I fell for my boss during my internship

This past winter, I started an important internship. It went smoothly for a week and then everything changed. I started bonding with my manager and couldn't help but fall for him. Fast forward a few months and my feelings for him grew. I suspected he had feelings for me, too. He'd shake my hand or come to my office to ask if I was OK. He'd sit down to talk with me about my master's degree, and at one point, he brought me books that he thought might be helpful.

On what was supposed to be my last day, my supervisor told me that the manager wanted me to stay longer to fill in for an employee on leave. Of course I accepted. When that employee returned, I had to go, and my manager told me he was very disappointed because he'd hoped to keep me for the longest period possible. After I left, I wrote him a thank you email, and he wound up asking me to come back to fill in for another empty position.

When I returned for more work, he changed his lunch break time to match mine, and would call asking for silly things, which made it very obvious that he just wanted to start a conversation. On my last day in that role, he said he wanted me to stay but I knew it was time to move on.

When we said goodbye, he just stared at me, smiling sadly and speaking in a very low and gentle tone. He didn't break eye contact and kept saying that I was a great person and that they'd miss me. My friends who were there told me it's obvious he likes me, but that he was probably scared because of our work relationship, and because he's older than me.

I’ve spent so much time and energy thinking about him. I never cried when I broke up with my ex-boyfriends, but leaving him felt like I was being stabbed in the heart. I don't know what I can do to be at peace with these feelings. I'd appreciate some help.

– Missing Him


Well, you don't work there anymore, so that's good. There was no way to pursue any of your questions or feelings in the middle of that internship.

Now, though, you could ask this man to have lunch – as friends. Off-the-clock social time might give you some answers about where this could go, and whether your in-office connection can lead to more.

Please remember, though, that your feelings might change as soon as you interact with him in a new space. He was great as a mentor, but in the real world, can he be a friend? A peer? Or does it still feel like he's your manager?

In a romantic relationship, you'd need more than a manager. There'd have to be some equality, which might be difficult to pull off after getting to know him in the workplace.

Start with the request for lunch and see where it goes from there. Do not call it a date; it's a platonic outing that might reveal more.

– Meredith

Readers? Should she reach out?