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The Honest First Date

August 27, 2019
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Blog
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Posted by Geoff Woliner

 

 

Jon: Jane…right? Hi! I was somewhat excited to meet you tonight, because it was either this or do my taxes, so I figured, what the hell?

 

Jane: Me too! And for the record, you’re significantly older and more rotund than your profile pic led me to believe. And a clear downgrade from my last boyfriend who I’m still not over and will be talking about at great lengths this evening.

 

Jon: Great, I’ll make a mental note to feign interest during that segment.

 

Jane: I’d appreciate that. And I’ll also be discussing several other topics of little to no interest to you, including my cat, the bitches I hate at work and the strained relationship I have with my sister who’s been in and out of rehab for the past year.

 

Jon: No problem, that’s par for the course. I’ll simply smile, nod, and ask the occasional question as a way to convince you I’m paying attention. Just know that this is all part of a well-crafted strategy to take you back to my apartment and subsequently never contact you again.

 

Jane: I appreciate you paying your dues as part of this ritual, so I can convince myself you’re a decent guy and alleviate any guilt I may have about getting intimate with a complete stranger whom I know nothing about. And speaking of pay, I presume dinner and drinks will be on you?

 

Jon: Of course. I’ll whip out the platinum card to make you think I’m a big deal, and cross my fingers that I’m not over my limit yet again. If you knew the true, horrid state of my financial situation, it would make you question the very existence of God.

 

Jane: Excellent. And speaking of which, I’ll expect you to outline your long-term prospects in very granular detail, and make it all sound compelling. I need to convince myself, my mother and my friends that this isn’t an extravagant waste of my time, and that I’m still able to attract men of value. 

 

Jon: That won’t be a problem. Along with the other multitude of lies I plan on telling tonight about my high school sports career, past relationships and general philosophy on life, you won’t even notice that I can’t locate Gambia on a map when I talk about my plans to build a solar plant there.

 

Jane: Sounds great. I also intend to partake in the time-honored ritual of pretending to eat less than I normally do. Frankly, I wolf down pizzas and hoagies in ways that would put your college buddies to shame, but if I feel like a lady, it would go a long way towards helping you accomplish your nefarious goals at the end of the evening.

 

Jon: Duly noted. And when I order my fifth Manhattan and give you the, “I don’t normally drink this much” routine, rest assured that I normally drink significantly more. If you knew the extent of my functional alcoholism, your friends would have frantically talked you out of this rendezvous.

 

Jane: That’s ok. There’s a better than 50/50 chance that I’ll trash you to my friends after this encounter as is. I’ll nitpick every detail, including your hair, shoes, wardrobe and the way you chew.

 

Jon: Rest assured, if I remember your name, which is a dicey proposition at best, then a reciprocal character assassination will be in the cards.

 

Jane: That’s fair. And also brace yourself for my phone being the third wheel on this date, as I clearly prioritize texts and Facebook notifications over your heartfelt rendition of your brother’s life-altering car accident.

 

Jon: Deal. I’m looking forward to the following four hours that will have the ease and comfort of a root canal.

 

Jane: Me too, and good luck tonight! I hope you put on a good enough show to get what you want.

 

Jon: Thanks Jane, you’ll get my very best half-assed effort.

____________________________________________________________________________

Winning Wit, winner of Wedding Wire’s “Couple’s Choice” awards, is a team of award-winning comedians who help people write and deliver dynamic speeches and presentations through the application of stand-up comedy techniques.

 

Winning Wit has been featured on WTOP Radio and in several event publications as the leaders in event speech writing and coaching.

 

Do you have a big speech, presentation or other big life moment coming up? Contact us today, and we’ll see how we can make a star out of you yet.

 

Or at least make sure you don’t suck.

 

Twitter: @WinningWit

 

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