Detours and Derp

I’m going to admit two things.  First, I occasionally take detours from the search parameters for Man TBD and try something (someone?) new. I also am not good at dating (Shocker!).  I have therefore adopted this video as the summary of my dating strategy and success:

I have some successes, but I haven’t found a way to make it truly satisfying.  But I’m not drowning and I’m not going thirsty.  (That is deep.)

Anyways, this weekend, I took a detour with, IMO,  hilarious consequences.  Saturday night, I broke a rule and decided to go grab a drink with this guy who first started messaging me Saturday afternoon.  He didn’t seem creepy and I my only plan was to play with my new iPad, so I decided why not!  But why the rule?  Well, if a guy wants to see you that quickly, he usually has an agenda and by accepting, you show some desperation.   But, I thought rules be damned!  I shall test the rule and see what happens!

I show up at the appointed time and he is nice enough, albeit it a bit overly energetic for my tastes and shorter than he claimed (*Note that men tend to exaggerate height online and it’s because women–I’m guilty–tend to filter for certain heights and above, but if you say you’re 5’9″ and you are 5’7″ and the woman is actually 5’9″, then she’ll actually notice that you are not 5’9″, but I digress again*).  Quickly, the conversation gets sidetracked when he asks: “What is the craziest thing you have done in the last month?  Like you know, maybe you had sex outside somewhere.”  I quickly say: “Well haven’t done that… gee I don’t know let me think.”  Brain begins to kick into overdrive:

Wow.  Ok.  I… um…. f@ck… I work too hard so the answer is really something along the lines of I made signature pages because I forgot to ask my junior to do it and it was midnight and I promised them to a client.  That’s not even crazy.  That’s just an example of poor planning.  This is a perfect example of why working too much can be a con in dating even if you find time for a date!  Nothing to say!  Can I say that I totally fell for a guy and continue to cyberstalk him.  No.  I don’t think that’s the right kind of crazy.  Wait.  I don’t even want to answer this question in any legitimate way.  

“You know, I can’t really think of anything.  I’m not really the crazy type and generally I just work a lot and go to the gym, to be honest.  So do where are you at with your PhD program?”

Good back on normal conversation, though obviously this isn’t going to work.  Two beers max then HOME.

Conversation continues with a few more speed bumps, that I try to maneuver.  Why won’t he take the hint?  And then we get to: “So, I like to live in the moment.  Just enjoy every moment of life.  I’m not looking for anything serious.  I don’t like drama.  I mean I think you’re pretty and fun.  I’m really enjoying myself right now having this beer.”

I am shocked.  Utterly shocked.  NOT.

“Well, I, um.  I also think you’re really fun… and clearly very positive.  But, to be honest, I am looking for something more serious from dating.  You know, I’m just ready for something real.”

Good.  Intentions made clear. We can wrap this up in short order.

So I go to the bathroom and the check comes.  I finished my beer and he doesn’t have much left.  And. Then.  He begins to pet my arm.  I’m not talking some sort of sexy “petting”…. I’m talking this:


This isn’t happening.  What is happening?  He can’t be petting me. Oh, GOD!  He is trying to make eye contact.  He is petting you and trying to make eye contact.  Can I just move my arm away?  Ok trying that.  He’s moving with it.  Don’t you laugh.  Stop.  Do not laugh at him petting you…

OMG he’s petting me…He keeps trying to make eye contact and now he’s using both hands:



<<ha….argh… cough>> “Um… so do you usually pet your dates?”  <–this one is an exact quote.  I couldn’t contain myself.  

Him: “What you don’t like this?”

Me: “Um… well… You know I’m going home alone tonight, right?”

Him: “You don’t like this?  I’m just enjoying the moment.  It doesn’t mean I have any expectations.”

Me: “Um… Well I’m not going home with you and um… no one has ever done this to me before….”

Him: “C’MON!  Seriously?”

Yes.  For f*ck’s sake, yes.  I’m in Puritan New England and I’m not hugely into touching strangers, but this is not normal, nor really doing anything for me in a sensual way. 

Him: “Who are you dating?!?”

Not you again.

Him: “Wow.  It’s just something nice to do.”

I black out from suppressed laughter at this point.  Some rules aren’t meant to be broken. 

Now, I’m not particularly proud of this part and I was going to filter it, but it happened.  I realize that (a) it’s pretty early, (b) I’ve been kind of bored lately, which is why I’m even on this date in the first place, (c) it would be nice to stop thinking about Him #1, and (d) he doesn’t want something serious so it’s not leading him on.  So, I say: “Would you like to go makeout in an alley?”  Clever and smooth, right?  He says: “Sure! Can I hold your hand?” Do you have to? “Sure…”  So we do and he pretty immediately starts putting his hands where they don’t belong…. so I am like this the whole time:

Source: Cute Animal GIFs on Tumblr

Now this is the part I’m really not proud of…..

Well.  This is OK enough for a makeout session.  I’m not 100% into him, but it wouldn’t be leading him on if I did go home with him since he doesn’t want anything serious.  I never have actually had a real one night stand.  Maybe I should give it a try since there isn’t a risk of me developing any real feelings for this guy? YOLO?  

Him: “You are a good kisser.  Like a really really good kisser” <–this one is also an exact quote and positive feedback is so nice to hear.  

Me:  YOLO! “Well, f*ck it, I never do this, but let’s go back to your place.”

Him: “Oh.  Wow.  Um.  Well you see.  My roommate is having a party and there are a lot of people over.”

Me:  Really?  Seriously?  “Oh. Ok.  Well I guess we could go back to my place.  My brother is staying with me, but I can tell him not to come home for a bit.  You just can’t stay over.”  Why is this difficult?  

Him:  “Oh.  I’m not sure I’m comfortable with that.  What about tomorrow?”

Me:  No way.  I’m not going to plan a one night stand.  That is not how this works.  “Oh.. No.  I understand if you’re not comfortable and it’s fine either way, but this is a one time deal kind of thing.  Living in the moment, you know?”

I got on my train, went home, and felt oddly uncomfortable petting my cats.



5 thoughts on “Detours and Derp

  1. OMG!!!! The petting is totally weird. Like someone double dared him to try it. I was cringing at where I thought the story was going and now I’m strangely relieved that somehow O., of all people, saved you from that! Ick.

    1. He is occasionally useful for something! I forgot mention that this guy had also at some point asked me if I would rather have sex in front of my brother or not have sex for 5 years. Again. Really happened. Couldn’t make that up.

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