Chicago Boy – Not sure what happened here, but sorry things didn’t work out!  It happens, no big deal.  Just wanted to say thanks again for the sushi, drinks, etc., and it was nice to have met you.  Best of luck.  : )

Take care,
~DD

This email accomplishes the following:

1. I accept a little vulnerability, but get a little closure
2. I end on a high note – courteous, friendly, respectful, mature
3. I feel a little better about the situation

Worth the 5 minutes it took me to write and send it.

I was having such a nice, peaceful night last night when Chicago Boy bursts out of nowhere and sends me the most retarted text ever, leaving me with a pit in my stomach that almost kept me up half the night.  What the fuck, loser???  What do you want from me???  Why must you torture me like this?  The funniest part of it was, just like so many other men I’ve come across, this guy REFUSES TO CALL ME like a normal human being.  Here’s the txt conversation:

Him: How was ur weekend?

Me: ?? you never returned my text from lask wk.. call me if u want to talk

Him: Im sorry… Which text?

Me: call me if you want to talk

Silence.  OF COURSE he didn’t call me.  I don’t care if my “call me” texts came off harsh.  His ignoring me and dropping off the face of the earth was just SLIGHTLY harsher, in my opinion.  Give me a fucking break, I mean really.  I just cannot figure out what his purpose in contacting me was.  Does he just want to get laid?  Does he think I don’t care that he was ignoring me?  Are his other chicks busy and he’s bored and looking for entertainment?  Is he really just THAT clueless and doesn’t realize that disappearing off the face of the earth for almost a week was going to send me the message that he’s not interested???  Is it even POSSIBLE that he was too dense to realize that???

WhatEVER!!! This dude is driving me fucking crazy, and I can’t take this shit.  Fuck off, loser. 

Alternatively, you have the option of picking up the phone and talking to me in a civilized manner like a normal human being.  Anyone care to place a bet on the chances of THAT happening?  Riiiiiiiight.

I talked to the new male prospect about this guy the other night, and he gave me the official guy-friend opinion.  In fact, he totally laid the smackdown.  He was like, “DD, I’ve gotta be honest, sometimes when I’m dating a girl and I’m not totally crazy about her, I just keep seeing her so I can get laid and have someone to hang out with.”  Hey, I can understand that.  I’ve done that myself.  No big deal.  BUT, I still insist that the whole disappearing/reappearing magic act is rude and immature, and if you just want to hang out and fuck, you could at least acknowledge it and act like a mature adult.  Last time I checked, we were adults.  Whatever… I’ve already wasted more time on this guy than he deserves simply by writing this whiny post about him. 

But let the record show that, for a while, Chicago Boy was actually a total cutie pie, and I did have a great time with him, especially on that awesome first date.  Plus, when I spent the night at his place, he was amazingly cuddly and affectionate and I could have just eaten him up with a spoon.  Aww, how sappy.  If nothing else, he entertained me for a few weeks and brought out the schmoopiness gene which had been dormant for a while.

Then again… the fact that he REFUSES TO CALL ME just burns my sweet little ass to no end.  It’s all very reminiscent of Hot Marine, and we all know how THAT worked out.

Next!!!

Holly Hoffman wrote a great post a few months ago entitled “News Flash: Sex is a Distraction.”  Go check it out if you haven’t already.  She makes a lot of great points, the biggest of which (in my opinion) is that dating and the pursuit of sex can engulf your entire life, leaving the other components of your life to wither away out of neglect.  To add to that, I think dating/sex has not only left my interests and career on the back burner, but it has been killing my brain cells, one by one, one bad date and one missed phone call at a time.  I’m turning into a useless shell of a person, and I can’t fucking stand it anymore!

First of all, I want to get one thing out of the way: I need to trust my gut feelings, no matter what.  I’m getting better at it, but there is still that idiotic teenage-girl part of me that wants to hold on, make excuses, put on the blinders, and ignore all the neon signs flashing right in front of my eyes.  As I’ve mentioned in previous posts, I’m a big fan of the book “He’s Just Not That Into You” by Greg Behrendt and Liz Tuccillo.  It’s hilarious and light-hearted, but more importantly, it slaps you in the face with common-sense relationship advice that you already know but have conveniently been ignoring.  Allow me to pull out a few quotes to remind myself of what an idiot I can be and how simple dating really is, when you get right down to it:

We like taking a break from our generally mundane day to talk to someone we like.  It makes us happy.  And we like to be happy.  Just like you.  If I were into you, you would be the bright spot in my horribly busy day.  Which would be a day that I would never be too busy to call you.

DUH.  Of course!  It’s so simple.  DD, are you listening?  This is important.  Another one:

When I was working with Greg on this book in New York, I noticed that Greg would often call his wife just to tell her that he couldn’t really talk to her right then, but he was thinking of her and would call later.  It didn’t look like the most difficult thing in the world, but it sure seemed nice.

Hello?  People who give a shit will find 2 minutes to call.  It doesn’t take a genius to figure this shit out.  And finally:

100% of men polled said they’ve never been too busy to call a woman they were really into.  As one fine man said, “A man has got to have his priorities.”

Enough said.  DD, if it takes a relationship book to put this stuff in black and white in order for you to figure this out, something has gone horribly wrong.  I’ve turned into an idiot!  Really, it’s unbelievable.  I did NOT spend all those years buried in a university library to fail so miserably at common sense.  I need to climb out of this hole and get back to my normal, productive life as a decent human being and industrious member of society. 

Case in point: Remember “the incident” from last fall?  Here are some numbers to put things into perspective: We “dated” for six weeks.  It took one day for the entire thing to explode in my face.  I spent FOUR MONTHS being completely depressed, holed up in my apartment, hating myself. 

Another one: Hot Marine and I went on five dates over the course of about three weeks.  He stopped returning my calls over a weekend (say three days at most).  I spent two months being horribly depressed, getting drunk alone in my apartment every night, and yes, hating myself.  I spent another few months crawling out of the hole and back to my normal life.  It was about a year and a half before I was finally “mostly” over it.

One more: Mr. Perfect and I went on probably 8-10 dates over the course of maybe about six weeks.  We lived about 15 minutes apart.  Despite numerous attempts on my part, I didn’t see him for two whole weeks.  Over the course of those two weeks, I made up every excuse I could think of and was STILL convinced that he liked me.  He stopped returning my calls over a weekend, and then I found out he had gotten back with his ex during the initial six weeks we had been seeing each other.

What the hell is wrong with me that I allow myself to be completely consumed by this bullshit?  I know I’m smarter than this.  I know my brain cells were functional at one point in my life, and I don’t know how I got myself into this situation.  Today I spent the entire day staring at my cell phone, waiting for Chicago Boy to return my text from last night.  I had my phone right next to my keyboard on my desk ALL DAY.  I slept with my phone on my nightstand last night.  I took the phone into the kitchen while making dinner, and yes, even into the bathroom.  ONLY CRAZY PEOPLE DO THIS.  There is seriously something wrong with me.

The saddest part about all this is that the rest of my life is withering away.  My hobbies and interests have atrophied.  My career is coasting along.  I haven’t been returning phone calls from “successful” (read: married) friends because I can’t bear to hear how happy they are.  This is NOT RIGHT.  This is NOT ME.  I hate it!  I really need to stop all this bullshit and get back to my normal self, my productive, happy, interesting self.  Also, I need to start thinking like a 29-year-old woman, not a 15-year-old girl.  If my gut is telling me that it’s over, chances are, IT’S OVER.  No more making excuses, no more holding on, no more putting on the blinders and shutting out reality.  I’m better than this, and it’s about time I sacked up and started acting like an adult.

This is a public confession.  Feel free to hold me to it.

**********

Because I am a total dork, I whipped up the following relationship timeline:

And here’s the  narration: regular letters (A) are me, prime letters (A’) are every random guy I meet:

A: Oooooh, I seem to have met a nice guy.  Awesome!
A’: Hmm, I met a cute chick who might actually sleep with me.

B: I went on a few dates with this guy and have deemed him quality husband material.  Yay!
B’: Yeah, I really think this chick might sleep with me!  Awesome!

C: What a great guy – he cuddles with me after sex.  Still husband material.
C’: BOOBIES!!!!!!!!!!!!!

D: This sex glow is so great.  I heart dating.  I heart relationships.  I wonder if my parents will like him…
D’: Look, this other chick has even BIGGER boobies than DD… hey baby, how you doin’?

E: Maybe he’s really busy with work.  Maybe he lost his cell phone.  Maybe his phone ate my messages.  Maybe he’s in the hospital.  What did I say?  What did I do?  Why isn’t he calling me???????

F: Reality hits.  I have been ditched, again.

G: What a jerk.  But he was so cute and so nice and so cuddly….

H: My affection slowly dies a slow and painful death as I drink my way into a coma.

I: I finally get over it, many, MANY months later.

**********

I think I hit point F tonight, and I think Chicago Boy hit point D’ Saturday afternoon after our little sleepover.

WHATEVER!  I’m done with this bullshit.  I’m a smart woman who knows better than to fall into this same stupid cycle every single time.  Right?  RIGHT???  I really need to remember that.

Here’s how it went down:

I wanted to get together with this guy that I’ve been seeing – who shall henceforth be known as Chicago Boy – at some point during the weekend, but turns out that the only time we were both going to be in town was Friday night (last night).  He was free, but I already had plans to do dinner/dancing for a friend’s birthday that night.  We went back and forth trying to find an alternate time to meet up, but it just wasn’t working out.  Sooooo, I decided to invite him along for the after-dinner birthday festivities with a handful of my friends.  Good idea?  Bad idea?  It was too late to really think about it because by the time it hit me that our third date was going to be with a bunch of my friends, I had already invited him along and it was too late to back out.  So, I went with it. 

After dinner, my friends and I met up with Chicago Boy at a bar, and we all hung out for a few hours drinking beers, chatting, etc.  To my surprise (and relief), my friends seemed to approve, and he really held his own during the conversation.  Thank god!  I was bracing myself for disaster, but this part of the night actually worked out really well.  I even felt comfortable enough to run to the bathroom at the bar, leaving Chicago Boy to fend for himself with my friends for a few minutes.  He even bought us all a round of drinks.  Excellent!

The bar scene was kind of dead last night (at least at the few bars that we went to), perhaps because last weekend was St. Patrick’s Day, and maybe this weekend everyone was just taking a break or something.  Whatever.  It was kind of a bust in the dancing department, so we all decided to part ways for the night and head home.  I said goodnight to my friends, which left me and Chicago Boy to our own devices.  We decided to head elsewhere for one more beer, and we wound up in a very cute little bar that I don’t go to often enough.  Must add this to my list of regular hangouts.  We chatted there until about 1:30 or so, and the conversation and flirting and all that good stuff was going pretty well.  Again, thank god this part of the night was going well because little did I know what I was in for later on…

After we leave the bar, he invites me back to his place, and of course I am more than happy to oblige.  I say something like, “Ooooh, I get to see the bachelor pad!” through my drunken haze.  Real classy, DD.  Nice one.  At this point it was 100% obvious to the both of us that we were headed upstairs to hook up, and once we got into his apartment, we just headed straight for the bed and got going.  I walk into his bedroom and am surprised to see what I think is the biggest bed I have ever seen in my life.  Dudes, this thing was GIGANTIC.  He said it’s 8 inches wider than a king-size bed, and seriously, I believe it.  You could probably fit five or six people comfortably in this thing.  Killer.  And what a nice playground for me and Chicago Boy to play in! 

We start making out and almost instantly his hands are in my pants and I am playing with the cock.  Clothes are flung in all directions, and before I know it we’re rolling around naked in his huge bed.  Now, my dears, here’s where the disaster begins.  First of all, although I think Chicago Boy is totally adorable and we’ve been getting along pretty well, the first time in bed with someone can be a little awkward, and this was the poster child of awkwardness.  What the fuck, right?  Wasn’t expecting that.  But here’s the real problem: remember how I had some gynecological-related drama a few months back and haven’t had sex since?  Ummm, yeah.  I was surprised and extremely embarrassed to learn that one cannot just go having sex full force after something like this, and, well, it just didn’t work.  Also: ouch.  This only added to the awkwardness.  So we didn’t have sex, but instead just fooled around for a while until we both kind of just crapped out from being tried, being drunk, and getting a little frustrated with the total awkwardness.  Ugh. 

As we’re basically collapsed/cuddled up and drifting off to sleep, I notice two things: (a) his bed is seriously the most comfortable bed I’ve ever had the pleasure of sleeping on in my entire life – it was unbelievable how amazingly comfy this thing was; and (b) that “ouch” I felt earlier was something that definitely needed to be investigated in the bathroom.  So I get up to run to the bathroom (also to get some mouthwash – I hate going to bed without brushing my teeth – eww!), and I realize that some damage has been done in some extremely hard to reach places.  Shit shit shit.  There wasn’t much I could do about it in the middle of the night, so I resign myself to just get some sleep and see a doctor first thing in the morning. 

And here’s where the disaster continues: I walk out of the bathroom into a dark hallway of an apartment that I’ve never been in before.  I am tired and still kind of tipsy and worried about whatever I had just done to myself in my lame attempt to have sex.  I guess I wasn’t really paying attention to where I was going because suddenly I walk right into this HUGE metal/slate hallway table and manage to create a massive gash on my thigh.  By this point I am cursing and screaming and really not doing well at all.  I make my way over to the bed and Chicago Boy is trying to decide if he should be worrying about me or laughing hysterically.  I think he was doing both.  I was so delusional and in so much pain that at one point I uttered the phrase, “I want my mommy.”  Again, nice one, DD!  Way to attract a man.  We proceed to laugh and laugh as I am doubled over in pain and trying to predict just how big of a bruise I’ll have in the morning.  He said he could already see it forming on my thigh, not 5 minutes after I crashed into the table.  Oh god, I am SUCH a dork, I swear.

So after all that drama, we finally stop laughing and fall asleep in the super-king-size, super-comfortable bachelor pad playground of a bed.  It was cute that we actually cuddled up all night, and it was nice to have that kind of close contact with another human being.  I had missed it, to be perfectly honest.  I fell asleep entangled in his arms and legs.  Aww. 

We woke up this morning in a fairly good mood, considering that I had basically maimed myself and we didn’t really get all that much sleep.  He had to be out of the apartment early, so I got dressed while he showered, I kissed him goodbye, and we both headed out.  And that was that.  Immediately after I got home, I hopped in the shower, surveyed the damage to both the girly bits and my poor thigh, and made my way over to the closest urgent care center I could find.  A few hours and several embarrassing conversations later, I was armed with antibiotics and instructions to make an appointment with my regular doctor when the office opens on Monday.  And the bruise on my thigh is getting bigger and uglier by the minute.  Sigh.

So that was that, my dears.  Am I a walking dating disaster or what???  I seriously don’t know whether to write off last night as somewhat of a success (Chicago Boy and I continued to get along well, and hanging out with my friends went well, and he seemed to stick by me even after the sexual fiasco) or a total disaster (I completely embarrassed myself in more ways than one and am probably out of commission for any further sexual activity for several weeks; I’m sure that will go over REALLY well).  Ahhhhhh.  I’ll tell ya, if this guy ever calls me again after what happened last night, he will win major brownie points for embracing an injured and completely uncoordinated mess.  If he doesn’t, well, I’m sure I’ll have the opportunity to embarrass myself in front of another eligible bachelor soon enough.

I swear, dating will surely be the end of me.

P.S. – Ouch ouch ouch.

Dudes, Friday night was so cute.  He picked me up in his convertible (!) and we headed over to one of my favorite local sushi places.  We got lucky and were seated in the back corner, a few tables away from the sushi bar – a good, relatively quiet, out of the way spot to sit and talk for a while.  We ordered a glass of wine and chatted until the food came.  He voluntarily offered the story of his divorce.  I would never have asked, but he just came out with it.  It actually wasn’t as bad as I thought it might be, and, to be brutally honest, I think it’s totally hot.  I mean, you know how guys are always more attractive when you know another woman wants them?  I found it totally hot that he’s been married and divorced, and especially because he seemed to be so upfront about the whole thing with me.  He handled the conversation pretty well, and I was just eating it up with a spoon.  Putty, my dears.  I was putty in his chopstick-wielding hands.

We finish dinner and head over to a semi-swanky bar down the street.  (Little did I know at the time, but a good friend of mine was actually hanging out at the same bar at the same time as us.  Too bad we didn’t see each other!  She totally could have checked him out for me.  You know, an objective opinion that wouldn’t have been clouded with the sappy date haze that I had been swimming in for the better part of last week.)  We sit at the bar, order drinks, and keep chatting for another hour or two.  At one point I went to the bathroom and was happy to find him still there when I got back.  Is it just me, or is this a mortal fear when out on a date?  Even when things seem to be going well (as they did on Friday night), a little part of me always wonders if he’ll split while I’m in the bathroom.  I’m paranoid, I know.  Hahaha.

When they started really pumping up the dance music and dimming the lights, we decided to ditch the bar because we couldn’t really hear what we were saying anymore, and I definitely wasn’t feeling the dance vibe at this place.  He held my hand and put his arm around my waist as we were walking back to the car (which he had been doing all night, by the way; how cute! A guy who actually holds my hand in public – shocking), and he drove me home in his hot little car. 

We arrive at back at my place and start making out in his car.  Yum yum.  Even though we had kissed goodnight earlier in the week, and had kissed hello at the beginning of the night, this was the first real kiss, know what I mean?  His lips were oh-so-delicious.  I ran my fingers through his hair.  My hands started roaming around as if they had a mind of their own.  I was somewhere around his chest/stomach when he put his hand on mine and slowly moved it down until it was firmly planted on his crotch.  Nice.  So I played around with the goods (through his jeans) as he let out a few “mmmms” as we were kissing.  By this point his hands were up my shirt, fondling the boobage, and at one point one of his hands made its way down the front of my jeans.  Delicious.  Of course, I was totally prepared with my oh-so-smooth skin and sexy underwear.  Yum yum yum.  I was really having a hard time resisting the urge to invite him upstairs, but I held my ground in an attempt not to ruin things by jumping in bed with this guy, which always seems to happen.  So I said goodnight, got out of the car, and that was that.

Then I proceeded to get upstairs and bang my head against the wall, totally regretting the fact that I let him drive away.  Ahhhhhh…

Anyway, it was a fun night.  The conversation at dinner and in the bar was cute and fun, there was a lot of hand/arm/leg touching throughout the night, and the high-school-esque making out in the car at the end of the night was hopefully a taste of things to come.  I’ve gotta be honest – I think this guy is adorable and a genuinely nice, normal guy.  Hopefully he feels the same about me.  We’ll see what happens from here.  : )

Friday night: The second date.  Verdict = : )

Saturday night:  First date with a different guy.  Verdict = Eh.

Well, was that the crappiest blog post ever, or what???  My fingers are absolutely dying to type up all the cute little details from Friday night, but I’m just so afraid of what happened last time, you know?  Maybe I’m just in a weird mood right now, but I just can’t do it.  Sorry, my dears.

Behold, my second date checklist:

• When: Friday night
• Plans: sushi for dinner, followed by something else TBD
• Eyebrows: plucked
• Almost entire body: shaved
• Outfit: still mulling it over…
• Hair: have penciled in a pre-date appointment with the curling iron
• Stomach: butterflies
• Head: in the clouds
• Heart: pounding
• Sexy underwear status: ON

BRING IT.  : )

The night was just really fun, plain and simple.  Everything went smoothly.  We got along really well.  It is almost surprising how seamlessly everything blended together.  I met him in front of the restaurant, and I liked him immediately.  He was cute and clean-cut and flashed me a big smile when we met.  Very nice.  We had a few beers and chatted for a few hours, telling random stories back and forth.  I leaned in, he leaned in, I “accidentally” brushed my knee up against his under the table.  He picked up the check less than 5 seconds after it hit the table without even breaking the conversation or letting me see the total or his credit card.  As I’ve mentioned before, this is the right way to pick up a check on a date.  Of course, I offered to split it (as I always do), but he wouldn’t have any of that.  He suggested that we check out a bar around the corner.  I took it as a good sign that he wanted to hang out for a bit more. 

Oh, and he wore the appropriate male date outfit: jeans and a dress shirt with a little gel in his hair.  Guys, I’m telling you, this is the standard date outfit that girls expect.  This guy was all over it.  Nice.

We head into the bar and find an old-timey bartender and a random old guy at the counter – and that’s it.  So much for the bar crowd on a Monday night!  We spend the next hour chatting with the bartender and the old guy (and another old guy that came in later), trading dirty jokes and – believe it or not – magic tricks.  It was hilarious.  We were cracking up the entire time – half laughing with them, half laughing at them.  About halfway through, we start holding hands under the counter – so cute – and later I planted my hand on his knee.  Later on, our legs were permanently brushed up against each other, and I started purposefully leaning in as I laughed at whatever the old-timey guys were saying.  He started leaning in as well, and it was so cool to see that he seemed to be into me just as much as I was into him.  Killer.

When we left, he gave me his arm and I took it, and we walked down the street a bit.  As we said goodnight, we leaned in simultaneously and kissed – just a short little kiss, but cute nonetheless.  Open mouth, no tongue.  Short and sweet.  He suggested hanging out again this weekend, and I agreed.  And that was that.

Such a fun night, right?  It was nice to actually feel a good connection with someone, and it was really nice to plant my lips on a cute male specimen again.  Looking forward to round 2.  : )

Edited to add: We have been texting back and forth tonight and just traded “: )”.   Oh, the cuteness!!!

I looked fabulous.

We busted each other’s chops back and forth all night.

Hand holding and knee touching under the table.

Kiss goodnight.

I still smell like his cologne.

: )