Sunday, September 7, 2008

In Which I Suck at First Dates

The guest writer for today's post is the only male reader that I know I have, as of recently anyways. Aaron at Daddy Files is very expressive, and is unafraid to talk about how much he loves his wife and son, and has a penchant for MILF's.


When it comes to talking to women and making solid first impressions, I’m about as successful as Sarah Palin teaching abstinence to her daughter.

It started back in high school shortly after I earned my driver’s license. I was kind of shy back then and girls liked me, but only as a friend. And since all of my friends were captains of the football, baseball, soccer and basketball teams, they got all the women and I actually had to find a date at another high school where no one knew me.

I lucked out and got a date through a friend with a cute redhead named Terri. So there I am, 16 years old, sitting with my blind date at Friendly’s and finding it really hard to say or do anything cool. Then I watched in frozen horror as some older guy checked out my date, walked right over to the table and gave her his phone number telling her to call him when she “ditched the loser she was with.” I should’ve at least told the guy off, but I was a big wuss at the time and did nothing.

But despite that, she was still interested. So off we go to the car and I ask her what she wants to do next since it’s getting kind of late. She tells me we can “just sit in the car together for awhile.” To a guy with any kind of game, that would’ve caused alarm bells to ring but for me…nothing. Totally clueless as I sit there not even trying to kiss her.

Sensing my complete lack of common sense, she decides to make it abundantly clear that she wants to make out with me. She asks me if I want to see the hill she trains on for track. I find this to be a little odd, but I go along with it. As we pull into a completely empty parking lot with no lights at all, Terri says “Oooops, I forgot it’s nighttime and you can’t see the hill” as she leans toward me.

Now you’re probably thinking to yourself “even he can’t screw this one up right?” Well my friends, you’d be wrong. I turned to her and said “Oh well that’s OK, we can see it some other time. Where do you want to go now?”

If you think that’s bad, you should’ve seen me the next day relaying all of this to my friends who nearly killed me for being so dumb.

I’d like to say it got better as I got older but that’s just not true.

I remember the first date I went on after I had my heart broken by my girlfriend in college. She had broken up with me just before she went to live in New York City for the summer to pursue her acting career. We didn’t talk much during that time, and if we did I probably would’ve been a little more prepared for what happened one summer day in 2001.

I’m sitting at work when my phone rings and one of my friends is breathless with excitement telling me to turn on MTV “RIGHT NOW!” So I turn it on and that show “Wannabe” is on. Do you remember it? Where three contestants try to talk, dance and sing like a famous artist? Well wouldn’t you know it, there’s my ex-girlfriend on TV trying to become the next Kylie Minogue. Barely dressed, she’s strutting around stage like a glorified stripper and she actually won! And let me tell you something…there’s hell, there’s burning hell and then there’s seeing your ex on MTV half naked for the world to see.

So anyways, I went on a date with a girl shortly after that in an effort to get her out of my system. During our dinner, we start talking about our likes, dislikes, musical tastes and what we watch on TV. She casually mentions she’s a huge MTV fan and before I could even think about keeping my stupid mouth shut, I say “MTV? I fucking hate MTV!”

Needless to say it caught her by surprise so I had to explain everything. And as you all know, there’s nothing like talking about your recent ex on a first date.

But there’s no better first date story than the one I went on in 2004 with this cute girl. Things were actually going really well and for once I was on my game. No talk of ex girlfriends, no missing obvious signs…I was in the zone.

I even got her back to her place where we were getting closer and closer on the couch. As it turned out, we had some common acquaintances and we both shared a vehement hatred of a girl named Kelly. And since things were going so well and I was sure we could bond over our mutual dislike for the girl, I began to tell her a story.

I told her all about how Kelly was drunk at a party one time and we had her on videotape talking about what a huge whore she is. Kelly was drunk and talking about her ex-boyfriend’s huge member and how she liked it when she “did him up the ass.”

Well at that point my date’s face turns completely white. Fearing I’ve overstepped my boundaries, I backpedal furiously and ask if I’ve offended her with that kind of language. She shakes her head no, but still looks upset. I desperately ask her to tell me what I’ve done wrong so I can fix it. Then she turned to me and said:

“Kelly used to date my brother. She was talking about him.”

I feverishly thought of something I could say to remedy the situation, but came up very, very empty. So I just sat back and said “Sorry, but I just need a little status check here. We’re on our first date, things were going well and then I just inadvertently brought up your brother’s huge dick in conversation?”

This stuff only happens to me, I tell ya. But maybe it wasn’t all bad, because my date that night is my wife now and her well endowed sibling is now my brother-in-law. We all have a good laugh about it now but I consider myself very lucky that I have no more first dates in my future!


Lola said...

Did you ever ask the BIL if Kelly "did him up the ass"? I know I would have.

I don't think anyone is very good at first dates. If a guy was a great first date, I'd be suspicious of him. He's obviously had too much practice!

Great post, Aaron!

Kim said...

Oh, don't worry.

Sounds like you've kept your touch.

Your joke about Sarah Palin's daughter shows you know how to keep it classy still.


Daddy Files said...

If you can't joke about teenage pregnancy I don't know what you can joke about.

And I don't recall EVER claiming to be classy.

It's a joke, lighten up...

Lola said...


Heather said...

OMG I wasn't expecting that to be your wife. And I remember Friendly's! Never got to eat at one, but wanted to really badly for some reason.

Moonspun said...

Daddy Files, nice post! I was hoping as I was reading it and the tension mounting that at some point you'd describe your first date with your wife.

patty said...

Huh. I thought every meal at Friendly's concluded with a happy ending.

Daddy Files said...

Touche Patty...touche!

But unfortunately only my "massages" end that way!

Employee No. 3699 said...

So yeah, did you ever ask your BIL if Kelly did him up the ass?

Daddy Files said...

Sorry, sorry...I guess that's how mistakes are made and reputations are ruined huh?

One little pronoun error and the wrong person is getting it in the pooper! To officially clarify my error, it was supposed to read HE did HER up the ass.

I apologize for the anal confusion.

Lola said...

Dude, that changes EVERYTHING! Are you just covering now? Come on.

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