My Bad Date Diary: Wicked Awful Time in Boston

By: Kevin Murray |

I like to pride myself as being great at online dating. I mean I’ve been on more dates than I can remember, studied it in college and I now work for eFlirt Expert. However, it doesn’t make me immune to bad online dates – sometimes they just happen, even to the so called “experts.” I usually don’t tell tales of my dates so quickly after they happen, but this chick really pissed me off.  What happened was so absurd I figured it’d be a good time for a little show & tell. Lets start off by setting the scene:

Location: The Warren Tavern, Charlestown, MA (Boston)

My Date: She was a cute brunette, aggressive and extremely witty through email and text – not to mention she sounded fine as hell on the phone (this chick was right in my wheel house).

Setting: It happened to be the same night as game 3 of the World Series. Never a great idea to go to a Boston Bar chalk full of Massholes during a major sporting event when you’re on a first date. But, like I said, the chick was hot and witty so I went for it. We were scheduled to meet at seven o’clock – here’s a timeline of events, painting a picture of how this horrible evening went down…

7:00PM – Drive by bar, call my date and tell her I’m near by trying to find a parking spot.

7:15PM – Say the F-word 5 times to myself realizing all surrounding streets are one-ways with  parallel parking only – my favorite. I’m from the suburbs, I hate parallel parking. So as I’m punching my steering wheel in frustration, this text message exchange goes down.


(Side note: When you’re an online dating veteran you keep track of women by using their first name and the site you met them on. Like Jill OkCupid or Jenny Match. This is way to keep track of who’s who in what can be a sea of text messages. To be nice, I blocked out this chicks name. Although, I’ll give you a hint and say it starts with Ash and ends with ley.)

7:33PM – My date calls me asking me if I’ve found a parking spot yet after texting me 3 times (Major red flag. You know I’m trying to find a parking spot so chill out sweet tits and let me concentrate. This car ain’t gonna park its self)

7:34PM – Stalk an old couple for 2 minutes and FINALLY find a spot.

7:45PM – Show up to my date location 45 minutes late, to no fault of my own  (The bar is packed – people jammed wall-to-wall. She’s looks just as good as her pictures if not better. And she got us a table top right in front of the  biggest TV, which is really the only thing she ended up doing right that night. We seemingly hit it off right away or so I thought…)

8:07PM – Red Sox game starts which means I only truly retain about 15% of what she says.

8:30PM – Get introduced to her roommate Catie (apparently they live 5 buildings down from the bar).

8:52PM – Find out my date is a former gymnast and think dirty thoughts about her flexibility for 10 minutes straight  the next 4 hours.

9:00PM – Random dude with a major Boston accent comes over and starts shooting the shit with my date and I while he watches the game. Our convo sounded like every cliche Boston movie you can think of. Pretty sure we set a record for the most F-bombs in 60 seconds.

9:15PM – Realize this girl is a major Pink Hat. She has no clue or cares about whats going on with the Red Sox game. This was supposed to be a sports date – I seem to be the only one holding onto that sitting there like a 12 year-old in my Pedro Martinez jersey.

9:24PM – Actually say to myself “wow, this date is going pretty good. I mean I can put up with the fact she’s a pink hat because she so hot and witty.”

9:30PM – My date says she got a text saying Catie isnt feeling good (Didn’t really think much of it at the time).

9:34PM – My date walks over to Catie whos standing with some other friends near the bar.

9:35PM – This random bro and I talk about how nice of an ass my date has as she walks away.

High five

9:44PM – Catie and my date walk back over to our table top. My date says she’s going to walk her home and will be right back. I give Catie a handshake and said bye.

9:53PM – I try to be witty and drop this text, followed by her reply.


We had an inside joke before we met that she started. Where if the sox hit a homerun I got to grab her ass, if they hit a grand slam it was a kiss and if we won it was everything at once.  Eh, well so much for the ass-grabs…


I really believed she was coming back . I didn’t want the vultures to steal our table so I held my piss and kept drinking so our server didn’t get mad I was hogging a whole table to myself. Really bad idea.



(The hospital. Really? I’ve been on a lot of dates and never seen some crap like this. Just tell me you don’t like me – I could give two shits.  My ego can handle it.)


11:00PM – After being alone for an hour these three chicks walk over and start talking to me. “Awe, did your date leave you? It’s OK, you can do better than her anyway. We can be your dating coaches.” Ugh, get away from me and just let me crush Bud Lights while I watch the Sox game.

11:02PM – The wife of the couple sitting next too us all night yells over in a  Masshole accent and goes “Screw her! You can do way bettah than that honey. She don’t deserve you!” Jesus, what’s up with these people? I must of had a huge look on my face that screams I’m pathetic.

11:25PM – Then this shit happens…

People in the bar start going nuts. One of the most controversial endings to a game in the history of sports and it happens to be against Boston in the World Series. So my date leaves me and the Sox just got screwed. Solid night.

11:30PM  to 1:00AM – I drink myself silly with the random dude that’s now sitting where my date once sat. We spend over an hour bitching about women and the Red Sox loss – twas a sweet bromance therapy session.

1:15AM – My new boyfriend walks me to my car because I have no idea where I parked.

2:15AM – Drink water/nap in car for an hour till I sober up, then bring my ass home.  Just your average night in the life of a scorned Boston bachelor when his date leaves him and the Sox lose game 3 of the World Series.

10:15AM – I wake up to this texual puke.


Save me the pity party. You’re not ready for dating huh? And you needed to talk to me for a week online and then waste my Saturday night to figure that out? Awesome. Not every date you go on is going to be a blast. Shame on me for giving her a date during a major sporting event. That’s like a rookie mistake in the Masshole handbook. I tried to parlay a hot chick and a major sporting event – you gamble big, you lose big.

It’s OK though. Four days later my night out in Boston ended much better.

World Series

 I should’ve worn that disco ball on my date. Chicks dig that kinda stuff right?