Life of Cyn: Uptown girl meets downtown man


Dear Cyn,

Most weekends my girlfriends and I like to hang out at the CC Club or Liquor Lyle’s, but last weekend for a laugh we got dressed up and went out to The Drink. We had a blast, and I ended up dancing with this really hot guy. He was very well-dressed in an expensive three-piece suit, and he said he works downtown at an investment bank. He gave me his number and I can’t wait to call him, but I’m worried about what will happen if he finds out that I’m not really the little-black-dress-and-heels type. Should I ask him to meet me at the W Hotel…or should I take a chance and suggest Matt’s Bar? What if he gets Juicy-Lucy juice all over his Brooks Brothers shirt?

Uptown Girl

Dear Uptown Girl,

It’s always fun role-playing, and even more fun when you attract a hot guy in the process (who may, by the way, be role-playing too. Did you actually get a card?). It’s hard to go wrong here. Just like you, he may have been posing as a sharp dresser too! Or, he may be interested in slumming, e.g. hitting Matt’s or the C.C. What guy doesn’t like Juicy Lucys, cheap beer, and shooting pool, especially in places that the ‘Mats and Soul Asylum guys hung out at? And this early in the game, there’s no telling what he likes—millionaires have been known to hang out at dive bars like Palmer’s and Lyle’s. If he isn’t into your scene, would you want a relationship where you have to wear nylons and uncomfortable shoes everywhere you go? How much do you really want to make The Drink your new hangout space? On the other hand, if you’re just interested in a steamy one-night “relationship,” you could ask him to meet you at the W Hotel, and play the role of Downtown Girl to the hilt!

In response to your last question, if he gets Juicy-Lucy juice all over his Brooks Brothers shirt (or if you “accidently” spill your drink on it), it’s is the perfect opportunity to offer to take him home and take off his shirt to wash right away. Trust me, this works.


P.S.: Remember, keep it loose. You never know when he might ask for a bailout.

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