It is no secret that I love, love, love reading Craigslist’s treasure trove of awkwardness, the Missed Connections section. So, of course, as we all continue from a weekend filled with makeup, witches’ brew and masked make-out sessions, I couldn’t resist an opportunity to round-up some of my favorite Chicago MC’s to tell a little tale of Halloween lure (in addition to sharing some tunes).

Personally, Halloween has never been a holiday I associate with wild hook-ups, but maybe that’s because my costumes are usually not of the “Sexy (Fill-in-the-Blank)” variety. I’m usually in drag, covered in grotesque makeup with stubble poking through, and this year was no exception as I took on the role of Little Edie Beale from Grey Gardens. The below characters seem to have had some good luck knocking boots, even if they had a lot of explaining to do for their mother upon their return home. Here’s hoping the fates bring these lovers back together.

Missed my chance with Mr. Franzia – m4m (Belmont/Monroe)
Date: 2009-11-01, 11:33PM CST

“I had black paint smeared on my face. I admired the intricacy of your costume: Franzia boxed wine. We made some contact on the train before both getting off at Monroe. There we kissed at a street corner, where a passing driver yelled “FAGS!” at us (just in case you didn’t notice) … Sorry for not following, but, in all honesty, I was staying with my mom (who was visiting) in a hotel. That being said, I’d love to hear from you and maybe engage in some out-of-the-box conversation.”

ms wonderland left wondering? – w4m – 20 (in tinley)
Date: 2009-11-02, 2:40AM CST

“ok so i went 2 a halloween party with a gf and i was the sexy ms. wonderland girl. i was soooooooooooo wasted n u were so much fun and we ended up being naughty but i don’t remember most of it lol. u had on a dark costume not sure what it was though dah? well i have a bf so i guess it had 2 b a one time thing, just wanted 2 say if u ever read this i was the small blond who u helped have a really fun halloween!”

The outlaw Josey Wales – m4m (near loop)
Date: 2009-11-01, 6:47PM CST

“To the outlaw Josey Wales: it was so hot to watch you polishing your gun. A nice long gun, with a big thick barrel and a nice head to it. I can still taste that ammunition dripping into my mouth.”

Of course, since these are Missed Connections, after all, not all of these rendezvous were as successful. Lesson be learned: Be sure to carefully stow your beloved university-provided metro card when going home with handsome men in “dark costumes.”

Halloween Party then Your Apt – w4m (lincoln park area)
Date: 2009-11-02, 10:28AM CST

“Friday I was beligerent, I apologize. I dont remember practically anything when we got to your apt, let alone how we did till my friend filled me in. Uhh yah I lost my Upass at your place did you find it??? That would bloow if I have to find another one. Ps. “my buldge” seeing I was spider man is in your room too, white/pink soccer socks? Yeah, well I’m sorry for being a slob, im sure i was a huge one. But on the bright side I do think your adorable!”

Georgia at Halloween Church Party – m4w
Date: 2009-11-02, 5:15PM CST

“I was the Chaplin with whom you danced. I got swept up into an evening of events that now seem unreal. If you find this, please shoot me an email. I’d love to see you again and take you dancing.
Take Care

A Somewhat Silent Man”

oh, pinnochio – m4w (subterranean)
Date: 2009-11-01, 11:24AM CST

“that little boy look didn’t fool me, you were smoking hot. i never made it to the hideout, but i did spend a more than a few minutes thinking about what it would be like giving it to a puppet that wants to be a real boy, but is actually the hottest little girl in the room.”

But, I think the most important lesson from all of this is to watch out for each other. Halloween is a time for all of us to come together and bask in the ridiculousness of it all. And protect each other from violent religious leaders. Especially if you’re dressed as a pop diva.

Kid that got hit by the pope at Evil Olive – w4m – 21 (Evil Olive)
Date: 2009-11-01, 9:19AM CST

“Lady GaGa wants to make sure you’re ok.”