Preparing for the Worst

Thursday, December 31, 2009
I know it should read “Hoping for the Best”, and I am doing that as well, but mostly what I do in what I consider the worst time ever for dating, the first few weeks, is try to prep myself for what inevitably will be a loss of interest in my new potential beau (or his loss of interest in me).

I am certainly giving my new crush the benefit of the doubt, but I’m starting to get a little bit worried that I gave him too much credit off the bat. Usually I don’t believe anything a guy tells me, which I get a lot of flack for, but when you don’t know anything about someone why would you take what they say at face value?

Last week he professed to be direct and interested in me as girlfriend material. If I am to believe him this week then he is sick and very sleepy but very much missing me and wanting to see me. I present the following evidence that something other than that may be happening.

Exhibit A:
He cancelled on our Monday night date only a few hours before the actual game (and only at my prompting) so I wasn’t able to find a replacement for what is a decently expensive seat. He did call on Monday AM to say he was heading to the doctor, and he was very concerned I would bring another date when he said he wasn’t going to make it, but so far he hasn’t even asked me how the game went.

Exhibit B:
He texted me about getting together later this week. When I asked him what he had in mind he suggested we be naked. He added “lol” and when I told him that might certainly be part of the date but wouldn’t be the only thing we planned for he was in agreement. So I asked him again, what did he have in mind? He sent back something that made no sense along with “c p”, which I decoded via the internet later to mean “sleepy”. I called him later that night, but haven’t heard back yet so there are no plans on the table.

Exhibit C:
His voicemail doesn’t have his name on it. I know that maybe there are lots of people who do that, but to me it seems sort of shady and is therefore on the exhibit list.

I meet a lot of guys who talk a good game, who tell me I’m a great catch and how interested they are in me and that they’re not into one-night stands, blah, blah, blah. And then those guys ask me to get naked.

I’m not against being naked, that’s for sure, but there are two categories of men I get involved with and I’m really not able to think longer term with those whose eyes are on the naked prize.

To quote Janice from an old episode of Friends, “So like which of these two guys do you want to be?” As soon as he calls me back we’ll find out.

I Did Not See This Coming

Tuesday, December 29, 2009
Late Sunday night I received a phone call from a number I didn’t recognize that I let go to voice mail. Monday morning I noticed a text message from that same number. It read: Hi I know you don’t know me please call me it’s about a guy you dated that I have been with for the last 2 years. Thank you.

I waited till I got into the office to return the call and after a caveat statement saying this was the weirdest conversation I’d probably ever have I was asked if I had dated a man named Surf Dude.

Uh, hold the phone, please. Surf Dude?! The man who can’t even return a phone call? The man who had sent me hundreds of text messages during football season trying to get me to appear at his place? The man who just offered to cook me dinner and wanted to spend a romantic evening with me? The man I had just decided to give the boot to? Again?!

Over the next twenty minutes or so I was deluged with information, all of which I find fascinating and almost unbelievable. I couldn’t wrap my head around it, except to think that I had (a) never met the real Surf Dude and (b) had hit the blogging motherload.

First and foremost, I was the 5th of out 7 girls to return calls to the gal we’ll call Girlfriend #1. I didn’t think Surf Dude possessed the necessary fortitude it would take to carry on any deception, let alone several, but boy was I mistaken.

Girlfriend #1 seems to be a “real” girlfriend, who knows his family and has spent holidays there and has been dating him (with a few breaks) for the past two years. She happened upon his old phone, and due to clear shadiness on his part decided to investigate.

Based on her conversations, there are like 3 "girlfriends", and I have known him for just over two years, so I’m smack in the middle of the overlap period. He is actively talking to all of us, on and off. Some of the gems about the multiple relationships include:
  • A 19-year old girlfriend (he's 32 or so)
  • A woman who is apparently heartbroken that he's dating a whole harem
  • A women who has lent him a few thousand dollars (yet to be repaid)
  • A women who is “hooked up” with our city and Surf Dude has reaped the benefits of free everything, from hotel rooms to the basketball tickets he was supposed to score for he and I this upcoming weekend!
  • A whole host of naughty photos sent to Surf Dude’s phone
  • Multiple reports of issues in the bedroom (I can't report on that, btw)
Oh and also he’s apparently broke, perhaps due to his potential gambling and drinking problems.

Fortunately, I’m only on the periphery of the deception. After all, we’ve only gone on a handful of dates spread out over a lot of time and I picked up on his flakiness right away. I've never bought him anything more expensive than a beer. Appears I got off easy (well, that or these women REALLY need dating advice).

Girlfriend #1 was gathering information with which to hurl at Surf Dude when she picked him up from the airport Monday. What I wouldn’t give to be a fly on that wall! To the end, I’ve already sent the friendly text to see if I can be a “friend” to him… and I'm passing along my blog to her.

The Week in Review | 12.21 - 12.27

Sunday, December 27, 2009
Twice in a row I have a weekly update!

Abandon the Ship!
Even though I was thinking about coaching Surf Dude on good dating practices, I have decided instead to completely throw in the towel. Last week I invited him to join some friends and I at a basketball game (my alumni playing in Chicago) and he was all over it, especially because they were playing one of his favorite NCAA teams. Tickets were sold out, and he said he might have a line on free tickets. He said he needed a day and I haven’t heard from him for the past four. Including no holiday message. The game is next weekend, so we have to get moving. And we will, but he’s no longer on the guest list. Enough is enough.

My New Catch
One of the things my new love interest had in his Match profile was that he’s looking for someone adventurous, spontaneous. And it just so happens he’s a Vikings fan and I have tickets to their game against the Bears tomorrow. So on Christmas Eve, the day after our date, I called him up and invited him to the game (which then required me to bump the individual I had invited before). He said he was in (because I’d be there) but would need to go find some outdoor gear. Look at me! I’m being impulsive! It’s cold here in the Chi… I foresee snuggling in my future…

Merry Christmas to Me!

Saturday, December 26, 2009
Even though I’ve spent the better part of this year making sport of the dating deficiencies in the men I seem to attract I clearly ended up on the “Nice” list. I received an early, awesome Christmas present on Wednesday in the form of my latest first date.

We met on in short order. Wink (his), email (mine followed by his), phone call (mine), date suggestion (his). We met for drinks (his suggestion) at a bar where we could catch the basketball game (my contribution). Simply put we hit it off.

I won’t bore you with the adorableness of a great first date (except to say there was hand holding while walking the streets of the city while it snowed) but I will say this. When you meet someone you have chemistry with, you know right away. I think I had forgotten what that feels like - it’s exciting and nerve-wracking and full of promise. Lesson #1: No one should waste their time trying to manufacture chemistry. Just keep looking till you find it.

The other thing about this one is I think I’ve met someone who will actually be a good personality match for me. For awhile now I've been thinking (read: know) I should date someone who’s more type A than I, someone who says what he thinks and goes after what he wants. This guy is super direct, focused, and kind of intense (in a way that makes him even hotter than he already is).

I will have to seriously step up to the plate to date this man. You see, even though I am perfectly capable of stating my mind in my non-dating life, I get all insecure like in my dating life. I think I seek out relationships with guys who won’t expect me to talk about feelings and such, who aren’t capable of being that strong guy presence. Those relationships don’t work, because I'm holding back, waiting for them to drive things forward and they never will.

That will not be the case with this man, and he deserves someone who is available and honest about what they're feeling. Lesson #2: Put yourself out there. When you do meet someone you click with, don't hold back (especially if it challenges some of your dating insecurities).

So I’m excited, a little nervous, and hopeful. More to come on this one, say early next week after our already scheduled Monday night (football) date?

Dating Imitates Work

Wednesday, December 23, 2009
Surf Dude is a project. He’s a project in that I don’t think he knows what he should be doing to push our relationship forward and most of what he does do seems way too advanced for where we actually are.

I say all the time that I don‘t want a dating project, which is ironic since what I do for a living centers around project based work. I work with companies that interact with mine, walking them through a process to get them ready for new or changed aspects of the data that goes back and forth between us. I lay out a time line, the different steps of our testing, applicable dependencies and such. I provide status as to their progress, whether they’re on track to complete by the deadline or whether they’re falling behind. I get a great deal of satisfaction when I am able to bring a business partner up to par and successfully sign-off on their readiness.

Why wouldn’t I want to use some of those skills in my dating relationships? Presumably someone who’s still single (but would prefer not to be) hasn’t gotten it right yet and may need some coaching to sustain a successful, longer term relationship. I get assistance from my friends, why couldn’t I be more vocal with guys I’m involved with to try and coach them?

I’m not going to make a project plan, of course, not going to identify dating milestones and tell him that his status is Yellow bordering on Red. I can let him know what I’m looking for, specifically, in terms of moving our relationship forward though. And I can see whether he is interested and/or able to do that. If not, I can walk away from it knowing I really gave it a decent shot.

Surf Dude may be like that super difficult client I had at the beginning of this past year. They were weeks and weeks behind schedule and yet I was able to whip them into shape and launch them on their desired go-live. It wasn't always easy, but with the right amount of pressure and assistance they were soon on their way.

Maybe Surf Dude just needs a map to my heart. Fortunately for him I'm excellent at graphical representations of projects, too.

The Week in Review: 12.14 - 12.20

Sunday, December 20, 2009
This likely won’t be a regular weekly posting, because (sadly) not all weeks deserve a recap, but this week I have a few things going so here we go.

Two Ships that Text in the Night
Surf Dude and I continue to experience seeming insurmountable scheduling difficulties. After weeks of useless texting he proposed an actual date, but I ended up needing to work right through the dinner he was going to make. Rescheduling during the week is tricky (he normally works till 10/10:30p which is when I’m usually getting ready for bed) and then Thursday he left for California, where he will be for the entire time that I’m off work. He literally comes back the day I go back to work, which means he’ll be right on time to say “no” to getting together on New Years Eve.

No Nibbles
After an initially decent level of interest on the last few weeks have produced no new interest in my online profile. I’ve got 2 ½ months more to make something of it, though, since the subscription auto-renewed instead of canceling when my friend thought it would. The up side is that her credit card was charged since I’m borrowing her original subscription.

A New Fishing Hole
Last night I went to a party thrown by the sister of the roommate of my friend’s boyfriend. I knew only my friend and was hoping to make some new acquaintances. Unfortunately most of the folks there were already in couples, and instead of trying to identify and meet the few single guys I instead made a new girlfriend. The night wasn’t a total loss, besides being able to share a cab she’s new to the Chi and has serious potential to step into the currently vacant role of “single gal pal”.

Oh and of course my friend told her boyfriend he needs to find me a guy. It can’t hurt, clearly I need all the help I can get.

"Top Matches"

Friday, December 18, 2009
I get this daily email from with “top matches selected just for me”. Somehow I don’t think there’s too much going into the pulling of these so-called matches. Snapshots of the profiles include the photo, and the following info.

(1) Age / Location. Age, at least, does not appear to line up to my specified range, which I would think is one of the easiest things to match on. Unfortunately there are a zillion people from Chicago on Match, so that's hardly narrowing it down for me.

(2) % Match. So far I haven’t gotten higher than 86% on the email, a B+ if you're grading on the curve.

(3) Height (in Inches and Centimeters). Sometimes it also adds “Slender” after the height. I think the male appropriate term is actually “Slight”, but the odd thing is that’s the only physical attribute that appears on the email, not “average” or “stocky” or whatever the others are. I don’t like slender so maybe they’re warning me?

(4) Age Range of Women He Seeks. I like how some guys have round numbers, like 25-35 and others are really specific, like 23-31. There are the typical huge age ranges, like 24-42 (for a 35-year old), and then the exclusively younger range, like 24-31 for a 33-year old. Of course all men go WAY younger than their own age.

(5) Previous Relationship Status. The most frequent answer is “He has been in committed relationships but was never married”.

I don’t know how I answered this question on my profile, but if I was being honest I should have been looking for the “I haven’t been in a stable, committed relationship in years, but I regularly get over attached to men I’m not in committed relationships with and now feel I’m ready for said stable, committed relationships” option. Doesn’t this option just mean “Never married”? No one will admit to never being committed so this hardly seems like an accurate assessment of anything.

(6) Faith. This is a pretty basic stat, but how could I be an 86% match with someone who is Jewish when I explicitly excluded it from the list of religions I would match up with? I’m pretty open on most comparables but I’m fundamentally not Jewish and won't be a match for anyone identifying himself as such.

(7) Kid Status. “Someday, He will want children”. I love this one, I think because of the way it’s annotated. It seems wistful.

Focusing on the details of the presentation instead of the content is obviously not the purpose of these emails, but since at this point I’m mostly letting men come to me it hardly seems necessary to do anything but critique them. The emails, that is, not the men. I’ll be saving that for when they send me an email, obviously.

Wonders Never Cease

Monday, December 14, 2009
I have a confession, dear readers. I have not stopped texting Surf Dude despite haven officially given him the blog-boot about a month ago (see Wipeout: Surf Dude). Perhaps most disturbing, I have managed to rack up around $40 of additional cell phone charges this past month due exclusively to texting him. Clearly I have a problem.

Sometimes he starts it, sometimes I do, and we often talk about meeting up (usually one of us is tipsy during this exchange) and then we never do. Last night, though, the craziest thing happened. I invited him to come over to watch Elf, one of my most favorite holiday films. He wanted me to go over to his place. We went around a few times about each other's places via text and then HE CALLED ME AND ASKED ME OUT.

That isn’t even the craziest part. Listen to the date he proposed:
  • First, he picks me up and brings me to his place, where he cooks me dinner
  • Second, we go to his basketball game (he’s very serious about not missing it) and presumably I cheer
  • Third, we head back to his place for a movie, which we fall asleep watching
  • And finally, I stay over and the next morning HE DRIVES ME TO WORK
Woah, I say, that’s a pretty big plan. After I make him repeat it I realize that he wants me to get ready for work at his house and go straight to the office. Surf Dude and I never got anywhere near the stage where I would get ready for work at his house, I've actually never even been AT his house.

After months of not being able to ask me out at all he practically invites me to move in with him. Am I the only one who thinks there’s a progression from strangers to casual dating to serious dating? (the answer to that, by the way, is clearly yes). But I’ve got to give it to him for trying to suggest a normal date and saying Yes doesn't really hurt any.

We settle on the dinner part for sure, with me driving myself so that I can leave (I was given the options of him picking me up directly from work or at my house) anytime during his 12-hour plan that I deem appropriate.

Surf Dude has a terrible record for follow through, so I’ll let you know whether he even remembers to send me his address.

The One That Got Away (part 2 of 2)

Saturday, December 12, 2009
He called the same day he got my number. The first few calls were awkward. We played the name game with old work pals and talked about where we were in our lives (me: content and happy although still unlucky in love, he: going through a lot of changes, most positive, but still very bitter about his divorce). We talked a lot about our past relationship with each other.

We had completely different perceptions about the relationship. He thought I had all these negative conceptions of him when I felt like I knew him better than he knew himself back then (and liked him anyway). I had never told him how miserable I was when we had been together because of work and other relationships; he had thought I was happy. We had both fallen for each other, but neither of us had been honest about their feelings. And now? He felt really guilty, I had no regrets.

The talking got easier, some of the banter came back, and we sort of established a new friendship. But all along there was this undercurrent of a potential romantic reconnection.

We didn’t talk about a new romance, of course, but I at least wondered about one. I wanted to see him, in person, just to see how I felt standing in front of him. I thought I would know right away.

There was a missed opportunity when I was in a nearby city visiting friends. We didn’t talk for awhile after that. And then a second opportunity came up, when I was again going to be in that nearby city. I waited to hear back from him, and when I didn’t I realized I needed to put it all on the line, again.

We had been talking for about six months and I knew how I felt. It was the same as before - I thought we could work. I know we might not, too, we had a lot of the same obstacles. I am a very different person than I was back then, more mature and less afraid to talk about my feelings and needs. There was still something between us, though, and I needed to know whether we were headed that direction or not.

He said not… because of the distance, because of the time a relationship takes, because of what he wants to do with his career right now. I told him he was making a mistake, again, and then I deleted his phone number.

If there’s a moral to this story it’s that you have to put yourself out there or else you‘ll never know. I did that, I did it back then and I did it in October. And he never will. Not back then. Not even now.

Exactly 32 hours and 2 dirty martinis after that call any trace of sadness at love lost was gone. I surprised even myself, I’m normally really sentimental and romantic when it comes to potential loves, but like I said, I’m a different girl. I’m the kind of girl who jumps in with both feet and I won’t be happy with anyone who won’t hold my hand and jump with me.

Back then I thought he was the one I let get away. And now I know I was wrong. In this relationship, I was the fish.

The One That Got Away (part 1 of 2)

Tuesday, December 8, 2009
Let me tell you a story. It’s a story about a girl who fell head over heels for a guy. And he fell for her, too, only there were a few complications. They worked together and both traveled, neither was from the same state, so it didn't seem like a relationship would work outside their current situation. The girl wasn’t really in the right place to have a serious relationship and the guy had just gotten out of one. It was difficult, sometimes, but they had an undeniable connection with each other. Then they got hit by a seemingly impossible hurdle - midway through their courtship the guy got back together with his ex-girlfriend, something about the "sure thing" that she was and the riskier option that the girl was. And then the girl changed jobs and they were both working and living in separate states.

The girl thought that would be that, but once she left they still talked all the time. She realized that she really, really cared about him. So she put it all on the line, and told him that she wanted to give a real relationship a try. Two weeks later he proposed to his girlfriend.

The girl was pretty devastated. She felt like she and this guy really had something - because, dear reader, they really did - and that she had ruined it by not addressing her feelings earlier. She felt like he was The One That Got Away.

She also felt the guy was making a terrible mistake. But he got married, and she got over it. She had really, truly moved on, until almost five years later when he ran into an old co-worker of theirs who still had her email and gave it to him.

At first she didn’t want to talk to him at all. She assumed he was only writing because he’d gotten divorced (which he had) and possibly that he wanted to get back together (which he had crazy romantic ideas about). She was worried there would be this flood of sad emotions about what could have been if she opened that door.

Instead she had the same crazy romantic thoughts. Not without a good dose of caution, she was very aware that a lot of time had passed, and that the girl that fell in love with that boy was a great many years wiser and significantly more assertive. Who knew how different the guy might be, plus he was still hurting from his divorce. There was a lot of history, but she couldn’t deny her heart.

And so I gave him my phone number and waited for him to call.