The Over-prepared Sleepover

The first meeting with Jessica was going much better than expected.

Then again, given the low expectations Mike had set for the evening, how could the night not exceed them? This was, after all, a group blind date, which in most cases are variably described as “unmitigated disasters.”

Group Blind Dates are defined as a meeting that occurs between two people whom have never met before, but in an effort to avoid the awkwardness of being totally alone with a relative stranger, each party brings a friend or two to soften the conversation load. This way, if the girl bears a stronger resemblance to Katherine Hepburn in On Golden Pond instead of Katherine Heigl in Knocked Up, they can easily escape a painful meal alone together.

Mike always prided himself on being prepared ever since he was a top Boy Scout in his pre-teen years. And when it came to his blind date with Jessica, he ensured he had other options ready in case things, or her, got ugly.

Call it a blind date…with a safety net.

This GBD was different, however. The conversation between Mike and Jessica became a three-hour run-on sentence….like the way one of those annoying couples in those ubiquitous eHarmony commercials explains their first encounter. Yup, they got along as if they were old friends, leading to more drinks, barhopping, ditching their other friends, and eventually for Mike, to Jessica’s bedroom.

As they rolled around in the drunken, sloppy throes of foreplay, Jess breathlessly uttered her conundrum, “You’re driving me crazy (inaudible sound)…and I want to have sex with you (inaudible sound)…but…”

Mike, pleased that his fingers could do the walking so effectively, answered with the perfunctory question:

“Are you sure?”

“Yes, but here’s the problem,” Jessica answered as she kissed/sucked the skin off of his neck (I’m starting to write like Jackie Collins, but bear with me). “If we have sex now, I can’t date you. But if we don’t have sex, we can still see each other.”

Mike was understandably confused by her thought process but attempted to give his interpretation anyway. “So if we have sex now, then we can’t build a relationship off of that. But if we do, then we’ll never be able see each other again in a dating capacity.”

Jessica stopped and looked at him, “Exactly.”

He agreed to option A, only because he just got laid a few days ago by an ex-ex-girlfriend and therefore wasn’t chomping at the bit to get something, anything, in this capacity. Jessica, pleased at the choice Mike made, then did her very best to get his mind off a short-term effect of blue balls. Kept the change, too…

Mike and Jessica agreed to see each other again the following Tuesday. After a nice dinner and a few drinks, he dropped her off in front of her apartment with a strange uncertainty as to whether he would get invited in again.

“I had fun,” Jessica said as she leaned over to kiss him goodnight. “Maybe we can see each other again this weekend.”

“Sounds good,” Mike replied. “I’ll call you later in the week.”

And that was that. As he drove away in a Travel taxi, he already began to look forward to their next encounter.

“She played the good girl tonight to redefine the relationship,” he thought to himself. “I’m sure things will change this weekend.”

Friday came with an email invite from Jessica to watch “Desperate Housewives” on Sunday night at her place. Mike responded by offering to bring take-out food over around 8:00. The itinerary in his mind was already laid out:

8:00 PM: Eat 9:00 PM: Desperate Housewives 9:30 PM: Not-so-desperate sex with Jessica Home by 11:30…

At 7:55 Sunday night, Mike picked up the food and was approaching her apartment when he suddenly realized that he had zero protection on his person (his most recent ex-girlfriend was on the pill). In a rush, he purchased a box of condoms at a local bodega. In his haste, he threw them in the bag with the food.

After he knocked on her door, he suddenly realized where Trojan Man was. She won’t be too thrilled with ribbed condoms as the appetizer, he thought, but as he reached to get them out, the door swung open.

“Helllooo,” said sang, giving him a hug. “I am starving, let’s eat!”

Mike clutched the bag. “Oh yeah, me too!”

He then asked the only question he could think of:

“Hey, can I use your bathroom? I drank a ton of water today after I went to the gym and have the bladder of an old man.”

“Sure, I think you know where it is,” she smiled. Mike proceeded to quickly walk into the bathroom without letting go of his precious cargo. Upon shutting the door, he took the condoms out and placed them under the sink, all the way in the back behind several bars of soap.

Relieved, he walked back into the kitchen.

“Do you always take food into the bathroom?” she asked.

Acting surprised, Mike laughed and said, “I always do that with the remote control. I just forget what I’m holding in my hand sometimes.”

Jessica looked at him a bit puzzled but shrugged it off as a typical “guy thing.” They proceeded to have a conventional couples’ Sunday night: Dinner, TV, and off to bed when she asked him for a massage.

The back rub for her soon became a front rub for him. Mike kept wondering when she would ask if he “had anything on him” in terms of protection, but the question never came. Instead, Mike was treated to another edition of Jessica’s rather complex way of thinking.

“I used to be more liberal about sex,” she offered. “But now I’m much more selective. It will probably be awhile before we do it. I hope that’s OK.”

“Sure…that’s fine,” Mike responded softly, stroking her hair. “That stuff doesn’t matter much to me, anyway.”

Mike was feeling quite blue when he left the apartment an hour later.

A few nights later, a call came in from you-know-who. She didn’t bother to say hello.

“So, did you leave ANYTHING at my apartment on Sunday?” It was more of a demand than a question.

Mike, knowing exactly what she meant, tried to sprinkle some humor into the awkward conversation: “I guess you needed some more soap.”

“Uh, yeah,” she replied. “So I guess you assumed you were going to get laid last Sunday.”

“That was the assumption, yes,” Mike sheepishly replied.

“That’s a pretty ballsy assumption,” she said. “You know we’re not going to have sex.”

“Well, we almost did on our first date, so the expectation was set,” he carefully explained as if he were a therapist. “Usually when people almost do it early on they invariably go all the way when placed in the same situation again if it’s a short time after, so I got a box on my way over.”

“One condom is responsible. A whole box is an insult,” she shot back. It was a line right out of “Dawson’s Creek.”

“True…” he said, out of answers.

Jessica was silent for a moment. “Well, I spoke to one friend, Michele, about this and she agrees with you.”

“Come again?” Mike asked.

“But my other two friends said I should never speak to you again.”


“Michele sees you as being responsible for taking the necessary precautions. She thinks you had every reason to believe we were going to have sex.”

“And Michele is a very pragmatic, wise individual,” he declared.

“Don’t get cocky,” Jessica replied. “While I now agree with her, it doesn’t mean you’re completely exonerated. You could have told me about it that night.”

Mike agreed (he would have agreed to move to Lodi if it meant ending the conversation). And Jess agreed to see Mike again. But there was a new scent in the air: One of slight mistrust and false expectations. Mike realized that she was never going to have sex with him until their wedding day, if for no other reason than to make a point.   Mike in his pre-puberty years   Two weeks later, the emails and phone calls between the two diminished. The reason was simple: The moment the IDEA of someone you are dating is altered negatively the relationship has no chance. Sometimes the idea of a person is a stronger attraction than the person him/herself.

In this case, Mike, through acting responsibly, went from a nice guy with good intentions, to a myopic, clumsily responsible guy with one thing in mind. z

Following the Boy Scout motto of “Always be prepared” can sometimes backfire, or in this case, not fire at all.

Because when it comes to women and how they’ll react, one can never fully be prepared.