The Tale Of The Great Escape

The Cast:

  • Shadow – my date
  • Roommate – my roommate
  • The Work Crew – coworker/friends


I met Shadow in grad school about a year ago.  I hadn’t seen him in months until I ran into him on New Year’s Eve at Tavern On Broad.  We got to chatting, exchanged numbers, and made plans to meet up later in the month.  He is in his thirties so I figured it would be a nice change of pace from the guys I’d been meeting recently.

ACT 1 – The Date

Shadow and I made plans to meet up on Saturday night in Center City.  I took the train downtown and he offered to meet me at Market East so I wouldn’t haven’t to walk alone. <bonus points for him>  We decided to go grab drinks and watch the Ravens/Broncos game then follow it up with dinner.  <once again, bonus points for him for being decisive and taking charge of  the evening>  We met up pretty early and since it was a first date I didn’t expect to be out too late.  My hope was to take the 9:30 (10:30 as a back up) train out of the city later in the night.  Well the football game went into double overtime so we didn’t even make it to dinner until after 9:00, and by that point I was relatively sure I wasn’t interested.  Shadow was a nice guy and we were having a fun enough time, but he committed quite a few of my “first date no-no’s.”  I know that might seem a little judgmental, but first impressions really are important.

So now I’m sure you are shaking your head and thinking to yourself Really hun?  First date no-no’s.  No-no wonder you’re still single!  But just hang with me here…

  1. He used to F-word multiple times.  I know, I know it’s just a word, but I don’t see the need to throw foul language around in public, especially when you’re with someone you don’t know well.  Cursing should really really be kept to a minimum on a first date.  Here’s a good rule of thumb, if you wouldn’t say it to your mom, then don’t say it on a first date.
  2. Too Much Life Story (TMLS).  This one can seem a little contradictory because I really do want a guy to be honest with me.  I want to get to know him, but there is something to be said for leaving a little to the imagination on date #1.  I enjoy hearing about your past, but here’s a hint, if you’re divorced, keep the ex-wife talk to a minimum on the first few outings.  Whoa.  T M L S.
  3. He drank a lot!  Another of my first date rules of thumb is to keep the alcohol  consumption to a minimum (the word minimum seems to be a trend here).  I like to have a few drinks, but I make a very conscious effort to  drink less than I would on a normal night out with friends.  I’m trying to get to know a person and  I don’t really want my judgement to  me impaired.  And I don’t know, call me crazy, but there is nothing attractive about watching a grown man slam 20 oz Miller Lite drafts, even if there is a playoff football game on the TV.
  4. A weirdo 50 Shades of Grey reference.  This part came late in the night and I don’t even remember what he said exactly, but it definitely had to do with my scarf and bondage.  Seriously dude, we just met!  I get that you’re probably joking, but it really wasn’t funny.  At this moment I knew it was time to plan The Great Escape.

Do these  rules seem a little harsh?  In all fairness, if I find myself having a super strong desire to kiss you, then that will trump the “no-no’s” that have been committed.  I’m not going to kiss you, because I don’t kiss on first dates (see, there I go with those rules again!), but if the desire is there, I’ll probably (for better or worse) still give you a chance.  Unfortunately with Shadow, despite the more-beers-than-I-usually-drink-on-a-date-scenario, I didn’t have the I-want-to-kiss-you-now-urge, so I knew the night needed to come to an end.

ACT 2 – The Great Escape

While Shadow was in the restroom during dinner, I checked my cell phone and noticed some text messages circulating between Roommate and The Work  Crew.  They were making plans to go to Finnegan’s Wake, which happened to be a few short blocks from where Shadow and I were eating.  We’d  been out for nearly 4 hours (plenty long for a first date!) so I was ready to call it a night.  When Shadow came back from the bathroom, he looked at the time (it was already 10:30!) and mentioned that it looked like I had just missed my train, so he suggested we go get another drink, then he’d walk to me to Market East to catch a later train.  I was armed and ready, explaining to him that Roommate was over at Finnegan’s so it just made sense for me to go meet her there so I wouldn’t have to ride the train alone at night.  The perfect excuse to peacefully end the date!  I was feeling brilliant!

“Oh, that sounds like fun!” Shadow said, “let’s walk over there and meet them.”

What???  He wants to come with me!?  That wasn’t an invitation.  That was a rejection.  

Man, I suck at dating.

Shadow paid for dinner <bonus points again… but too late to salvage where the evening was going> and we made our way over to Finnegan’s to meet Roommate and The Work Crew.  One of my favorite cover bands, Secret Service, was playing so all I wanted to do was be-bop around the dance floor, singing along with my friends, but I kept feeling like I had to entertain Shadow.  Oh yeah, that’s how he got his nickname.  He kept hanging so close (like right on me) all night, that when he finally left to use the restroom, my friends asked me where my “shadow” went.

After about an hour and a half and a lot of lower back rubs and that weird 50 Shades Of Grey comment, I knew it was time to ditch him for real.  I wanted to be somewhat respectful about it so I did refuse my friend’s plan to “go outside for a smoke” (aka hop in a cab and drive away) and came up with something mildly more mature.

The Work Crew secretly picked a new location for us to go in Old City, then Roommate came over to me and announced that she was tired and ready to go home.  I “reluctantly” agreed and told Shadow it looked like my friends were ready to call it a night.  We  all made our way out front where I politely gave him a hug and thanked him for a nice evening, then made my way up Spring Garden with Roommate to try and find a cab.  Shadow walked down Third towards his apartment and as soon as he was out of sight, my friends and I all piled into a cab and rolled south into Old City to finish off our night at Bleu Martini (and that…well…that is a story for another day).

My friends and I are logistics managers by day and it took  six (SIX!!) trained logisticians to sort out a way to end my date with Shadow.  A true testament to Shadow’s effort… or a pretty negative reflection on our ability to do our job… you decide.

And in case you were curious, no, there was not a second date.

My quest continues!!


In all fairness to Shadow, he really did pique my interest in the idea of dating guys in their thirties.  He was direct and to the point, asking for my number then asking me out.  None of that annoying chit-chatty texting for weeks, waiting for me to suggest that we “hang out” some time.  When we did go out, he took control of the date and made plans, instead of pushing it back on me to decide.  It proves that he has a) been on dates before and b) knows how to be a man.  Finally, I’ve never had such an easy time of ending something.  Instead of hem-hawing around and small talk texting me day after day, he simply asked me out again.  When I said, thanks but I don’t really see this going anywhere, he didn’t get offended one bit.  He told me that he had fun, but no hard feelings, and he’d be more than happy to just be friends.  Simple, to the point, and no drama for once.  <bonus points for Shadow!>

Have you ever been on a date that never seemed to end?  What are your first date no-no’s?  Or am I the only person with a list of insane rules?


Tall  One


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s