Boss Vs. Boyfriend

Monday | March 13, 2017

Love Letters Dating

Boss Vs. Boyfriend

Hi Meredith,

I think I am falling for my boss. The work is remote. We live in different countries, thousands of miles away. We talk almost every day via messaging app. Most of the conversations revolve around work; there’s no flirting, and I am 100 percent sure he really has no other feelings for me than liking me as a great employee/business partner. I report to him directly, and he discusses most decisions with me.

Everything has been great, but all of a sudden I can’t get him out of my head. We are close in age, and he’s charming, smart, inspiring, and exciting. There are definitely more than enough reasons to like him. The tough part is that I am engaged and living with my boyfriend who I’ve been with since I was in my late teens (we’ve been together for six years). He is my first love and has been with me through hell and back, and he knows me even better than I know myself. I love him completely, and our relationship is good. Of course there are things that annoy me, and I’d say that he and my boss are polar opposites. My boyfriend works, but I’m the one who actually earns the income. This might be one of the reasons I have started to feel this way. With my boyfriend, even though he is brilliant in his own way, I do not agree with many of his plans, he’s very stubborn, sometimes even rude, and I don’t have confidence in his decisions. Also, I am having second thoughts about the future. He would like to move to the country and live a very quiet life, but I’m not sure if that’s what I want. I would like to travel the world a bit.

Neither of them have any clue about my thoughts, and I don’t want them to know. I love my boyfriend and I don’t want to hurt him with these silly fantasies. Then again, I would like the other guy to hint that I’m not just a co-worker for him. Am I complete fool to fall for someone who is SO out of reach? Should I just snap out of it and try to just go with the life plans my partner has for us? Or should I just wait, do nothing, and just hope these feelings will pass?

– Second thoughts

You list three courses of action at the end of your letter, but let me add a fourth. You have the option of ending your relationship to see what else is out there. You can break up with your longtime partner without knowing what’s next. It’s time to admit that you and your boyfriend are no longer on the same path, and that even though you love him, your fantasies take you elsewhere.

For the record, you don’t really know your boss – not outside of work and the messaging app – which means he represents something bigger, maybe all of the things you’d want from your next relationship. Think of him a symbol of possibility. It’s not one man vs. the other.

If you remove all sentences about your boss from this letter, you’re left with a paragraph about a relationship that made sense when you were young, but no longer works, now that you’re a 20-something. It’d be great if you could just stumble into a new relationship with a perfect, ambitious person on the other side of the world, but that’s not how it works. You might have to leave this relationship and be on your own for a while. It’ll be scary, but good decisions often are.

– Meredith

Readers? Any other options?

Dating Office