A work crush has resurfaced

Four years ago, I developed a crush on a coworker, "Cal." Cal and I were in the same department and started a friendship. Our coworkers were all around the same age, so we would all go out every once in a while. We were all really close – but I always felt a lot closer to Cal. Two years into the friendship, we were out drinking and I ended up spending the night with him. When we woke up, we cuddled and talked, and everything seemed fine. At work that Monday, Cal avoided conversation altogether and wouldn't talk to me. A month went by and I finally confronted him about what happened. He said he didn't really remember but said it couldn't happen again because we worked together. I was hurt and confused by this, and honestly, I was angry.

That was May 2017. That fall, I was offered a promotion, which meant leaving the department. I still valued my friendship with Cal. The group took me out for drinks to celebrate, and I ended up confiding in Cal that I was nervous about leaving the department. In the middle of talking, he kissed me. I was so surprised by this, but then we kissed again. I ended up spending the night with Cal, and in the morning we both seemed to be fine with things.

We haven't spoken about either time since, but after the second incident I started seeing a therapist about my anxiety regarding work and self-worth. Cal and work were the main focus, but over the past two years I've worked out other underlying issues. In the meantime, I've gone on multiple dates that never went anywhere, and had one semi-serious relationship. Cal and I still maintain a friendship, but we don't talk as often. Today I had a meeting with him so he could help me with a project. We worked for about a half an hour and then spent the rest of the time catching up and laughing. I started to have feelings again. At the same time, I got what I thought was a text, but when I checked it, it was a Match notification saying, "You crossed paths with Cal."

The app said we've crossed paths seven times and that was the first time I've ever gotten that notification. I see him pretty much every day at the gym during lunch and not once has it come up. Why did it come up at that moment? I was so dumbstruck I didn't know what to say or think about it. Does this mean I'm finally in a good place where he and I could possibly develop a relationship? What should I do? Honestly, I'm willing to listen to any advice at this point.

– Crossing Paths


I can't explain the Match notification. Perhaps Cal is new to the app/only recently opted in for the "you've crossed paths with another user" feature. Maybe you had the meeting in a different area of the building and it registered as a new location. Who knows?

What's clear is that you hope the alert from Match is some sort of sign about your relationship with Cal. You want to see him outside of work and figure out if there's any romantic potential. That makes sense.

Instead of looking for some deeper meaning in a push notification, ask for what you want and see if he'd like to go out. Let him know it was fun to catch up and that you'd love to grab some food. If he accepts the offer – without inviting the entire former department to the outing – enjoy the company and be straightforward about what you want next.

Do consider your new role at the office. With this promotion, would it be OK to date Cal? If so, that's great. Just make sure he understands why you're asking for his company, at least on a second outing. If you're transparent about your intentions, you might get better answers.

– Meredith

Readers? Will something develop with Cal this time around?