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I work with three colleagues in a small open space. We're developers. We've been colleagues for almost a year and got to know each decently.

I'm a shy, socially anxious person that doesn't have many friends. I would appreciate making new ones. I get along well with most people. So far, I maintained a friendly although a bit distant image to all of my colleagues.

I would like to break the ice with one colleague in particular (say Bob), who is the only I appreciate deep down. So I would like to invite him to have a drink or eat after work, bringing each other's partner.

The problem is, Bob isn't in my team, so he's not the one I socialize the most with, and my other two colleagues might get upset they didn't get invited. So far and for all that I know, afterworks were rare and strictly collective. We're in a close space and Bob is chatty, so I guess even if I did invite Bob privately they will soon or later learn I've (tried to) befriend Bob and not them, which I find embarrassing.

How could I deal with this situation in a tactful manner?

  • Have you ever socialized with any of your colleagues outside the office before? You mention previous after-works, but it's not clear whether you attended. – ekl Sep 13 '19 at 18:41
  • @ekl I did attend, it went well – Arthur Havlicek Sep 13 '19 at 18:49
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I would skip repeating the part where you described yourself as shy etc., and jump to a bit similar situation I am/was.

I would suggest starting with low-key activities which you know Bob does.

I and one of my friends, say D used to go cycling on weekends. My friends whom I told about it (after being asked, "Where were you today?") were not surprised or jealous at all.

Another friend G, who's my senior, and I regularly have coffee as the cafe is close to where we study. It is no big deal when, while studying, after yawning, he says, "Hey! Coffee?".

Another friend lets say T, and I go and click photos in the evening, and sort/ edit them in the café. Thus we used to drink something there pretty naturally and later on, he had stopped me sometimes after classes and had asked for a coffee.

All of the above three cases have some things in common.

  • D had asked me earlier if I like cycling or not, and if any other sports. After which he casually asked about one weekend and told me to decide the destination etc. We did this 4-5 times.

  • G knew I am a daily visitor of the café and would not mind having another and gossiping with someone.

  • T and I both are interested in photography, and since coffee was an intermediate step, it was normal after which even if it was solely for talking and coffee, I didn't mind.

I would be reluctant to go somewhere special/ expensive/ out of daily routine/ somewhere that requires me dressing up.

And as you're worrying about your two friends getting annoyed for not getting invited, I would present an example I've seen my friend A doing. When we go for walks in the evening for reliving ourselves of thoughts of the day/week and rant about other people, if someone asks where we're going etc., He'd just say "On a walk around the campus, maybe eat something somewhere. Would you join?". If people do join, we cut short our walk and they don't ask us again. If no, it's all well and good as this isn't something they'd crave to join anyway.

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