My Longest Relationship Since High School

It was six dates.  Sad but true.  And a little bizarre I have to say.  Maybe our personalities didn’t match or maybe there was more going on beneath the surface.  Take a look at the dates and communication and see what you think.  Any insight is appreciated.

Background: He winked at me on Match.  I responded.  We exchanged a couple e-mails and decided to meet up for lunch on a Saturday.

Date #1: He’s an attractive man, 29, a little taller than I am which I appreciate.  He’s driving a small pickup truck.  Another thing I appreciate.  It’s a noon date so I’m fine with his khaki shorts and polo.  We meet at the local Italian chain restaurant and engage in the get-to-know-you stuff.  He’s a history teacher and football coach at a local high school.  He just moved back into the area to be closer to his family.  He loves football, especially one of the big college teams.  That’s par for the course anywhere but especially in the South.  That doesn’t bother me.  I’m a big fan of the NFL just not so much college.  Anyway, we have a nice lunch and he pays. 

I think it went well but I’m not too hopeful because of how other first dates have gone.  He texts me the next day.  We have several text conversations through the week and make plans for the next Saturday.

Date #2: We meet for lunch again.  This time at the local sports bar and restaurant.  Then we see an afternoon movie and I go home.  Nothing eventful.

We text again all week.  I’m really enjoying the conversations.  They get a little flirty.  That’s probably why I agree to the third date.  I keep thinking, “He must be into me.  He keeps flirting over text and asking me out again.”  So we have a third date.

Date #3: He invites me to his apartment for pizza and football.  That’s cool.  I head over to his apartment late afternoon.  We sit on his couch and talk about random stuff.  Football in the background.  We pick up a pizza, eat, talk a little more, the real game comes on, we talk during the commercials and then I leave.  Yeah, no real chemistry happening.

I’m a little confused at this point because each week over text he’s flirting and it seems like we have some things in common.  I think, “Maybe he’s just shy.”  So I forge ahead.

Date #4: The next Saturday, trying to avoid another boring and slightly awkward evening of football and stilted conversation, I suggest we go out.  It’s fall and a local farm has their corn maze set up.  He’s not too keen on the idea.  He has mentioned several times that he loves to just “chill on the couch” and when there’s a slight chance of rain on Saturday, he tries to get out of going.  I insist and we head to the corn maze.  It’s not what I had hoped.  My plan was to get us into a walking side-by-side situation where either he would hold my hand or I could take his and try to get something going.  The maze was narrow, allowing barely enough room to walk single-file.  I’ve also learned I’m really not good at mazes.  We found our way out and went to eat.  (We didn’t make it to the end.  We retraced our steps to the beginning.  Pathetic, I know.)  We had a lack luster dinner and I went home.

This week same as before.  We find out that our birthdays are only three days apart and are happening that week.  So we plan a combined birthday celebration for the next, wait for it, Saturday.  (He was a football coach so he was a little busy on Fridays.  I was cool with it.)  I must admit I was almost over it at this point.  But it seemed wrong to breakup with someone on his birthday, so I went ahead with it.

Date #5: I was sick of meeting in the daylight because I believe that dating should involve sexy outfits and heels, which are usually too much for a noon-time lunch.  His suggestion is another trip to the sports bar for wings but I really just can’t handle that.  I insist on a nice dinner at my favorite hibatchi place and an EVENING movie.  Come on, this is a birthday for crying out loud!  Can we please for once date like adults and not teenagers who are getting dropped off by their parents and have to be home before dark?  So we do.  I even get him a present.  Salt and pepper shakers with his favorite football team’s logo.  Not great, but I didn’t know him very well.  He said he’d give me my present on Monday, which was my actual birthday.

Monday:  A lovely bouquet of flowers arrives at my office with a sweet note.  He’s been talking about taking me to a college football game because he’s sure that I’ll love it and there’s one coming up that Saturday.  His family has season tickets.  I decide to give it one last shot.  He did send me flowers, after all.

Date #6: Long boring car ride, even longer tailgate and football game, extremely long wait at a restaurant afterwards, and a traffic jam on the way home.  I never have understood the cult of college football and now I know that I will never understand it.  The conversation was like talking to a co-worker not a date, I had to meet his parents (waaayyy too soon for that), and he never once tried to hold my hand or anything.

The next day, I sent him a Facebook message and politely told him we didn’t have anything in common and I wanted to stop seeing him.  He said he agreed.

Soooo, what?  He’s just not that into me?  What was with the texting all the time and the flirting and always asking for another date?  And flowers on my birthday?  That all pointed to him being into me but when we were together he never once made a move and he always wanted to just get lunch and go to a matinee.  Or just “chill” at his apartment.  Was he not over somebody, was he gay, or was he just that devoid of personality?  This was just confusing.  But I’m glad I made the effort.  It wasn’t much but it was a learning experience.


2 comments on “My Longest Relationship Since High School

  1. writingbolt says:

    Two different people with different expectations. Two sticks trying to make a fire. But, you were both wet behind the ears. Neither could fully adapt or compromise with the other. You wanted candlelit dinners and hand play in the dark. He wanted to take it a little slower and stick with the daylight for a while so not to pressure you into a sexual situation. Yes, surely, he was shy on the surface and flirting from a distance to let you know he had some interest. But, sometimes, the flirting is forced, too. Maybe he felt pressured to keep in touch lest he loose his balloon.

    Not the worst or best outcome.

  2. […] else to say to a girl you’re supposedly trying to date? I went on five dates with an actual high school football coach and he had other things to talk […]

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