Tag Archives: craigslist

The Bad Date Chronicles – 15 Second Man Edition

Gentleman...start your...oh..

Yes, the title means exactly what you think it does.  15 Second Man was the catalyst for this post.  Here is the rest of the sad, sad story.

15 Second Man was my 2nd (but sadly, not last) foray into the wilds of Craigslist.  There  was no picture attached but the ad was so charming I was willing to take a chance.  It was a send-up of the old Dr. Seuss One Fish, Two Fish book and consisted of about 20 really funny, thought-provoking questions.  Of course, possessed of a strong wit and a love of answering questions about myself (I have answered absolutely every question on OKCupid) I had to respond.  He seemed to really dig my answers and we exchanged numbers after some really entertaining emails.

Don't tell me you wouldn't hit that

Due to scheduling conflicts, we weren’t able to get that first date on the calendar for almost two weeks.  In the meantime, we had frequent communication, texting every day and talking on the phone almost every other day.  We sent photos of each other back and forth and to my surprise, he was attractive!  Definitely on the larger side but in a very cute, Man vs. Food kind of way.  Things got hot and heavy pretty fast.  The back-and-forth quickly devolved into full-on sexting and even phone sex, all before we had even met!  One day, we clocked in at almost 600 text messages sent back and forth.  Needless to say my productivity level at work plummeted. We were both almost drunk on anticipation of meeting each other, finally, in person.  Would the chemistry be there?

The night of the date finally arrived, and to this day, I can’t recall every being this nervous about a first date.  It felt like so much was riding on it, that I would be beyond embarrassed if this person, whom I’d already been pretty intimate with, would turn out to have no interest in me or vice versa once we actually shared the same space.  I was beyond relieved when I first caught a glimpse of him at the door of the restaurant.  He was adorable. And he seemed to think exactly the same of  me.  The butterflies and nerves quickly departed as we settled in at the table for some drinks and dinner, to be followed by a trip to the bowling alley.  The date couldn’t have been more perfect.  We were clearly digging each other, and having a great time.  When, a few hours later, he pulled me in for a kiss in the elevator of his building, I though I had died and gone to wherever it is that all good sluts go to when they die.

Despite the undeniable sexual chemistry, we actually “negotiated” what was allowed and not allowed once we got down to business.  We both agreed that we didn’t want to rush into sex, that we wanted to give it time for something to really develop before we took that step.  It was perfect!  All too perfect!  And then…I understood why he took the nuclear option off the table.

Cut to his bedroom.  We’re kissing.  Passionately.  Like in the movies.  And I don’t mean the kind you can get from Netflix.  Being the surgeon that he was, he was very, very, VERY good with his hands.  Being the feminist I am, I decided that he deserved some reciprocity.  The equipment was impressive.  Far from the smallest but not too far off from the biggest I’ve encountered and of a perfect girth.  I was literally chomping at the bit to get to work on this thing.

I’m no surgeon, but I’m pretty good with my hands as well.  I didn’t realize I was THAT good.  A mere 30 seconds after first contact, Old Faithful erupted unexpectedly and way ahead of schedule.  I was stunned – this had actually NEVER happened to me before, although I told him otherwise.  My years of high school theater served me exceedingly well that night.  I was kind and reassuring and all of those things you need to be in order to preserve the fragile male ego after is has suffered such a…blow.  Took my time saying goodbye and departed for the night with a very nice goodbye kiss. Continue reading


The Bad Date Chronicles – The Sexsomniac Edition

I met the Sexsomniac (nickname to be explained shortly) after seeing his ad and picture on the Craigslist “men seeking women” section.  Honestly, I was looking for a new place to live, but when I couldn’t find the 5-bedroom palace with swimming pool, sauna and butler for under $1500 a month I started getting bored.  I figured, if I could find a great deal on a race car bed (which I had) then why not a man?  Plus, it was free and I just didn’t have the motivation to pay for and reactivate my Match account.

If you’ve ever trolled Craigslist for a date, for anything really, you will be entertained and appalled in equal measure.  Some men come at you with humor (I once had sex for 1.5 hours.  Of course, an hour of that was spent crying.), descriptions of their..ahem..equipment, their barely concealed misogyny (Looking for a real girl, no drama no bullshit. Just be real) or their very specific requests (Searching for Asian woman. 5’1.5′ and under with no kids and a good sense of humor.  Oh and must love grapes).  Bad spelling, grammar and punctuation abound.  You really don’t go on Craigslist hoping to find the man of your dreams, but if you’re just looking for a date, it’s really not much worse than any other way. Bad dates come in many forms, and they issue forth from many dark corners of the internet.
After being genuinely stunned, frightened and vaguely sad for humanity in general, I stumbled upon the Sexsomniac’s ad.  It was very unassuming, almost Puritan in its simplicity.  “Hi, my name is “Seymour” and I’m 30 years old.  I am in the process of finishing my law degree and am looking for a great girl to meet and see where it goes from there.  I’m 5’10” and 160 pounds.  Hope to hear from you!”  Ok, not terribly witty or outstanding or even remotely interesting but there was a picture attached and I couldn’t deny that he was an attractive fellow.  I decided to take a chance on it being a) a really, really old picture or b) a picture of someone else.  I replied to the ad, attached some pictures and was mildly surprised when, less than a day later, I received a reply. We corresponded for a day or two, and the emails were succinct, witty and I was impressed by his grasp of the English language in general.  I gave him my cell phone number and was delighted to receive a text message, asking me when was a good time to call later that evening.
The appointed hour came, and right on time I received a call. We must have spoken for a little over an hour and had a very spirited and intellectually stimulating conversation about politics, relationships, world events, etc.  There were lots of laughs, a dozen little delightful coincidences and absolutely no awkward silences.  So when the time came for us to hang up, I was more than willing to accept his invitation to have a drink later on in the week.  A day or two passed and he texted back to confirm our date, along with the time and the place that he had picked out. I immediately took to Yelp to check out this place, and it was adorable!  Patio with twinkly lights, great beer menu, right outside of the BART station so that I wouldn’t have to walk very far to get there.
I couldn’t remember the last time I had been this excited for a first date, and I put on my favorite date outfit and paid extra attention to my hair and makeup.  In short, I looked amazing!  I got to the bar a bit early and scoped out a seat on the patio, contemplating whether or not I should pre-game the date since I was starting to get a bit nervous.  Before I could do that, he arrived, looking better than his picture and smiling in a way that made his eyes crinkle up in the most adorable way.  My heart gave a little lurch as I stood up to hug him hello.  We made our way inside and got a couple of beers and then headed up to the second floor to find a nice quiet table.  Things seemed to be going very well.  The beer was great, the company was even better and we were getting along wonderfully.
About 15 minutes in, he leaned in and let me know that he had to tell me something.  And…here we go I say to myself.  The deep dark secret, the dealbreaker that everyone has was about to be revealed to me right here on the first date.  Trying to conceal my disappointment, I leaned in.  He tells me that he has a condition in which he performs sexual acts on whoever he happens to be in bed with in the middle of the night.  The next morning, he doesn’t remember doing it.  In essence he’s sleepwalking.  But instead of walking in his sleep, he’s fucking in his sleep.  The condition is called, I kid you not, Sexsomnia.  Lucky for him, I watch 20/20 and 48 hours so I have actually heard of this condition and to be honest, I’m a bit relieved that this is the big secret, and that it’s out.  Am I thrilled about it?  No, not exactly but I’m not completely horrified.  I make a mental note to never sleep over, but at this point there’s still too much promise to pull the fake “my cat is on fire” phone call.  All that was about to change however. Continue reading