FUNNY WOMEN #115: Craigslist Formal Encounters


If you enjoy both giving and receiving, then I guarantee you that you will not be disappointed. Beautiful Connecticut goddess seeks well-endowed man for National Endowment of the Arts Benefit Gala. Must host (after party at Sardi’s).

Do you enjoy the finer things in life? Maybe we can enjoy them together. Sophisticated businessman would like a classy companion for upcoming New York Philharmonic series. I’m open to any and all potential matches, as long as you’re a freaky Latin dominatrix whose name begins with X, J, or D (no Deborahs).

Gentleman randy for high culture interested in encounter at the opera with discreet female. Let us sit in the dark together and partake in a sexy live show. Arias and outcalls only.

You’re a single guy or girl below 79th Street on the Upper West Side. We’ve been married 15 years and are looking for someone with whom we can spend some quality time. Do you like watching the human body pushed to incredible limits? Then give us a call. Attractive, outgoing couple seeks third for adventurous evening at the ballet. Must be fit, clean, and interested in Sleeping Beauty.


Mature woman seeks a man who can handle her AND another woman. In my dream scenario, you’re smart, kind, and financially secure; she’s a pretty stranger I will arrange for you to meet in a coffee shop and sweep off her feet. If you’re the one to fulfill this fantasy, then please contact me, your future mother-in-law, so I can pass on Laura’s number. I’m happy to host (you for all major holidays). No vegans.

I’m tired of wild horses. Help me fill my needs and I’m sure we can make it mutually beneficial. Wealthy man seeks well-hung stud for an unbridled weekend of mating with my thoroughbred mare. Please send pics.

Are you a stylish woman with a sense of humor who gets off on watching degradation? Then please join me for a night you won’t forget at the White House Correspondents’ Dinner. Please—no weirdos or Republicans.

Are there any good women out there waiting for Prince Charming? Horny white male seeking petite companion for sexy spring wedding, followed by no-strings-attached lifetime together. 421 (champagne) friendly.


I’m a sexy, fit woman in need of a partner. Looking for an athletic man who’s not afraid to work up a sweat. If you can rise to the occasion, then let’s play together this weekend, at The Hamptons Mixed Doubles Tennis Tournament. Would love to dominate.

I need a party girl with experience handling virgins. If this is you, then I’m willing to make it financially attractive for you to plan my son Morty’s Bar Mitzvah at the Plaza. Interested in dinner and perhaps more. Please send pics! (of past events in and around the Manhattan area).

Submissive male seeks company of BBW. If you’re up for the ultimate oral pleasure, then please join me for an evening of Garrison Keiler at the Beacon Theatre.


Rumpus original art by Annie Daly.


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After graduating high school as the class valedictorian, Rupinder Gill studied Arts at the University of Toronto then moved back into her parents’ basement for a year. Her first book, the best-selling On The Outside Looking Indian, was short­listed for the Stephen Leacock Medal for humor writing. Named one of Canada's funniest female writers by CBC Book Club, she has also written for the NBC/Global comedy Working the Engels, The Onion, O Magazine, McSweeneys, CBC Radio, and This Hour Has 22 Minutes. More from this author →