemed so happy-go-lucky.  Not jaded.  Not cynical.  Not resentful.  Nothing like the 40+ year old men I’ve dated.  Just so refreshing. . .

HC:  Your hair looks different than when we met.

Me:  Yeah, I straightened it.  It was curled that night.

HC:  (very matter of fact)  I like it.

Then somehow we got into vacation spots.

He loves the beach.  So do I.

HC loves Hawaii.  So do I.

HC grew up surfing.  OMG.  I started surfing 9 years ago.  Music to my ears.

HC:  Can you surf waves that are around 4′?

Me:  Biggest waves I’ve surfed were around shoulder height.

HC:  That’s not bad.  Maybe about 5′.

Me:  Occasionally I’ll go smell my wetsuits in my closet because I miss the beach, water, and waves.

(Oh no, maybe that made me sound like a weirdo).

It was time to head home.  It was getting late and I was out later than I wanted to be, though we were having fun.  I suppose all good things must come to an end.

Holden Caulfield walked me home.

Smile, Adam!

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