Dater X: The Un-Dateable Dater X

A few years ago, after an evening of sweaty, athletic, and very satisfying Naked Time, a card- (er, hose-) carrying member of the FDNY told me that he loved me.  My flummoxed response: “I really like you very much!” So it should come as no surprise that when the dating gods handed me a lay-up last night, I rattled it right off the rim and twisted my ankle on the landing.

Context: I captain a co-ed softball team that is loaded with attractive, eligible men.  I keep swearing off intra-team hook-ups, mostly because I’m sick of replacing players when it all inevitably goes south, but every season, I eventually abandon reason in favor of making out.  (Like the adult that I am.)  This year’s most promising candidate has played for years and suddenly feels more warm than distant.  We’ll call him Esquire, because he has a grown-up job and therefore makes little freelance writer me feel like a poorly trained puppy galloping around New York without a care in the world, occasionally peeing on inappropriate things.  He’s handsome and successful and a little quiet: a perfect storm of Things That Make Me Nervous.

This past week, I picked up a glove that was abandoned at the field after our game.  The commissioner posted a message letting the teams know that I had it, and last night, Esquire texted me to say that it was his.

Yes!  YYEESSSSSSSS!!!  Perfect excuse to meet up.  A+.  Brilliant.  And what did your Un-Dateable Dater X do with this serendipitous little morsel of catnip?

a) I offered to meet him after work one day this week to give him back his glove and grab a drink. (Pros: effective and to the point.  Cons: too forward?)

b) I politely said I’d hold on to it until our next game, a week from Sunday.  (Pros: gives him a chance to suggest meeting up sooner.  Cons: the possibility that he won’t.)

c) I made a crack about him not having any games between now and then – as in, “Loser!  Doesn’t everyone play on a dozen different teams?” – then made it clear that I was not available or willing to meet up and give it to him before our game.


Me: “We’re your only team, right?  You won’t need it before the next game?”

Him: “No, I’m good.  Will just pick it up at the next game.”

Me: “Cool.”

No, Dater X, NOT COOL.  I’m living in some kind of hellish limbo where I know I want to meet someone, but every time a potential suitor wafts into my orbit, I self-sabotage my way out of any potential intimacy.  If there’s a line between friendly and flirty, I can’t see it – and I definitely can’t find a graceful way to cross it.  Needless to say, I will not be seeing Esquire until our next game, at which time I’m sure I will clumsily preclude his ever suspecting that I’m interested.  Even though “I really like him very much.”

Great to meet you, readers.  Buckle up.  Where we’re going, we don’t need roads.  (We need lessons.  And a helmet.  And a cocktail.)

‘Til next week,

Dater X

[Image via Shutterstock]