A New Beginning Pt. 01

"Well duh...I didn't want you to get too thin and start to wither away." He retorted, "By the way, I know you were waiting to lose weight before getting out there in the whole dating game thing, but 100 pounds down is pretty substantial weight loss. How low are you trying to get before you're ready to be my wingman? I could have used you this past weekend."

"I dunno, I still feel kinda chunky. I'd like to get down in the 220s maybe? The ultimate goal is obviously still 215, but I think in the 220s I'll feel like I'm not a fat slob anymore."

"You're not a fat slob now. You're skinnier than like 70% of people walking around. But whatever you wanna do man. We should start weighing in every week since it's getting down to crunch time."

I agreed and we left the gym to shower off with me feeling pretty good, but a little disappointed. It would be another 2-1/2 brutal weeks before I finally hit the 100 pound mark which Wes and I went out and celebrated with after work drinks.

By the time I was down to 220 pounds there was very little evidence that I'd ever been overweight. Sure, I had a few stretch marks here and there, but overall that was about all that was left of my former self. My parents couldn't believe my transformation and wanted me to send them pictures as often as possible so they could hang them around the house and show everyone the new me.

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It had been weeks since I'd been into the 220s and I knew Wes was going to bring it up at some point, but I wasn't sure if I was ready for the dating scene yet or not. We were out for drinks after work one Friday when he finally approached the topic.

"Ok, you're lookin slick, you got the clothes, you got the body, you're all primed and ready for wingman duties, wadaya say? This weekend? You and me, out on the town, chat up a few lovely ladies?"

"You act like it's just that easy. See girl, talk to girl, girl and guy ride off into the sunset. I haven't done anything like that in...well...actually I've never done that. I'd feel like such a creep just walking up to a couple strangers."

"Well when you look at it like that then yeah, it seems daunting, but what's the worst that could happen? They say no, you walk away and grab a drink at the bar with me. Big whoop, happens to everyone."

"Yeah, for Mr. Smooth over here I'm sure that works. I'll be lucky not to get maced and kicked in the balls."

"Haha oh c'mon man, it's not that hard. Just don't be creepy. If you're nice and show a genuine interest without being pushy you'll be fine. If she says no, back off and don't push it. That's all there is to it. That girl, right there, go talk to her." He said pointing to a stunning blonde sitting with a friend by the window.

"She's busy. She's with a friend. I'm not going to interrupt."

"Oh so you only talk to women that are sitting in a bar at night totally alone? Good plan. So do you want to give me power of attorney for when you're alone in the nursing home now or later? Cuz you aren't ganna find anyone with that strategy." Wes prodded.

"God damn you and your logical ways." I acquiesced. "Fine. But not her, they look busy."

"Oh for fuck's sake! I'll go with you. You take the blonde, I'll take the brunette. Happy?"

"No...but I'm rarely happy when I'm with you so that's not a new symptom."

"Hardy Har Har, let's hope she finds wallowing in your own sadness attractive." He said as he pushed back from the bar and waited for me to do the same.

I took a deep breath and prepared myself for the inevitable disaster. I followed Wes over to their table and let him take the lead.

"Excuse me, we're very sorry to interrupt, but we were wondering if you ladies would let two idiots buy you a drink?" Wes asked.

The brunette smiled and glanced at her friend, the blonde looked back and a conversation passed between their eyes before the brunette replied a moment later, "I don't see why not! Thanks!"

The blonde looked as if she had lost their nonverbal discussion, staring at her friend with a slightly annoyed expression.

"Great! Well what can we get you two?" Wes asked.

"I'll have a margarita on the rocks, light salt on the rim." The brunette said, then looking to her friend.

"I think I'll do a bourbon on the rocks. I'll let you pick the bourbon." She responded with a smile tickling the edges of her lips.

"Sounds good! You won't be disappointed, Jason loves his bourbon so I'm sure he'll have something good for ya." Wes added before heading to the bar.

"Oh lovely, no pressure at all now!" I said, rolling my eyes as I turned to follow him. The girls laughed as we walked away and leaned in close to obviously talk about the two of us.

"Ok master distiller, what's the move?" Wes asked. "Don't go too crazy here, they could just be using us for a free drink, so don't blow your bank account on something fancy."

"Wait, girls don't like when you become destitute after buying them one nice drink? Do go on sensei." I joked as I read through the bourbon bottles on the shelf behind the bar.

"I'll do 2 Willett's, one on the rocks, one neat please." I said to the bartender.

"And I'll do a margarita on the rocks, light salt on the rim, and a captain and coke." Wes called to another bartender.

"Ok so...what's the plan?" I asked.

"Plan? There is no plan. Just talk, have fun, be yourself. You'll be fine."

"Ok, well, here goes I guess." I said as we carried the drinks back to the table.

It went fine. I was clumsy and awkward, as expected, while Wes was smooth and charming. He probably could have gotten the brunette's number if I hadn't held him back, but overall it wasn't the worst first attempt.

Over the next few months Wes would unexpectedly get up at random points during our night out and force me to accompany him in talking to random women. Eventually I became more comfortable in the endeavor and didn't see it so much as flirting as just humoring Wes.

One such evening, in the middle of me telling him about a particularly shitty meeting I'd had earlier that Friday, Wes stood up. I stopped mid-sentence as he grinned like an idiot and nodded his head toward two women sitting alone at the back of the bar.

"Seriously? Mid thought now? I can't even finish my rant?...Fiiiiine, let's get it over with. Do you know how much money I've dropped on these little escapades by the way? It's enough to get us both plastered drunk for a solid week or two. Which one do you want?" I asked, exasperated.

"I'll take the redhead, she looks fun."

"Fine, I'll take the brunette."

As we walked over I took a good look at the girl I'd had selected for me; she was very attractive with cascading dark brown hair that ended just below her shoulders, soft grey blue eyes, and a brilliant white smile that made her eyes squint as she laughed at something the redhead had said. She had a friendly face that helped ease a little of my anxiety. She was clearly in good shape, wearing a tight fitting dress that showed off her flat stomach, skinny waist, and emphasized her ample chest all while ending short enough to show a set of long toned and tan legs. She was out of my league for sure, maybe not Wes', but she was definitely a 9 or 10 in my book. Thankfully, Wes had consistently put me in the position of talking to women that were way above my caliber so I'd gotten used to the feeling of inadequacy from talking to a gorgeous woman.

"Excuse me ladies, sorry to bother you, but would you object to two losers buying you a drink?" Wes asked. He always had the same introductory line with a slight modification as to whether we were both stupid, inept, losers, or struggling, but it was clear why he went with it, it worked. Nearly every time the self-deprecation elicited a smile, and 75% of the time they let us buy them a drink. This time was no different.

"Well hello losers." the redhead giggled, "I suppose I'd be open to that. Wadaya think?" she asked her friend.

"I guess so." the brunette answered, slightly less enthused.

"Well what can we get you two?" I chimed in.

"2 more gin and tonics?" The redhead asked her friend.

"Works for me." the brunette responded.

"Great! We'll be right back." I said smiling at the brunette and hoping she didn't feel like she was getting the sour end of this deal.

We went to get the drinks and casually watched from afar as the two women talked animatedly back and forth. The redhead looked excited and happy about the whole scenario while the brunette seemed less so, but content to go along with her friend.

"Here you go. I'm Wes by the way." Wes said as we sat down, delivering the drinks and offering his hand to the redhead.

"Nice to meet you. I'm Alice."

"Nice to meet you Alice. And you are?" Wes said, turning to the brunette.

"I'm Kate. Nice to meet you."

"I'm Jason. Nice to meet you both." I said as I shook their hands.

"So are you guys out celebrating anything special or just out for weekend drinks?" Wes asked

"No, nothing in particular. Just wanted to get this one out of her apartment for a while." Alice said, nodding towards Kate.

"What's so wrong with being a hermit? I like my alone time, that's all." Kate protested.

"Haha well getting Jason out is like pulling teeth so you guys can talk all you want about how lovely silence and seclusion are." Wes laughed as he turned to Alice.

"So, fellow loner, what do you like to do with your free time?" I asked Kate.

She smiled, "Oh ya know, the normal stuff, Netflix, random movies and TV, I play a few video games, and just enjoy not having to talk to people."

"Well I'm sorry for putting you through the agony of a conversation. So you game a little? What are you playing right now?"

"It's ok, it's good for me to at least talk to someone every now and then I guess. Right now I've mostly been playing the new Final Fantasy. I used to play them a lot with a friend in high school so it's kind of a nostalgia thing."

"Haha hey we're in the same boat. The only reason I'm over here is because Wes keeps forcing me into being his wingman which I guess is good for me since I wouldn't do it on my own...not that you aren't worth it or anything...sorry, I didn't mean for that to come off like you weren't worth walking over for, you're beautiful...sorry -"

"Haha its ok, really, I know the feeling. And thanks." She said bashfully.

"Ok good. So Final Fantasy huh? I haven't played the new one but I used to play them all the time. Is the new one any good?"

"Yeah it's alright. I mean, I'll always like the old ones better just because of the whole 'longing for your childhood days' type thing, but it's not a bad game by any means."

"I'll have to check that out."

"So what do you like to play?"

"I jump all over the map. I'll sit around and play old N64 games, new RPGs, occasionally I'll get on a sports kick and play out seasons and that sort of thing, but mostly I just like sitting there and not thinking about anything else for a while. It's sort of like the lazy person's meditation or yoga."

"Right!? That's the perfect description of it! I've tried explaining it to Alice but I haven't been able to find the right way to convey it. I like that though, it's the lazy person's meditation."

The conversation continued and seemed to be going really well. We had a lot in common and nothing seemed forced. There were even lulls and quiet points in the conversation when we had exhausted a topic and not found a new one where the silence would normally have been awkward, but with Kate it seemed natural. As we talked, I learned she was a Vet Tech for a local animal hospital. We both agreed that we'd love to have a dog but New York City wasn't the most pet friendly place, nor did either of us have an apartment large enough to accommodate one.

Wes and Alice had been a nonstop flood of conversation across the table and were clearly hitting it off. When the lights flooded the dark bar and the inevitable disappointed groan died down from the crowd, we all looked at one another, waiting to see what the others wanted to do.

"So, would you guys like to keep the party going?" Wes asked finally.

"Sure! What'd you guys have in mind?" Alice responded with more vigor than the hour probably warranted.

"Well...which direction are you guys going to get home? Maybe that will determine our next destination so we don't drag you girls too far from home."

"We're both about 5 blocks north of here."

"Ok, well..." Wes looked at me, trying to convey what he was thinking and get me to suggest it.

"My place is only a few blocks northeast of here. We could go hang out there for a bit. I've got beer and liquor and board games if you're interested." I said, getting the hint from Wes.

Alice didn't seem too keen on the board game idea, but Kate perked up.

"Ooo! I haven't played board games in forever. I'd totally be up for that!" She responded excitedly.

"Ok well let's head that way and you two can play board games til your heart's content while Alice and I watch old MXC youtube clips." Wes suggested.

"Oh my god, YES!" Alice exclaimed; apparently it had been something they were talking about throughout the night.

We all got up and filed out of the bar. Alice clung to Wes' arm as they happily bounced down the sidewalk in front of Kate and me, jabbering about old MXC episodes they'd seen some years back.

The dichotomy between our two pairings was almost comical; Wes and Alice clung to one another, playfully pushed and flirted, talked nonstop, and were without question having a great time together. Meanwhile, Kate and I were having and equally great time together, but walked separately with looks of calm contentedness on our faces, speaking softly to one another, and enjoying a few quiet moments.

"That's just exhausting to watch." I said quietly to Kate, nodding towards Wes and Alice.

"No kidding. I don't think I could keep up that level of energy for an hour let alone all day like she does."

"Haha Wes is the same way. He doesn't even drink coffee. I think he's a psyborg; it's the only rational explanation."

"I told Alice she reminds me of a 6 month old puppy. She's past the stage where she falls asleep after short bursts of energy like a 3 month old, but she's got a never-ending motor that will inevitably lead to her biting someone. Thankfully she doesn't bite THAT hard."

"Hahaha wait...why does she bite at all?! Should I be warning Wes of something?" I asked.

"Haha no, I imagine if she's biting him they'll be in a position that he's reaaaallly not going to mind it at all." Kate replied with a raise of the eyebrows.

"Ahhhh...that kind of biter. Yeah, then she can probably bite him as hard as she wants and he won't stop it. Wait...how do YOU know she doesn't bite that hard?"

Kate blushed fiercely, "Oh...uh...ya know...just a night of a little too much to drink and a long time of feeling lonely I guess."

"Haha ah, ok." I said, taking the hint that it probably wasn't a subject worth pursuing.

Alice and Wes stopped outside my apartment building and let me push past to open the door. We entered my small studio apartment and I offered everyone a drink as Alice and Wes sat together on the small sofa and Kate sat on the foot of my bed. I made drinks for everyone and started to gather up a bunch of my board games for Kate to choose from. Before I had gathered them all up I felt a hand on my lower back as Kate knelt beside me and grabbed the game Dominion off the bottom shelf.

"I can't believe you have this game. We're definitely playing this. I used to love this."

"Really? Not many people have played it! I love that game but it can take a little time for people to learn so it's not often I get to play it! Let's do it!" I said, excited to play a game I hadn't played in years.

Over the next hour, Kate and I set up and started a game of Dominion and were thoroughly engrossed when Wes and Alice finally ran out of MXC videos to watch; or at least that was their excuse for saying they were going to get going. I looked at Kate, expecting her to leave with Alice, but desperately wanting her to stay.

"Aww, we're right in the middle of the game! Can you wait like...wadaya think, we might have another...half hour?" Kate pleaded.

"Yeah, maybe, maybe a little more, depends how things play out." I answered.

"I'm pretty exhausted." Alice said, "It's almost 3."

"I mean...we could always finish this game and then I'll walk you home." I suggested, throwing a hail mary.

There was a pause as everyone glanced around at one another, the girls looking to each other trying to assess whether that was a safe option since they'd just met the two of us.

"I promise I'm not a creep or anything, I really will walk you home." I tried to justify before realizing I'd probably made it worse, "I mean...you can go if you want to, it's entirely up to you. We can finish the game some other time if you'd prefer."

"No, let's finish now. It's fine." She said reassuringly to Alice, "I'll be fine. I'm only like 2 blocks away."

"Ok!" Alice said in a chipper voice that said there was no way she was actually exhausted.

"I'll walk you home then." Wes said to Alice as they pushed off of the couch and headed towards the door, Wes' arm wrapped around Alice's waist.

"Thanks for all the fun, and take good care of her Jason! Kate, text me when you make it home, k?"

"Yes mother, I know how you worry." Kate retorted, "I'll call you tomorrow at some point."

"Sounds good!" Alice said as she skipped out the door.

"See ya man, talk to ya tomorrow. Nice to meet you Kate, and have fun with whatever you're playing." Wes called.

"Later!" I yelled as the door closed behind him.

Kate and I turned back to our game and the room fell silent. We spent the next 45 minutes barely speaking, just analyzing our cards, figuring out what our next move would be, and trying to determine what the other person was going for. Eventually the game ended with Kate exclaiming, "Boom!" as she threw down a few cards, showing she had won, "Victory is mine! Great game though! That was so much fun."

"Haha well I'm glad you had a good time. We'll have to play again sometime so I can try to get a revenge win."

"You can try, but no promises that you'll ever get it!" Kate teased.

"Well, should I walk you home? It's almost 3:45."

"Holy crap, I haven't been up this late in a long time. Yeah, I should probably get going." She said standing up, "You don't have to walk me home, it's only like 2 blocks away."

"It's ok, really, I'd feel better knowing you made it."

"Well thanks!" she said, slipping her shoes on as I did the same.

I walked to the window and opened it a crack, feeling a cool breeze rush into my apartment. I walked over to my dresser and grabbed a large hooded sweatshirt out of a drawer.

"Is it that cold out now?" Kate asked with a look of concern on her face.

"Yeah it's supposed to get pretty chilly tonight. Here." I said handing her the sweatshirt, "Throw that on, it'll keep ya warm."

"Aww really?! Did you seriously just check the temperature to see if I would be cold in my dress?"

I felt the heat flush my cheeks, "Maybe..."

"That's so nice! Thank you!" She said, giving me a quick peck on the cheek. I blushed even harder.

We left my apartment and I let her lead the way to hers. We made small talk as we walked but I was only half paying attention. My mind was racing trying to figure out what I should do when we finally got to her place; do I kiss her? Do I just say goodnight? Do I give her a hug? No, definitely not a hug, that's definitely instant friendzone for sure. She did kiss my cheek, does that mean she likes me? Was it just a thank you peck? Shit! Why am I not better at this!? Ok, if I try to kiss her and she doesn't want it, that's it, it's over. If I say goodnight and just leave, then maybe I'll have another shot in the future. Ok that's it, just say goodnight and leave it at that.