Dating Disasters- Wing Man in NYC

During my recent whirlwind trip to New York/Connecticut, I experienced the single most hilarious disaster I've ever encountered as a wing man. My train arrived at Penn Station at 1:30 am; pretty late by most standards, but for New York City, the night was still young. I met up with MaryAllen at a trendy little bar in her neighborhood and proceeded to fall in love with the smoking hot bartender while she and I sipped cocktails and made final plans for the rest of the weekend.

Out of nowhere this adorably awkward and very intoxicated tall dark and handsome fellow bumbled over to our corner of the bar and proceeded to shower my dear friend with grand compliments and proclamations of adoration. This guy was no slick willy, so the fact that he was laying it on thick wasn't off-putting in the least. It was just the opposite. He managed to be belligerently drunk but somehow endearing and cute. (Pretty sure I didn't know that was possible) I'm certain that he'd been enamoured with her all night and had taken the liquid courage route to work up the nerve to stumble over to her.

About halfway through his speech about MaryAllen's captivating beauty, he looked over and noticed that she wasn't alone, that she in fact had a wing man (me), a detail that I'm positive had escaped him up to that point. He gave me a dismissive but polite acknowledgement purely for her benefit and I giggled and turned my attention back to the bartender. I glanced at Romeo and his Juliet a few times throughout their exchange of bar banter, both fighting to be heard over the music, and things seemed to be going well.... when suddenly.....

Romeo leaned in to speak closer to his Juliet's ear and it was suddenly clear just how terribly drunk he truly was: HE HEADBUTTED HER. Perhaps it was his unsteady stance, his lack of depth perception, or maybe he was just that awkward. I have no idea...all I know is that it wasn't just a little embarrassing bumping of foreheads. It was a full on headbutt that caught both parties by such surprise that his head seemed to ricochet off of hers! The faces of the aftermath brought "deer in headlights" to mind...

Now I am not the kind of girl who likes to laugh at the embarrassment of others. I NEVER laugh when someone trips and falls because I'm usually too concerned they are hurt and it doesn't occur to me to laugh. So when our poor Romeo tried his damnedest to apologize and continue the conversation as if nothing happened, I did my level best to do the same: avert my eyes and pretend nothing happened. I had seen nothing.

For whatever reason, this was completely impossible. I fought the laughter so hard that I thought I might break a rib, and of course the harder one tries to stifle a belly laugh, the more hilarious the situation becomes, and so with the best of intentions I destroyed all the wooing Romeo had tried to do. I turned my back on the two lovebirds so as not to laugh in their faces, but I'm quite certain that my heaving shoulders gave my secret away. By trying to hide my face, I only made things more awkward for them and ultimately Romeo scurried off with a freshly bruised ego (and possibly forehead) and MaryAllen was left strangely disappointed that her admirer had been too humiliated to leave his number.

I was brought to tears TWICE recounting this story, and it will forever live in my memory as my favorite dating disaster to date. Sorry, MA....

Dating Disasters

First of all, if you have not already checked out Dating Disasters at  

I'm writing this down, do so immediately. MaryAllen hysterically 

recounts her own experiences in the wild & wooly world of dating in 

New York City. She also shares the stories she's collected from readers 

and friends, so if you're single,read it for laughs and encouragement. 

If you're attached, read it and be thankful you've 

left all this madness behind you!

Most of my dating disasters have been insane over-the-top 

are-you-freaking-kidding-me type disasters, but hey, no one said 

this love stuff would be easy. I don't get upset when things

get awkward or horrible.... what's the point? I just try to learn from the 

experience and {eventually} laugh about it! 

The dating world can be pretty ugly, but I love that I can sit on the beach

during girls' weekend drinking Pirate Lemonade- I'll email that recipe 

upon request- laughing till my belly aches discussing the time in 

college when Ryan (aka Rico Suave) asked me to put a bonnet on 

him and highlight his hair. It was our second date. I refused.

Then there was the time I was set up on a blind date with a guy that seemed to have a great deal in common with me. He loved to travel, loved animals, enjoyed many of the same books and movies as me. The date seemed to be going great. We met at a pub famous for the gazillion beer options from around the world.. I'd like to point out that HE suggested this place. I was in heaven.. I love love love craft beers. Anyway, I suppose I was a little nervous because it when he first approached me he already had a beer in his hand and somehow along the way I forgot to check out what he was drinking. Yes, I'm one of those people who judge you by your drink... I know.. I know.. but at least I admit it. Anyway, about 3 rounds in, the waitress sets his beer down and this time the label catches my eye.

OK, so I'm not a booze hound or anything, but I enjoy a cocktail now and again and I take beer very seriously. I stared at him and pointed to his frosty beverage, dumbfounded. He shrugged and explained that he's a recovering alcoholic freshly out of rehab and going to meetings every day. UHHHHH what? Kudos on the recovery. God knows, alcoholism is a serious disease and I don't make jokes about it. But what the hell was he thinking asking me to meet him at a bar and then trying to hide the truth? I bid him adieu, paid my tab, and got the hell out of there. 

Perhaps the best of the worst was the time I was dating a guy we'll call Jacob. Jacob was a really sweet kind of artsy shy guy that I dated a few years ago. It was a long distance thing, and he invited me to his big night: the grand opening of his new restaurant. He'd been working for months to get everything ready and this particular night was an  invitation only, open bar kind of thing. I knew most of the night he'd be busy running things behind the scenes, but I'm a bit of a social butterfly so I had no problem mingling with strangers in a strange city for an evening. I love situations like that, so I was in my element.

I was having a great time, actually, until he showed up out of nowhere to introduce me to his mother and stepfather. Gulp. Ok as if meeting the parents isn't scary enough, he gave me no warning! She grabs me by the hand and drags me to the bar and starts ordering drinks. Jacob disappears. Before I can say Cosmopolitan, Mommy Dearest is 3 sheets to the wind. I try to gracefully bow out of our one-sided slurred conversation, but her grip only tightened. Literally... I had claw marks on my wrist. Things go from bad to worse in a hurry. Her husband ditched her as soon as he saw that she was occupied with me, so I literally had no way out. I swear I saw him smirking at me more than once. 

Sucker!

Finally she announces that she's got to find the ladies room. When I mentioned she was drunk, I mean she could barely stand. I liked Jacob, but I drew the line at helping his mother to the potty... even though I was aware that she physically couldn't get the job done herself. I knew it would involve a new level of inappropriate, and I just was not willing to go there. So I point her in the general direction of the ladies room and I hid in a corner, hoping to spot her husband so I could give him a heads up that she may need to go home. As I was breathing a sigh of relief and praying Jacob would be too busy to see his mother like this on his big night, I glanced over just in time to see her stumble into the kitchen. 

Oops. Crap.. crap.. crap... do I go after her? Where is her damn husband? Maybe if I tell a bartender or employee... crap! I panicked and do what I typically do in a panic: absolutely nothing. Suddenly she emerges out of the other kitchen door. With urine soaked pants. She staggers aimlessly for a few minutes and by some drunken miracle she spots me hiding behind a potted plant. The next thing I know, I'm the girl sitting next to the pee pants lady. 

I wish I could say these are all the stories I have, but why lie? It's all too much for one day. For more stories involving the tumultuous dating scene of the single and fabulous, don't forget to check out Dating Disasters. 

Or just watch this  classic Vince Vaughn clip from the movie Wedding Crashers to celebrate the awkwardness of things like "ass out hugs."