[MF] My once in a lifetime, what-if opportunity with the girl of my dreams [long] [part 1?]

I’m finally at a point where I can talk about this without going insane. Here’s my will-they-or-won’t-they story that I’m writing now given some inspiration from some awesome posts these past weeks. I’ve actually had this written for a while now but never submitted. All of this insanity ended around three months ago.

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I lead a small team in a finance company in the US. 32, 5’11, 190lb, I enjoy the outdoors but I’m certainly not fit or athletic. I’d give myself a 6/10, 7/10 if you include the cuteness factor (I’ve been told I’m a very lovable person). Kelsey joined my team about a year ago and started adding immediate value to a couple of projects I was having a hard time pushing on. She’s smart and a dedicated worker. She was also fine as hell. 25, 10/10. Half French, half Japanese. Tall, shoulder length black hair, slim but with crazy curves above and below the hips. She also had the most mesmerizing big, brown eyes with an elegant nose and pillowy lips that were on the cute side of pouty. When she smiles or laughs it’s genuine and you can feel her warmth and honesty. She was just a person you could hang out with and she would make you feel like the most interesting person in the room. Can you tell how head over heals I am? From a distance she reminds me of [Kristin Kreuk](https://www.supermanhomepage.com/images/smallville/season2-04-lana.jpg).

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The trouble started a couple of months after I hired her. We had just wrapped up one of our monthly 1-1 sessions and were on our way out when she paused at the door. I could tell she had something to get off her chest but was hesitating. I invited her to sit back down and talk about it. After dancing around the subject for a bit she finally opened up and told me that her boyfriend of several years just proposed this morning and she accepted! I felt like a congratulations was in order but something didn’t feel right. She continued, saying that he didn’t technically propose he just mentioned that they should get married and asked her if she agreed. He wanted to propose and was going to do it after their hike that afternoon but just blurted it out prematurely. He didn’t have a ring or any sort of proposal speech. I knew Kelsey wasn’t a die hard romantic, but I also knew she was expecting more than a half-hearted attempt when being asked to spend an eternity with someone.

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And so began a series of pretty lengthy therapy sessions. For me, it was an excuse to blow off work for a while and I certainly didn’t mind spending more 1-1 time with Kelsey. We bonded in a strange way over her relationship issues and I also opened up about my previous lack of success. We spent more time on and off the clock hanging out. We talked about the most random things and pondered the meaning of life and why the universe was out to get us. During that time I felt like we become much closer friends but that was it. There were no stolen moments or drunken mistakes. She just became my “work wife”. Looking back, this sequence of events was certainly suspect but at the time I was just living in the moment.

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Then came the business trip. There was a yearly, week long conference in Chicago that my company attends and this year she and I had signed up to go. This was determined months before our 1-1 sessions so at the surface everything was above board. But the lead up was brutal. A couple of weeks before the trip we started talking about all the foods we wanted to eat. She was a big foodie and so was I and we commiserated over the fact that our friends did not enjoy food as much as we did. We swapped Yelp links and reviews of fancy restaurants. We jabbered excitedly about all the things we were going to eat and do. We oo’ed and ahh’ed over each other’s shoulders and exchanged hushed giggles. It felt to me like subtle, teenage flirting. My heart fluttered when we got close and rubbed shoulders, when we were pointing at the screens and our hands touched. My stomach dropped when I caught the scent of her hair and when she looked at me with those endless eyes. When she smiled I would lose my words.

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I was drawn to her. I wanted to spend every waking moment with her. But I couldn’t. So I bottled it up and pushed it away. I relegated myself to be a great friend who helped her with her relationship issues and who shared her excitement over food. I convinced myself these butterflies were not reciprocated–I was wrong.

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It started on the very first night. We flew in and checked into our hotel rooms separately and texted to make dinner plans. Nothing special, just a pizza bar down the street. We walked there hurriedly, excited to be in the city but with our hands on our pockets from how very cold it was–when I exhaled it looked like I was vaping. The pizza was ordinary, deep-dish and we both had a single bottle of beer. We chit-chatted about our travels and the weather and the conference–everything was normal. But when we paid and left we realized it was still pretty early in the night, 8pm. Why go back so early? We Yelped and found a roof top bar nearby. Sure, why not?

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For 8pm, the bar had a decent number of people in it and thankfully most of their large space was indoors and heated. We ordered drinks, sat down, and just started talking about the most random things, all the foods we were going to eat, all the notes we were going to take, all the walking around we were going to do. As the drinks kicked in the conversation changed. She talked about things that her new fiance didn’t like to do–sit in bed and watch a movie, put on face masks and make funny faces, talk intelligently about life… I was drawn in. As we talked I kept picturing me in that position, doing those things with her to satisfy her emotional needs. No longer as just a friend and confidant but as a romantic partner. I only snapped out of my daze and the allure of those gorgeous, memorizing, attentive eyes as we realized that our glasses were empty. We were already another three drinks in and have been talking for the past hour or two, not realizing how packed and noisy the bar had become. She grabbed my arm and guided me to the elevator, it was time to leave. I could tell she was having fun and I was happy to be along for the ride.

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It was just past 11pm when we stumbled back to the hotel, giggling. I was tipsy and she was halfway drunk. Neither one of us wanted the night to end so we went up to her room. We sat on her bed and I scrolled through the TV channels to find something to watch. 50 First Dates came up and her head perked up. It was an old chick-flick that we could enjoy while winding down the night. We didn’t say anything, we just got under the sheets with our clothes on and laid back. I’d seen the movie before but pretended I hadn’t. I laughed at the funny parts and gasped at the dramatic ones. I was nervous. For the first time I honestly believed that she liked me back the same way I’d been dreaming about the past couple of months. Was I crazy? Did I read too much into the signs? What even were the signs that supposedly existed? I had no idea what I was doing so I just enjoyed the movie while basking in her presence.

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The movie ended at 1am. She had been quiet the whole time, likely also unsure about what to make of the situation. My head was spinning, from all the day-dream scenarios and also from the oncoming hangover. I didn’t want to leave but also wanted to be respectful. What to do? My heart was racing and I was still hesitating when I heard Kelsey say, “I’m going to bed”. Without a second thought she stripped off her shirt and jeans while under the covers and nestled herself deeper into her pillows. She looked at me and said, “you joining me?”

Source: reddit.com/r/gonewildstories/comments/9uhh3f/mf_my_once_in_a_lifetime_whatif_opportunity_with