I worked at a startup where I had a crush on a coworker on my team. We were both working from home so all of our interactions were on Google Meet and WhatsApp calls. We never had any face-to-face interaction, and she had never seen me. I had seen her display picture, but I didn't have one. I would rate myself as an average looking guy, but I’ve been insecure about my looks.
I was the tech guy and she talked with clients would come to me with issues. We worked together for four months, talking on WhatsApp almost daily. She was about five years younger than me, was quite confident, an extrovert, and nice to everyone. I am shy and an introvert. While all our calls were for business purposes, I used to crack jokes and she would laugh. She would occasionally confide in me about issues and conflicts that she had to deal in the job. Occasionally we would also talk about movies, TV, and comedy. Just when I had started to like her, she resigned due to some conflicts with the founder of the startup. During the notice period I would send her DMs asking how is her preparation going, giving tips on how to apply for interviews. She never asked for it, though.
Eventually she got few offers and she decided to leave before finishing notice period. Two weeks before, I had told her that I had a crush on her. It was purely impulsive and a stupid decision on my part. I don't know what I was thinking. I thought I had no chance anyway, so take the shot, I guess. She politely rejected saying she saw me as good friend at the company. She didn't tell me when it was her last day, so I called her up and she talked about her new job and how happy she was. I wanted some kind of closure, some kind of response from her, but she didn't say anything. I told her I will miss working with her. I was already vulnerable by then and sad. Maybe to console me, she said that I could message her anytime.
I was slightly irritated by this in my mind. And that was the end of our conversation. After the call it dawned upon me that maybe I had been bit too desperate in my approach. All our personal conversations were initiated by me. I was always trying hard to be funny. She would almost always reply but maybe she was being professionally polite. That day, I decided not to initiate any further conversation with her for the sake of my own ego. It has been four months since we have talked. Meanwhile, I also faced some issues in the company and resigned. I was jobless for two months. Was it too much to expect a message from her? I even put up decent profile pic on WhatsApp a few days ago. I was expecting that she would look up my LinkedIn profile once, notice that I had resigned, and ask how I was doing. I am pathetic, I know. Overthinking is killing me.
She told you she thought of you as a work friend. I'm not sure what else you need to hear.
She was so clear – which is a gift! If she had given you a big "maybe," there'd be more to overthink about.
There are some lessons here, though, so let’s go through them.
1. You knew all about her because she was an extrovert with a profile picture. It was harder for her to think about you the same way, even with some friendly small talk, because she knew so much less. If you want people to see you, let them. Keep that picture up.
2. There were moments when you could have tried for an after-work hangout, just to see if she was open. You both like movies? Great. How about, "I'm going to escape from work, eat 1,000 Junior Mints, and watch the new Marvel movie this weekend. Want to join me?" Out-of-the-office time – even when it's a home office – gives you the chance to see if there's something really there. Next time you bond with someone, ask for what you want.
3. Telling someone you have a crush on them is very cinematic. I have done it, and it feels very brave. But the other side of it is weird, because if someone says "I have a crush on you," and you've never spent real time with them, you might feel like any small outing would be high stakes. This is my case, again, for Step 2. Better to have a smaller, specific ask for social time, especially with a coworker, than to make a big proclamation that might not even be true. Maybe in person, she's not what you think. All you really knew was that you wanted a date.
4. Giving unsolicited advice to a woman – who's an extrovert and good at her job – is maybe not the best way to bond. I know you meant well by giving her tips, but better to ask questions than to tell her stuff she might already know.
5. You expected her to do a bunch of stuff after she left, but you were setting yourself up for disappointment. She's busy with a new job and you know nothing about her other responsibilities. Also, she wants to maintain boundaries. If she'd reached out the day you changed your LinkedIn page, would that have suggested she might be open to something more? Who knows?
6. Dating – and crushes – involve a lot of rejection. Be disappointed, feel sad, treat yourself to something you love, but don't be irritated, angry, or create extra problems that aren't there. She handled this with honesty, and now you can move on. Your response to this very normal experience can be picking yourself up, laughing it off, and thinking about what's next.
7. Remember that this has been good for you in a lot of ways. It was social practice – which we all need – and it made you more open to new experiences. Now is a great time to seek people who are looking to date. If you can put a picture up on WhatsApp or LinkedIn, you can do it on a dating app, right? That’s a much better use of your time than seeking out someone who has told you directly that romance is not on her agenda.
Readers? Help this LW figure out how to snap out of it.