A summer fling is clearly not a click away

By Leila Sales

Look out: The summer is closing in upon us! Sure, it may seem impossibly far away, but I promise you, the next six weeks will fly by, so we need to make our summer plans now. We need to find summer jobs and summer sublets, and, above all else, we need to find summer boyfriends.

And not just any men will do. Personally, I plan to acquire an extremely wealthy summer boyfriend, one who always wears topsiders and madras shorts, and who has a swimming pool in his backyard. We will spend every day lounging in this pool while his foreign-born staff plies us with tequila sunrises. Every once in a while, he will turn to me and say, “Darling, put on some clothes—let’s go for a ride!” Then I will throw a Lilly Pulitzer sundress over my bikini, and we will hop into his convertible and go cruising around town while laughing debonairly in the manner of very, very wealthy people.

I have intended to do this every summer since I was 15 years old. Why it has not yet happened is a mystery to me.

Clearly, the only people wealthy enough to fulfill my dream will be creepy older men who discover that their standard summer pastime of golf at the country club no longer entertains them. That’s why they need new summer hobbies, i.e. girls who are half their age.

There are two places to find creepy older men: dimly lit bars with names like “The Hideout” with bartenders who wear low-cut shirts and whose eyes indicate that they are dead inside, and Craigslist.com. One of these involves leaving the house, and the other does not. You can imagine which method I chose.

To find my special someone, I posted a personal ad on the “women seeking men” section of Craigslist. It read as follows:

“About You: Spending the summer in Chicago, looking for a hot summer fling. Must have convertible for trips to the beach. Must be tall and relatively handsome (the nicer the car you have, the less it matters!). Must enjoy tennis (let’s play doubles!), sailing, and sex (let’s play doubles!). Bonus: love of music and/or the arts.

About Me: I am 5’7” with blue eyes and long, dark curls. I recently graduated from college as a French major, and I’m looking for some last-minute fun before I move to Provence to begin my new career. I’m looking for the right man to sweep me off my feet this summer.


I wait with bated breath to see what hot studs will reply to my enticing personal advertisement. Three minutes later, I receive my first e-mail. It’s from “Jesse,” who writes, “You are such a dumb gold-digging whore.”

I am momentarily offended, until I remind myself that my posting was filled with lies: I’m not a French major. And I’m not 5’7”. Therefore, I am not a gold-digging whore. This mollifies me, though I am baffled as to why someone would go out of his way to inform a stranger on Craigslist that she is a whore. Doesn’t he have better things to do? Like, I don’t know, make out with a girlfriend? No? (Oh, snap.)

Other interesting responses include “CJ,” who writes, simply, “hey babe.” Oh, yes, “CJ.” Good. You have won me over now.

Or then there’s “David” and “Scott,” who both write long descriptions of their various hobbies, physical attributes, and sexual proclivities. Very interesting, boys, but do you have convertibles, or do you just copy and paste the same e-mails to every vaguely coherent Craigslist posting?

And let’s not forget “Jason,” who tells me I seem compelling and beautiful in my posting. I take this as a well deserved compliment, momentarily ignoring the blatant falsehoods on which I based my ad. (I can’t play tennis. And I can’t sail. And my “long, dark curls” really aren’t so much curly as they are wavy.) I decide that “Jason” has real insight into my character.

If I had to pick a winner out of this lot, I’d go with “Matthew,” who writes nothing but sends photos of his car. Clearly, this man read my ad with an eye for detail.

Nobody who replies to my posting addresses any of the key issues, such as, “What do you mean, ‘love of music and/or the arts’? What music? What arts? Any? Can I love Marc Anthony? Does that count?”

Or, “What the hell kind of career are you pursuing in Provence? Wine-making?”

Or, “‘Let’s play doubles’? What does that mean? I do not understand one single word that you just wrote.”

I draw a few conclusions from my foray into the wild world of Internet courtship. One, everyone on Craigslist makes me feel sad. Two, I should do more of this sort of “investigative journalism” which doesn’t involve leaving my desk. And three, if I really want to spend my summer cruising in a convertible, I may have to buy my own.