over and under

I ended up in a generational divide-style dating conundrum this weekend.  On the one hand, I was being asked out by a 45-year old with a kid (The Lawyer), who I have to say isn’t really finding a way to my heart.  A very handsome yet still playful fellow sailor (Mr. Mexican Sailor), at 55, was a true flirt and knew how to handle a woman.  I had dinner with a married 62-year-old friend (really, truly), and we made fancy bourbon whipped cream for some imported strawberries while we commiserated on the lack of contemporaries for us to hang out with.

On the other side, my 26-year-old friend (Mr. Asparagus), who I’ve known for a while and with whom I have a lot in common, made some new overtures and had a nice dinner together.

I am loving the single life for the moment. It is good to take a break while I repair my broken heart and try to establish what I want.  Yet, a scene in the newest episode of Girls reiterated what I’d experienced this weekend. The two male characters chatted about how they couldn’t date the in-betweens – between “18 and 50” – because they were too into themselves and not insecure enough.

 It seems like these guys just don’t want to deal with women their own age who are inevitably struggling with the same amount of insecurities that the two of them are. I think they feel that older women and younger women are “easier” to be with because with younger women they get to feel like they have something to teach them — without really exposing their own insecurities — and I doubt older women care as much about those insecurities. It’s always scariest to be with someone who you really have to relate to.  HuffPost

I think I might be contributing to the problem – as I spent my weekend playing “over and under” too.  There are some 30-somethings in my life who are engaging and open and not so frustrated with women their age.  Hopefully I will get to write more about them in the future.  But most of the 30s-guys I know are:

  1. married or
  2. trying really really hard to not be married (see for instance Mr. Faraway, and many of my undergraduate cohort) or
  3. not feeling financially stable enough to even date.

Mr. Faraway always complained about the “expectations”. I guess that is where we lost each other.  He wants someone to have sex with when he comes home, and I want a best friend to build a life with.

My task for myself this week is to spend some more time imagining how to let myself be a little vulnerable so I can have a boyfriend who wants to be good to me, rather than a partner who needs to be pushed and pulled and coerced and manipulated into “declaring” an “us”.  As I kicked butt in the 8-mile Aloha Run yesterday (1:21!) I think this will have to be emotional vulnerability!  🙂


About tidewater

thirty-something, mostly single, finding a path.
This entry was posted in Dating, Relationships and tagged , , , , , , . Bookmark the permalink.

2 Responses to over and under

  1. Nice time on your run. 🙂

  2. Pingback: wherefore art thou… Romeo? | Uncharted Waters

mahalo for your comment!

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