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Risk/Return and a Cupcake. (And a co-worker.)


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I work in a 30-person office for a large company in the financial sector. Last fall, we brought in a new guy to head our bonds team. As soon as he got there, I hit it off with his assistant, Megan. (The new bond guy and I get along fine, too.) She’s a brown haired Pam Beesley. I was immediately smitten with her. After she left on her first day, one of my other colleagues loudly said, “MagnumOpus is giving the new girl the doe eyes!”

 

I do have a rather expressive face...

 

I’m a career first guy. I keep things professional. I’ve never crossed the work/play line before. I’m moving into a leadership role in a completely different division than my colleague and his assistant.

 

It became apparent quickly that I had also caught her eye. It started out as lunch, and then one Wednesday night she sent me a text at 9:30pm to ask if I was going to bed soon. I played coy and told her I didn’t know, and asked why. She asked if we could meet for a drink. She had a question for me.

 

We stayed out until 2. It was great ‘getting to know you’ talking. At around midnight I asked what her pressing question was, and she shied away from it. Never gave me a real answer. We said good night and we were both bleary eyed at work in the morning.

 

She asked if I wanted to do dinner the following Friday. We made plans. Friday morning, though, a colleague came up to me and said, “Megan just told me she heard someone say you have a thing for her.” “Oh?” I asked. “Who’d she hear that from?” “She didn’t say,” said my colleague. “Well, that’s interesting,” I said. He was useless to provide me more details about this. I kept my cards close to my chest. I neither confirmed nor denied a thing.

 

Around 2pm – I had another similar exchange with a different colleague. This doesn’t seem like a good thing, right? Right. I let it go and kept on doing my thing. If I said a word or showed a sign, I’d lose. 4 pm rolls around and Megan texts me to tell me she won’t be able to make it out tonight – we’ll have to do things another night. I have misread the situation – I decided. Time to back off. Waaay off. Cordial and professional in the hallways. No more texting after work. None of that.

 

That same weekend, I started dating a good friend of mine. We’ve flirted for years and though I’ve asked her out before, she just that weekend decided she was ready to give us a try.

 

I kept my distance from Megan and she seemed to reciprocate for a while, but then started to find her way back over to my office more and more. There’s professional grounds for us to speak maybe three times a week. Any more than that is banter – and we quickly moved back into banter. She hinted a few times that she wanted to go out again – once asking if I’d been to a restaurant nearby and saying “Maybe we’ll go there for lunch some day.” To be safe and maintain distance, I replied with, “Maybe we will.”

 

My liaison with the other lady ended suddenly and not that long after it started. She dumped me after she realized, “she’d never be able to fall in love with me.” I’m not the guy who sits at his desk and doesn’t work for a week after a rejection – but, the expressive face holds true... and as my job generally involves 70% client interaction and 30% paperwork – people notice when you suddenly find a way to start doing paperwork 80% of the time. I was bereft. What a saddening statement, and reason to be dumped.

 

On Wednesday evening, I got a text from Megan. It said, “I know this is none of my business – but you have looked incredibly sad the past few days and have hardly said a word. I won’t ask what’s wrong – because it’s none of my business – but I’m here to talk if you need someone to vent to. And I hope you’re okay.”

 

I was touched by her gesture and – without taking it as an opportunity to mope – gave her a three paragraph version of the breakup and why I was upset by it. She was supportive and sweet, asked and listened. Maybe getting breakfast this Sunday will make you feel better, she suggested.

 

Breakfast lasted four hours. We sat and talked until it was clear the server needed our table. We drank mimosas and then went for a long walk together after. She told me about her family, we discussed past relationships a bit, discussed what we want out of life. If it had been a first date, it’d have been a great one.

 

She texted me the night before Valentine’s day to ask if I better liked chocolate or red velvet. I asked if she was bringing treats to work. That morning, she told me she had something for me – but I couldn’t have it yet. A single cupcake in a small cardboard box was on my desk right as the day ended. I was half expecting a note in it. There was no note, just a very sweet guesture. I called to thank her that evening.

 

We’ve gone out twice more since then. We already have plans to see each other the next two weekends. The conversation flows so well. Our senses of humor mesh. We spend the whole time laughing. I can make her laugh until she’s got tears in her eyes. We saw a movie together last weekend (Gone – which was terrible, by the way) and while there was no arm-around-the-shoulder nonsense, we were leaning towards each other the whole movie, sitting shoulder to shoulder and whispering Mystery Science Theater style commentary back and fourth. We text all day both at work and after. We’ve been exchanging banter as I’m typing up this post.

 

I have a job I cannot give up. Megan has a job that pays the bills, though she’s disclosed that she’s been looking at other options both with other companies as well as in different divisions of ours. For a man who sells risk for a living, this is a risk I’m having a hard time analyzing. I can see having a successful, positive relationship with this woman and don’t want to lose that by playing it so cool for so long that she gets tired of the chase. Dating is not explicitly prohibited by our company, but I’m not willing to use that detail as an excuse for something that is definitly a faux pas. I want to find a safe way to say, “Hold that thought.” I’m fantasizing about saying, “I wish we weren’t co-workers,” when I see her on Saturday and then giving her a light kiss when she asks why.

 

I need some sanity. Some suggestions. Someone who doesn’t feel like a 15 year old juggling emotions and the chance at being the fabled youngest VP in company history to point me in the right direction. I don’t want to hear “DON’T DO IT FOR ANY REASON,” but know that some of you will say that, and that I should listen... but I don’t want to listen!

 

Your thoughts are greatly appreciated.

Posted

Help her find a job elsewhere.

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