My First Date with Craigslist

A Cautionary Tale of Online Love and Lunatics


Published: November 8, 2007

Craigslist has everything from furniture to apartments to concert tickets up for sale. Since everything else is online nowadays and I was curious as to what dating was like in this forum, I figured there was no reason to not jump right into the online dating pool. For those of you courageous enough to brave the possibility of meeting a pedophile or a Dungeons & Dragons aficionado, here are a few useful tips that I picked up during my search for love on Craigslist.

1. Make this experience a group effort. I enlisted the help of my roommates Casey and Callie in my quest for “true love” online.  They not only added amusement to the ordeal by mocking the ridiculous ads with me, but helped me veto guys who were looking for a girl to urinate on or wanted to “make a financial arrangement” with an underage coed.  We finally settled on Pete, a filmmaker whose love of video games could be overlooked because he promised to make my roommates and I extras in the “Sex and the City” movie.

I also enlisted my friend Jon to follow me on my date with Pete.  I suggest reserving this role for someone whom you can blackmail with incredibly incriminating photos or whom you can convince that you may end up chopped up into tiny pieces in some techie’s refrigerator. Jon is neither; He’s just a good friend who followed us around the Upper West Side and sat at a nearby table in the café where I met my date, just so I wouldn’t be abducted.

2. Expect the unexpected. The people on the Craigslist dating classifieds are there for a reason.  Most likely, they are too weird to attract people in face-to-face interaction, so they resort to the Internet.  When I met up with Pete on the corner of 83rd and Amsterdam, I was expecting a 20-something hipster in skinny jeans with piercings. What I got was a 40-something man in a button-down and cargo shorts…with piercings. Failing to decode Craigslist lingo, I didn’t know that when an ad online says a man is “athletic,” this really means that he considers table hockey a sport. If it describes someone as “average,” it means this person has not left their couch in 12 years.

Also, be prepared for Craigslisters to bring up completely random topics.   Within the first five minutes of meeting me, Pete told me, in detail, about the plans he and his brother have for striking it rich.  They plan on starting a porn Web site, and he explained the gimmick that would set it apart from the rest by saying, “We know this guy that imports exotic animals, so in the background of every picture we’re going to have these exotic animals.  I think it’ll totally work.” I don’t know much about porn, but I’m pretty sure that some sick individual with an animal fetish thought of that one in 1996.

As if bringing up porn wasn’t enough, Pete thought that describing his friend Stacy’s lucrative job would add that special something to our date.  Apparently, she works in a seedy massage parlor, where a happy ending is one of their usual services. Pete seemed to think this was a solid business venture. At this point in our date, I realized that Pete was not The One.

3. Always be on your toes. These online daters question everything, so always be ready for your next answer if you’re lying. For example, I made up an excuse as to why I was texting (throughout our entire date) Jon directions to the café Pete and I were at. When Pete questioned my voracious typing, I wound up blurting out the first thing that came to mind.  “Sorry, my roommate doesn’t know how to administer medication to our cat, so I’m texting her instructions.”  Apparently, Pete considers himself a feline medical expert and began grilling me on the specifics of my cat’s illness. Flustered, I immediately began spouting more lies about my nonexistent cat. As far as he knows, I have a stray cat named Trixie who was recently diagnosed with diabetes.

4. Dress appropriately. Ladies, this means flats.  Gentlemen, this means sneakers.  Basically, you should dress as if you are about to run a 5k because you need to be ready to bolt at any time. I was thanking my lucky stars I had worn flats when Pete asked me to walk with him to his car (Who has a car in Manhattan, anyway?) and proceeded to offer me a ride home.  I figured his car was on my way home, so why not just put the cherry on top of the date and see what kind of wheels Pete has? We were walking toward a somewhat normal looking SUV, which I assumed he could afford on his filmmaker’s salary. Instead, Pete opened the door to what in New Jersey, we would call a “hooptie.” Pete’s classy ride can be described as a rusty 20-year-old car that has four different tires and one door that I’m relatively sure was stolen off a black Oldsmobile. Wearing flats enabled me to use the time that it took him to force open the duck taped door handle to make my quick exit, call over my shoulder, “Uhhhh, I’m actually going to walk! Had a really great time!  Bye!” and jog all the way back to McMahon.

5. Run home and change all of your contact information. Thanks to Pete, I decided that Craigslist dating is not for me.  Although I haven’t yet spoken to Pete since our lovely date, I plan on changing my e-mail address ASAP, just so he can’t get in touch with me again. If he does happen to get a hold of me, I’ll say I’m not dating right now because I’m in mourning for Trixie, who recently suffered a tragic death due to an insulin overdose.