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Valentine’s Day Hangover

By The Second City | Feb 15, 2013

In honor of our nation’s most disposable holiday, Second City actress and love guru, Eileen  Montelione, has been generous enough to give you guys out there a tutorial on how to fuck up a first date. Or in her case, how to win over her heart. Happy V Day!!!


1)  Show up in Crocs. With socks.

2) Tell her she reminds you of a younger version of your more attractive daughter…who is by   the way, “no longer with us”.

3) Make sure as you drive you say that every consecutive song on the radio is your favorite song.

4) Stalk her for a week before the date, so you know what to talk about.

5) Then, get drunk, flirt with the waitress, and hint (very obviously) that your date is interested in a threesome, but is too shy to ask.

6) After she orders, say, “Carbo-loading for the marathon, I see.”

7) Breathe in and out solely through your mouth.

8)  Take her by the hand, stare deeply in her eyes and tell her you took one look at her profile pic, and decided to leave the condoms at home because you can just tell she’s a “Strictly Anal” type of person too.

9) If the for some reason the date still goes well, when you bid goodnight, whisper in her ear, “How much do I owe ya?”



Eileen Montelione  is sick and tired of world hunger, prejudice, and consistently getting her best ideas the second her head hits the pillow at night. Sadly, her undying sardonicism will forever discourage her from any attempt to do anything about anything. She shares a birthday with Bruce Vilanch, who is one of her heroes (other heroes: Trey Parker, Matt Stone, and everyone involved with Arrested Development).
Follow on Twitter: @emonte3


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