love letters by meredith goldstein

She fell for her boss during her internship

Q.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.

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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 e-mail, 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.

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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

A.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 something very different than what he’s given you so far. 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.



It sounds like this guy liked you as an employee but I don’t see this going anywhere else. You made a fantasy in your head that something was there that wasn’t. Now that you don’t work with this man, feel free to ask him out, but don’t be surprised if he shoots you down.



I applaud this guy for looking in your eye and saying thank you and nothing more. I imagine you are leaving out the part about wife and children.


If you’re single and he’s single, reach out. Nothing ventured, nothing gained. You can’t win if you don’t play and all those other cliches. The worst that can happen is that he rejects you. Can you live with the what-ifs?


I think this is what grown-up business people call “mentoring.” Try to understand that despite your supreme confidence in yourself, you (and your friends) most likely misinterpreted his feelings/intentions. And if you two no longer work together and he really was interested in you he’d ask you out. He didn’t. Pretty much says it all right there. Move on. BIGSIGH

Sorry, but I don’t see anything concrete or convincing there other than that he enjoyed working with you, thought you were a great employee, and that he’d like to have kept you on due to that longer if he could. That said, if you like him, let him know. You don’t work there so you have nothing to lose, unless you are really holding out for a job there. In that case, then you have to decide which is more important. SEXUAL-CHOCOLATE

She obviously does not see him as a creepy old guy. She had boyfriends and feels stronger about this guy than them. Unless he’s married, I say she goes for it.


You need to take serious the fact that if you try to strike up a relationship with him, you are also compromising your ability to return to the company and to receive a fair professional reference. If it’s really killing you to walk away, then maybe that’s a worthwhile cost, but it’s not nothing.


This is no way to start your career in your chosen field! Dating the boss, or former boss, is career suicide. You may find yourself working for this company again, and you don’t want any messiness to get in the way. Here’s something they don’t teach in college -- if you date the boss, you’re more likely to get fired, not the boss. Unless you sue the boss, in which case you’re unlikely to get hired anywhere else.


An intern with an office? Now I’ve heard everything! URKIDDINME

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