“Jess” was one of the many women I would come to meet during my dating experiences that fell into the category of ‘Perfect on Paper’.  The problem with each and every one of these PoP dates so far was that I just wasn’t that into them.  They all had a lot going for them and I just wasn’t feeling it.  Some would take longer than others for me to figure this out, but I did figure it out with all of them in the end.  Jess was a little different because I genuinely felt bad about how our dating relationship ended.  I wasn’t proud of what I had done, but I did learn a valuable lesson – one that I vowed to never repeat again.

“Hot to Trot” – Tales of the Wham, Bam, Thank You Ma’am

Fear Factor: 2
What-the-hell-just-happened? Factor: 2
Good Riddance Factor: 3
Crazy Factor: 5

The Date Setup

Photo: by antwerpenR via Flickr

Jess was the one of the very (very) few people I ever met from a posting I made on Craig’s List.  Ugh…I know.  Craig’s List.  It makes me cringe at the thought of even mentioning it.  I’m almost embarrassed.  Of course, when I posted my ad on CL, it was at least somewhat viable as a means of finding love.  Today it seems that Craig’s List isn’t worth the bandwidth it’s served up on for the purpose of finding love (or anything other than a casual encounter or a friggin’ couch).  I wanted to try every possible angle I could, so I gave it a shot.  The vast majority of the replies I received were from women that I had absolutely no interest in meeting, let alone dating.  I even received a few replies from men (yes, men) that were hoping I’d be “open minded” enough to give them a try.  After all, when you close your eyes you can’t tell the difference as they explained.  Yeah, I puked in my mouth a little as well.  Jess was the first real quality woman that replied to my ad, and after the previous replies I received, she was angelic in comparison.  She was a single mom, had a great career and lived fairly close to me.  What more could one want?  We emailed a bit and then decided to meet up for coffee.

The Date Plan

The coffee date went well – well enough to warrant a second date, but nothing that blew me away.  I wasn’t looking or expecting to be blown away on the first date.  I know that sometimes people take a while to warm up.  Nerves are involved, people can be shy and first dates certainly have their intimidation factor.  I tried to take all of this into account.  We talked fairly frequently – as often as our busy schedules would allow and ended up going out a few times. Again, the theme of the dates thus far was simply blah.  I SHOULD like this girl.  Why wasn’t I into her?  I just couldn’t put my finger on it.Our date was coming to its conclusion and I know I was putting out somewhat of a ‘disconnected’ vibe.  I couldn’t help it, honestly.  We were saying our goodbyes at the door and there was this stagnant awkwardness in the air that I had never felt before.  Clearly, I didn’t want to see her again and I should have been honest about it.  We said our goodbyes and that was that.

Until…

The Date Aftermath

Photo: by SylviaJadePhotography via Flickr

A few minutes later my doorbell rang.  She must have forgotten something.  But she wasn’t in my house very long.  What could it have been?  I opened the door and she had this look on her face – like a jungle large cat eyeing its next meal.  The following conversation ensued…

Jess: “It seemed like such a shame to let my good panties go to waste.  Mind if I come back in?”

Me: “Ummm.  What?  Really?  Okay.”

I was dumbfounded.  Literally.  I stood there with a deer-in-the-headlights look on my face and I felt all the blood rush out of my head (and into my other). I didn’t turn her down but I should have.  Don’t judge too harshly; I’m not entirely convinced she wasn’t interested in a simple romp as well.  I did’t ask and she didn’t say. I knew I didn’t want a relationship with her, but she was literally at my door offering herself up to me.  Take note, ladies – if you offer sex to a man he’s not likely going to turn you down.  Men are weak.  I gave in.

Needless to say the experience was less than fulfilling and, given the opportunity I’d do things much differently if I had another go-round.  The sex was good but not fantastic.  I think to have really fantastic sex I need to have some sort of connection with the person I’m with.  You just can’t establish that sort of connection in three dates.  She left and we never really spoke again after that.  I did see her at the gym once quite a few months afterward.  We both saw each other and turned a Casper the Friendly Ghost white color.  Perhaps we’re both ashamed of what happened?  I felt awful and vowed I would never be in that situation again.  I’m happy to say that I’ve kept that promise to myself.

Lessons of the Day

There are two in this case…

1. Men will sleep with you even when they know they’re really not interested in anything else.
2. Patience is a virtue when dating.  Rushing into things (especially the ‘big’ steps) will almost always lead to failure.  Don’t rush yourself or others.  You can’t just hit a rewind button and go back once you take those steps.  You may be sabotaging a relationship that has real potential.

Part IV in the Dating Game series is a fun one, let me tell ya!  This is a story of a girl I met and went out on two dates with.  We hit it off great – we had good chemistry, great conversation and we were attracted to each other (presumably).  Then something happened after the second date…

“Bi the Way” – You’re Not Gay Enough For Me

Fear Factor: 6
What-the-hell-just-happened? Factor: 6
Good Riddance Factor: 4
Crazy Factor: 9

The Date Setup

It was February in Florida.  The weather was perfect outside and my life was just humming along.  I was eye ball deep in my dating experiences at this point.  I had a profile on Match.com, Plentyoffish.com and OkCupid.com.  I was averaging one or two dates a week and it was wearing on me.  Then I met ‘Brittney’.  Brittney actually found me on Plentyoffish.com.  I hadn’t really had the best experience up until this point on PoF.  The site seemed rather clunky, not very aesthetically pleasing and the people…oh, the people.  They were a whole other breed, let me tell ya.

I was checking my Email on PoF one afternoon and saw that I had an Email from Brittney.  I had seen her profile on the site before but didn’t send her an Email.  I wasn’t sure why – on the surface she had a lot of what I was looking for in a woman.  She was a single mom, good job, divorced a few years and her profile was pretty humorous.  Humor went a long way in my book.  She was cute, too.  Cute never hurts.  We chatted back and forth for a few days and decided to meet up.

The Date Plan

After a few days of the customary chit-chat, small talk and feeling each other out we agreed to make a plan for a first date.  We both preferred something informal and low-key so we went with a quick meet and greet at Starbucks.  Any girl that likes coffee gets bonus points in my book.  We met for coffee one weekday after work.  We sat and talked for at least two hours about anything and everything.  The conversation flowed, it was natural and it felt good for a change.  We had a great time, especially for a first date and said we’d definitely have to do a ‘real’ date next time.  Next time…what an unusual concept for me.

Valentine’s Day was fast approaching and I was so glad when Brittney initiated a conversation about the dreaded holiday.  We had only gone out on one date but even for a fledgling ‘relationship’ like ours, VD can make or break the whole thing.  Brittney was very cool about it and said that she didn’t expect a thing for VD.  In fact, she was busy VD because she had her kids with her that night so having a date night was going to have to wait anyway.  We made plans for the day after Valentine’s Day to have dinner at a Carrabba’s that was convenient to both of us so that we could meet after work.

Date number 2 went famously just as I had expected.  To random passers by we looked like a couple that had been dating for a while.  We ordered and shared our meals with each other even ‘feeding’ each other a bite.  We shared a bottle of wine, which likely fueled the conversation and chemistry that I was seeing to some extent.  The night went great and I fully expected a third date.

And that’s when she had a change of heart…

The Date Aftermath

After the second date we continued to talk almost daily.  The conversations started to take a turn for the weird two days or so after the second date.  I couldn’t quite put my finger on what it was but she was distancing herself from me.  I felt a Fade coming on.  I had seen it before.  Something ‘comes up’ and one person has a change of heart and decides it’s time to end the relationship by disappearing.  I didn’t freak out.  I didn’t really even care at this point.  I had gone through these motions so many times nothing surprised me at this point.  That’s when Brittney informed me of her recent revelation.  I remember it well.

Brit: “So, I’ve been thinking a lot lately.”

Me: “Oh yeah?  About what?”

Brit: “Well, to be honest, about my ex.”

Me: “Your ex?  Ok.  I thought you were divorced for a few years?”

Brit: “Yeah, we have been but I think we’re going to give it another try. It was nice meeting you, though!”

Me: “Haha yeah ok, good luck.”

Jealousy by cambiodefractal via Flickr

I admit I was a little miffed but I wasn’t surprised.  Typical dating game BS.  I wasn’t upset because nothing surprised me at this point.  That is, until I logged back on to PoF a few days later and noticed that Brittney’s profile was still up but had been…umm…updated.  She updated her profile to make it known that she was a freaky girl and that any man she dated would have to be freaky too.  How freaky?  She required that they be bi-sexual.  Now, I’ve been ‘dumped’ my fair share of times but I can’t say that I’ve ever been ditched in lieu of a dude that likes to hump other dudes.  Good for her for figuring that out and realizing that a bi-sexual man is something that is a requirement for her.  I find her requirement to be a bit unusual but to each their own.  I’m sure there is a specialty site out there to cater to her unique tastes.   But why give me the bit about going back to the ex?  Clearly that wasn’t the case.  She also can’t possibly be embarrassed because she put it on PoF for all the world to see.  Was she trying to save my ego by telling me it was the ex and not that I don’t like to do it with other guys while she watches?  The world may never know (but I’d sure like your thoughts!).

Lessons of the Day

1. Each person has a unique set of needs that only they can define.  If someone says you’re not the one for them, it’s normally not up for debate.  Take your lumps and move on.
2. There really is such a thing as a girl that likes to watch two guys go at it.  I thought the same-sex thing was fairly unique to men as a fantasy of girl on girl action.  Who knew?
3. I can be flexible in dating to an extent but I have my limits.  I will not take it from behind from another guy to appease a woman.