The Shy Guy: Two Years Later

So the Shy Guy, who has since earned the nickname WIMB (Work Instant Message Boy), and I played this instant message game for months before anything happened. I kid you not: awkward hellos at the coffee bar, random (though rare) flirtation at the gym, and of course - lots of random IMs.  I felt like, despite our minimal in-person interactions, we were getting to know each other pretty well.

I could not for my life figure him out though. Why wasn't he asking me out? Asking to hang? Maybe asking for my PHONE NUMBER? ANYTHING?

We exchanged numbers one Thursday night last Spring (2011) when a bunch of work people were at a local bar. He was pretty drunk, and I got some jibberish late night texts.  Asking me to come over or something I imagine. I was distracted by a car full of friends forcing me to go through the McDonald's drive-thru.

A month or so passed, and we started playing extremely competitive games of Words with Friends. I backed off on the IMing, but WIMB would essentially narrate every game and comment on every other word I played.  One Friday night, I was watching Colby's rabbit and had big plans of watching her DVR and eating a healthy meal.  I played a Word after polishing off said healthy dinner, and immediately got a text from WIMB!

what are you doing playing words instead of drinking?

Oh no. I'd been caught.  I truthfully said I'd just finished dinner, and tried to figure out how I'd play this.  He semi-invited me to go drink with him and his buddy, who'd be leaving soon.  I went back and forth on whether I'd accept his half-invitation. Eventually, frustrated with how DAMN long we'd been interacting before the chance of hanging out would come, I drove down.  He was clearly even more shitfaced than he'd indicated. So I decided to try and play catch up.  At least WIMB is a decent enough human being to pay for drinks.  His friend showed up unexpectedly, so I bonded with the friend's 19 year old lady friend.  Add this to the list of awkward moments.

So the bar starts closing and I agree to drive WIMB back up the hill to his apartment.  Of course I followed him inside, where I saw his assortment of sporting equipment.  He had everything from a bike to golf clubs to skis and snowboards and hunting gear and soccer cleats... Sexy. So I grabbed his tri-suit top, threw it on, and had him put on his American-flag print bike jersey.  We started making out on his couch, made our way to the bed and... well... I woke up the next morning and let's just say I was no longer rocking the triathlon top.  WIMB was sweet that morning, even shutting the blinds when I complained of darkness. We messed around again and snuggled until he determined it was time to get up.  I drove him back to his car and we pecked goodbye.

So clearly I was having mixed feelings about this little interaction. But after months and months of miscellaneous banter, I decided it was bound to happen. And to let things run their course. We'd still talk via IM but our in person interactions had not improved. He certainly wasn't asking me out. And I was convinced he'd gotten something from me and was done.

Fast forward to one year later. I still crushed on WIMB pretty hard, but knew he was a lost cause. Cute, but a bit too shy and apparently a closet player! WIMB chatted me up and asked me if I'd play on their local soccer team. I agreed. But it turns out I was never needed. Either way, it sort of re-opened the doors to our virtual flirtation...Luckily since we'd finally exchanged numbers it extended from Work IM to Text Message.

Anyway, I kept my distance but was a bit chattier at the gym with him and decided I'd stop trying to impress him and just be me. I spotted him at a bar another Thursday night. But he didn't see me. So I decided to text him and see what happened.

He expressed disappointment, and thus began another evening of back and forth and inviting me to go to the bar he was at (alone... Alcoholic much?).  Anyway, our casual happy hour turned into shots of Jameson with colleagues from across the pond, chugging too many beers and a very late night. WIMB was asking me to go to his apartment.  I told Colby and she was all for it, even calling me a taxi since none of us were in any condition to drive.

I arrived, WIMB having left the door open to his apartment building. We immediately started hooking up, but had some minimal conversation. I asked him if he really was that shy - since he was cute and always out and about.  He said yes, which to this day I find a bit confusing. He definitely seems to hide behind phone and computer screens and/or use his liquid courage.  

Anyway, I refused to have sex with him. He was not too happy about this but I think we enjoyed ourselves anyway.  He drove me to the train station and something told me that was the last time we'd enjoy such an interaction. The next day, I was forced to apartment hunt in the same clothes I'd worn to work the day before. Talk about a walk of shame!!!

Rumor has it that now he's sleeping with a married chick, who we shall call the Maneater. And yet I wasn't interesting to him? I've since decided that I was too much for him... I didn't fully give into his charms, after all. I'm smart, fun, and independent. He even thinks I'm athletic. And although I'd sometimes make the first move, I kept a fair distance and tried to be playful... Despite the fact that he was frequently the only guy I found interesting. I realize now that our frequent IM conversations were probably just to pass time during work.  They had nothing to do with how awesome or awful I am.  I will admit that I still wonder if I could have changed things- would we be dating if I didn't give in almost two years ago? Or would we still just be randomly IMing about biking or drinking?  I still think he's adorable and try to walk a bit more confidently when I know he's around.

Bridge Theory

If a guy wants to be with you, he will build a bridge to get there.

-My Wise Friend Mrs. S.

City Slicking

Well, kids. I'm officially a New Yorker.  This means a gazillion single men and way too many nights at the bars.  I will say that over the past couple years, I have changed my behavior tremendously. I steer clear of blacking out and having one night stands.  I try to have a bit more discretion and avoid public makeouts at (almost) all costs.  That said, I do frequently have bizarre experiences with the opposite sex so I figured I may as well document it. I have so many questions, yet so few answers.

Let's start with a few recent examples:

• My Sunday Funday turned into a dinner date, followed by Pawn Stars on the couch with a bottle of Pinot and laughing with my roommate. He never called.
• Closing down the bar with a guy who thought I was familiar at the gym, and a quick (but pretty good!) kiss good-bye. He never called.
• Talking to a guy who lives in Indonesia at the bar last night. He told me I was a very attractive girl and he was surprised I was single (??), then asked my my long term plan. And why I didn't want to get married soon. I said I wanted to make money. He legit RAN away.
• Guy who told me I was just his type and monopolized a solid hour of my time at the bar. And never even gave me the courtesy ask for my phone number.

Nothing out of the ordinary of course. Just the typical highs and lows of being single in the City.

The Shy Guy

I work at a big financial firm. One night, after using work-owned seats to go to a Rangers game, Colby and I were on the train home. Out of breath and hunting for seats, we walked the aisles until we found a nice open area where we could put our feet up. We walked by a lone cute guy and I stopped, turned around and said to this guy, "Wait!" and yelled the name of our employer. He laughed and said yes. We sat in the row near him and chatted for a bit. Colby passed out, and me and this guy chatted until he got off the train.

The following Monday, I sent him an IM (from 20 feet away) asking how the rest of his weekend was. He said good, etc but that was pretty much it. We'd say hi if we passed each other in the hall or the cafeteria, but otherwise nothing came of our little train conversation.

A month or so later, I moved three floors away to a new job. About a week after my big move, I got an IM asking where I went from my train friend! We started IMing... and then it turned into IMing everyday for a week. And he next week. Even though it was over IM, he made me giggle at my desk and we had a lot in common. The first time we encountered each other in person, it was incredibly awkward and we tried to chat but we were in a loud and crowded cafeteria. I was signed off of IM, so he shot me an e-mail and we went back and forth for a bit. But that's pretty much where it ended.

I was hoping to encounter him at the company Christmas party so we could chat in a more relaxed environment. Unfortunately, he wasn't signed onto IM all day and was not at the bar. Disappointment. I decided to back off for a bit, since clearly this wasn't going anywhere. I was hoping he'd perhaps try to meet up somewhere or somehow but I guess...not.

Like 85% of the world, "Work IM Boy" as I affectionately call him was on vacation the week between Christmas and New Year's. The first Monday of 2011, I saw him in the caf and said hello. Minutes later, I got an IM asking about my New Year. And the chatting began again. Sometimes, I'll shoot the first IM. Even if we encounter each other in the gym or else where, I have a feeling he won't make a move. And there's not much else I can do. The only way we'll ever get beyond the IM is if one of us chats up the other in real life and tries to hang out outside of the work building. And I don't think it's going to be me. It's really too bad, because he's cute. But I wonder if he's just not interested or that shy?

Sketchy Steve

Back in July, I met a guy at the bar with Seraphina. He was cute, smart, well dressed and a law student. Seemed to be a nice enough guy. His friend TR joked that Steve often went missing, which I immediately used as reason to dismiss him. But he assured me that he'd come around for me. So we exchanged numbers and he actually called me a couple days later. But we never got together and he quickly faded into the background.

While Colby and I were at the Rangers game sometime in mid-October, I got a text from a random number. When I opened the text, I realized that it was that guy from back in July, asking me if I was out at the bar where we met. I was kind of drunk and responded enthusiastically, instead of ignoring the text like any smart girl would. So I heard from him a couple days later and agreed to meet him for a drink. And I even managed to remember his name before we met up.

We met up on a Thursday night and actually had a really good time. Somewhat suspicious, I joked around but was not overly bubbly. We had good chemistry, and of course he talked about doing things together in the future (a game I will never quite wrap my head around). He kept his phone out on the table, and I noticed someone with a gender neutral name called him twice during our date. Hmm. He mentioned a friend's party that following Saturday and invited me to potentially join him. I told him maybe and figured he might just go missing again. But since I'd had a good time, I tried to think positive.

Surprisingly, he invited me to go out with him and his friends that Saturday. I called up Elena to join me and we planned to head up to meet them at a bar in his town. I last heard from him around 9:00 PM while still getting ready. He was at his buddy's and said he'd let me know when they all headed to the bar. I dolled myself up and put on a fitted sweater, leggings, and 3" ankle boots (Steve is not that tall). I was feeling pretty and confident and curious about how the night would turn out.

So I zoomed over to Elena's and we decided to have a drink since I hadn't heard from Steve. One drink turned into two, and by 11:00 we decided to just head to our usual stomping ground. I thought about contacting Mr. Sketchy, but I was annoyed and figured it wasn't worth it. Elena and I ended up having quite a crazy night anyway. Oddly enough, I got a text from Sketcher as the bar was closing - saying "what's the matter?" then soon after "sorry that was for someone else"... So I said no worries and he said he'd wanted to see me that night. Well, I had zero information, idiot. The game continued, he contacted me the following weekend and asked me what I was doing on Halloween. As if I wouldn't have plans. And then asked me to meet him and his friends at the bar the following Friday.

For some reason (boredem? desperation?) I decided that despite his blunders, I'd meet up with him and his friends. On my own. I chatted a lot with his friend TR and we had a blast. He was all over me, and kept trying to smooch me. I think he was drunk...(perhaps because of the car bombs we had?) which makes everyone a bit more friendly. I realized that we could party together and hang out and just talk. And he was introducing me to his friends girlfriend and his friend from work. Whoa.

Then he went missing again. We'd exchanged gmail addresses, and he g-chatted me a few times, saying he'd be down to grab drinks in a few weeks. A few weeks? Really? When you've been missing for the past month? No thanks. So I was cool to him and decided to just give up on Sketchy Steve, since obviously he didn't think I was worthy of his time. I realized that I should adopt the same attitude.


Christmas night Janelle called me and we decided to meet up with some friends at the only bar open on the holiday. So while we sipped on our first drink, in walked none other than Sketchy Steve! I said hi and he went on his way, only to return numerous times throughout the night and just kind of....stand there and stare into my eyes. Janelle did a perfect impression - he came in from smoking a butt, beelined to me, and just stared! I tried talking but he seemed completely uninterested in such matters... It was quite odd. When I was kind of tipsy and being silly, he said he "liked me like that".... I told him I'm always silly but he had trouble believing me. I guess I'm more guarded and bitchy than I thought. In any case, I tried to be friendly and was generally confused by this fellow.

So I think Sketchy Steve - six months later - is a lost cause. I tried to be myself and still play hard to get - I didn't want to just give in and act like I was super into him. Even though I was enjoying myself...I wasn't just going to make the first move and accept every invitation he threw my way. He wants to get drinks once every few months, that's cool. But I'd rather he didn't pretend as if he is super into me when he pops up at the bar. Then again I suppose creepily staring into my eyes isn't necessarily him being into me. But now that we're connected on g-chat and facebook, he's just going to pop up on chat lists and remind me of his bizarre form of prolonged rejection.

Holiday Reflections

Christmas Eve is big in my family. My aunt and uncle do a huge fish feast and theres fifty or so people eating, drinking, and being merry. Anyway, my cousins and I reconnect and there is always the ever present question: "Are you dating anyone" or "Are you still with that accountant?" or (my personal favorite - from my divorcee cousin) - "Nice seeing you, Merry Christmas. Next year you better bring a boyfriend!"

Seriously?

I'm TWENTY FOUR! And as much as I love and appreciate my family, I'd have to be very serious with someone to brave bringing them around my loud and opinionated family. It's almost tempting to lie and say I'm dating someone fabulous. But I'd feel like I was jinxing myself if I did that. I just don't get it - can't my new job count for anything? My fabulous outfit? Giant tray of baked goods? I suppose it makes sense, I never bring anyone around. But I'm young! And I told them all how I have a great time. I am certainly looking for someone or something more that what I've had in the past. But I can't force it.

My uncle even asked me today if I'd tried online dating (since he lacked success in the area). Do I reek desperation? Okay, so perhaps I'm yearning for a bit more than I once was. And I'm not entirely fulfilled by my party lifestyle. But I'm not ready to just jump into something with a stranger met on the internet, either. I'm not really sure what I want. I'm not exactly meeting new guys every night. And when I do, it's not very often that they ask me out. And if they do, they certainly don't stick around for very long. I'm not sure if I'm missing the memo somewhere, since I just float through and try to think positive. Maybe I'm boring. Or perhaps its my inability to open up. I don't know. But I sure don't enjoy being reminded on Christmas!

Cock Boy

One night, Colby and I went to a Rangers game. Following the game, we wandered off to a couple of bars. Around the time we got to the second bar, I was +/- seven beers deep and quickly wandered off to the ladies room, where I proceeded to take a nap.

A short while later, I awoke somewhat refreshed and found Colby smooching a young man. She introduced me, but having been up since 6:00 am, I began to doze off while attempting the usual small talk. I was glad Colby was having a good time, and also found this Bro J's barstool uncannily comfortable. Soon after locking lips with this guy a few more times, Colby informed me that we had to run to catch the last train home. In the cab ride over, she told me all about this new boy and what a great conversation they had. They had similar interests and the best part was that he was from San Diego, where Colby lived for a few years after college.

A few days passed, and I asked Colby if she'd heard from "that guy she was making out with at the bar". She said that they'd been doing some texting and she perhaps wanted to meet up with him in the city on Halloween night. I was also planning to be in the city, so we made plans to go in together. Colby had been texting with San Diego on and off for the weeks in between, and told him she'd be in the city for Halloween. We began at a bar somewhere downtown, easing our way into what would surely be a long night.

Well, when it was nearing mid-night and I'd finished my second Red Bull vodka, I got really antsy. I told Colby I wanted to go see Kendall and Maura in Midtown, and it was getting late! Colby asked for 10 minutes to see if San Diego Boy was going to text her again. Having little trust in random guys met at bars (for many obvious reasons), I began to doubt that this dude would actually appear.

Surprisingly, he did! Unable to find a taxi, we walked blocks upon blocks to a party to meet him. When we met Mr. Coming to America himself, he turned out to be quite nice and the party was a blast! It was like college, complete with giant tupperwares filled with ice and canned beer and a sketchy bedroom for "secret" activities. I let them bond while fiending drunk dials from Elena, letting Colby get to know this fellow from the bar. Eventually, we decided it was time to move onto our next venue. Colby made plans to meet up with him later that week after he finished a mid-term.

When she texted him a few days later, asking how studying was going, he replied to her with the below, saying "thinking of you":

What a lovely way to say hello!

Thanks for the Thanksgiving Wisdom

My great aunt was happily married to my grandmother's brother for +/- forty years until he died. Still a spitfire (with an immacualte home) at 80, she asked me on Turkey Day if I have a boyfriend. Obviously no. And asked if I get asked out a lot.

I grimaced and thought about the last time I was asked out. And how he, like most others, went missing.

"Rarely." I said.

She looked at me, then to my mom, and said "Maybe you don't have the right approach." Before I even had time to react, my cousin's girlfriend chimed in and said something about how pretty girls have a hard time because guys are intimidated. I always find that this is bullshit, since my much-prettier friends have zero problem getting asked out. I laughed saying that I also have a mouth. My cousin's girlfriend smiled and the subject was dropped.

My great aunt's comment really got me thinking. She was happily married, and I imagine was quite a "looker" 55 years before. Maybe I don't have the right approach. I mean, on my way to and from work, I rarely smile. Actually, I don't really smile much at all. That would probably be a start. And when I do meet someone new, I act completely uninterested...Even when I am. It's that whole guarded thing again. I try to heed Janelle's advice and take down my emotional wall. Part of it might be because, no matter how many compliments I recieve, I've never thought of myself as pretty. Yeah, maybe I'm okay. Whatever. My roller coaster of jobs since college plus recently gaining back the fifteen or so pounds I lost in the time since I graduated hasn't exactly made me feel very good about myself. Maybe I appear negative and people (guys) notice. Definitely not the right approach... But I don't really know what to do to make my approach the right one...

The Gentleman Caller

Janelle always manages to forge new "relationships" and talk to new guys before ever really well, meeting them. Facebook poking to her is what the wink is to match.com users (if I am correctly informed). Typically, they are friends of friends who she thinks are cute. No matter.

This time, an acquaintance messaged her and asked to hang out. They went back and forth with Facebook messages, then he asked for her number.

A couple days later, a number just one digit off from her own phone number blew up her phone. Thinking it was a prank, she ignored it.

But it was not a prank. It was him! He actually called! And has continued to do so, asking how her day's been and such. Adorable. Yet so rare these days! The last guy to call me was the accountant, and before that.... I have no idea! We've all become so lazy and rely solely on text. If a guy won't call me, I'm not going to just up and call him!

Have our expectations become so low that a guy who calls is that incredible? I mean, I suppose it's a nice gesture. After all, a call implies he's really thinking of you. When he's texting, he could be contacting four other girls at the same time (and saying the same bullshit). But the calling. It really makes you feel special. The guy is really putting in some effort. Hopefully Janelle has some great luck when she actually goes out with the gentleman caller this weekend. We'll see!

Satisfactory Singledom?

This weekend, we had an absolute blast for Janelle's birthday. Open bar and a dancefloor: I was in heaven. I frolicked around with the girls and, despite my throbbing toes, boogied the night away. Now, there were plenty of new and eligible bachelors. However, I had no desire to talk to or dance with any of them. I just wanted to do me. So, I kind of wandered away if a guy approached me and just hung out with the girls. I must admit, Sunday I got a little sad. Perhaps I should have given that short, annoying guido a chance. But he had taken full advantage of open bar, and I was still sober enough to feel my feet hurt at 3:00 am.

In any case, I think my slight sadness on Sunday was due to too little sleep and even less to eat. But afterward, when chatting with my friend Chaz (who's in love with Seraphina), he asked me "which of his friends I wanted to sit on". I thought about it, and no one came to mind. Among his friends or otherwise. Oddly enough, Cornell popped into my head over the weekend, but it was fleeting. I've been on a couple dates with a guy I met, but I'm not sure I'm feeling him. I think I'm becoming okay with the way things are. I have about ten pounds to drop (again). Maybe once I feel less like a linebacker (and more like a PYT), I'll be more willing to hookup or even seek a relationship. But for now, I'll crush on the new guy at work and focus on dragging my (ever expanding) ass to the gym a LOT more often.