\*\*TL;DR:\*\* We were on a company-wide teambuilding/vacation for three days and I really liked a coworker’s personality, jokes, her story… I want to get to know her better but I’ve no idea where to start since she works in a separate department and we don’t work together. I do have a slight crush on her but I’m completely fine being just friends – I like being surrounded by fun people and she seems like one.

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So yeah – it was a 3-day vacation sponsored by a company, a getaway out to sea-side in a resort. It was 150-ish people but I mostly hung out with my group of 10-20 friends. Some of them I’m really close with, some of them I barely know, but we almost always go out for a break together.

In any case, a coworker joined us on several occasions who I’ve never met. She joined the company half a year ago but I worked remotely so haven’t had a chance to meet her in person. She sat next to me by chance and as soon as we met and started talking we immediately clicked. It was super fun. I’m fairly energetic person, I love the sun, sports, love hanging out, playing cards on beach and she’s EXACTLY the same. For three days any activity that our group did (again – cards, volleyball, coffee, beers, anything), she was there and was hyped every second of it as I was. What I also like is that she seemed extremely self-confident, and didn’t have anything against making jokes on her account. I also joke a lot on my own account, so we constantly picked on each other.

All in all I was really surprised and I can’t remember last time I had this much fun with someone. I’m not sure if she had as much fun as I did, but since she was often joining our group I’d think so.

In any case I’d really like to get to know her better. If we didn’t work in the same company I’d immediately ask her out, but obviously in my case I don’t want to be creepy. I need to make a stop here and say that I completely understand relationships at work can be difficult and can mess things up. I also understand that hitting on coworkers is a no-no, obviously unless the feelings are mutual. What I’d like to get out of all this is to have one more person I can hang out with and see where things go.

10 comments
  1. I don’t think you need to overthink this.

    “Hey, I really enjoyed meeting you. Here’s my email/phone number. Drop me a line if you’d ever like to spend some time together outside work hours.”

  2. your company sounds big enough that if you take your shot and ask her out, you can still avoid her from the day-to-day basis so that you don’t need to feel weird every day.

    you want her as a friend but you’d rather have her as a girlfriend, so go with that route.

  3. > I do have a slight crush on her but I’m completely fine being just friends

    Better to ask her out now and get shot down and settle for friends, than be her best work buddy then make things awkward by asking her out in 6 months.

  4. I think it is fine to simply ask someone from a different department out. It is better to make your intentions clear. I would probably add her on Facebook first or see if I could verify that she does not have a partner before tho.

    If you really like her imo it is worth taking the obvious risks of asking out someone from the same company. I would find it annoying if someone spent time befriending me while it is clear from the start they want a romantic partner.

  5. What is the company policy on these things?
    Play things out, let’s say you really both dig each other and start dating, company finds out, fires one or both. Could the relationship withstand this? Would there be resentment? If there is a policy, would you be the one willing to walk away from the job in order to have the relationship?
    Adults suck at meeting people and making friends, and friendships and love spring up in work places a lot. There is nothing wrong with that, and you should pursue your own happiness. But, if you are actually in love with a person, you should think about theirs as well. How important is this job to her? If she’s been working her life to get to a position and it is your intention to compromise that career success, even if she is complicit, you’re not being a good friend. Play the long game.
    But, at the core, there is nothing wrong with making friends with coworkers and hanging out with the people you like and whose company you enjoy. There are issues with office romance, but they are waters that can be navigated.

  6. >I love the sun, sports, love hanging out, playing cards on beach and she’s EXACTLY the same. For three days any activity that our group did (again – cards, volleyball, coffee, beers, anything),

    If you have a coed volleyball group, invite her to it. Since you have shared hobbies, it’s really easy and fun to meet up outside of work.

  7. Ask her to get coffee, or do something you spoke about enjoying. You’re definitely overthinking this. You two hung out for days and had a blast, asking to hang out is not gonna be weird. Asking on a date wouldn’t be weird, but with the work boundary, I think you’re right to just see about hanging out first.

  8. Jeez, all these cloak and dagger strategies. You both are adults so just call her. Just be 100% certain she’s not married or in a solid relationship.

  9. Def invite her out . Offering her your number seldom works. Women want a man that takes charge in my experience. What’s the worst that can happen? She says no or tells you she has a bf. Ask her out to coffe or drinks.

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