How do you become “real” friends?

I work in a place with a lot of guys who are 1-3 years younger than me. They’re mostly friends outside of work, or at least know each other and occasionally frequent the same parties. Every day it seems like they’re talking about something that happened outside of work. When we’re all there, working and hanging out, it’s really a lot of fun. Never fully seems like work to me because I enjoy the atmosphere so much.

But tonight, I was invited to hang out with them… outside of work. First time! It sounds really lame but I definitely want to go. Is that weird? Are they THAT much younger than me? (23 vs. 19-21). It will definitely be hard to go from work friend to friend friend, but I really do want to. I decided not to go tonight, but the question still stands. How do I make the jump without it being awkward, if they ask again?

Oh yeah, one last piece of info… I’m their boss.

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8 thoughts on “How do you become “real” friends?

  1. theattack says:

    [That last piece of info is a pretty big piece to leave out. It changes this situation from “how do I be friends with them” to “should I be friends with them?” If these guys are the only other people at your workplace, becoming friends with them should be fine. But if there are other employees around that you would be excluding or could misconstrue your friendship with them as favoritism, you should keep your relationships professional but friendly.

    Assuming that it’s okay for you to be friends with them (though I’m not so sure that it is), you’ve really damaged the chance by turning them down. You’ll need to ask them when their next outing is and when you can join them again, so that they know you’re still interested.

  2. DavidIsGreat says:

    [Don’t do it. The age thing wouldn’t matter, in fact it gets less important as you get older. But the boss thing is a potential problem. It creates situations where you’re putting your own job in jeopardy. I can elaborate if you want but I have the feeling that you probably know what I mean.

    Being the boss sucks. it’s lonely at the top, but you’ve got to worry about your best interests. You can be friendly, share interests, talk about a lot of common things. But as long as there is a subordinate relationship you shouldn’t try to hang out or even be that close.

    But without the boss thing, three years? Who cares, go see the Dark Knight or whatever, that’s nothing

  3. Happy Pants says:

    [Yeah, the age thing isn’t a big difference. That shouldn’t stop you from hanging out with them outside of work. But the fact that you’re their boss could make things awkward, and might keep them from being “real” friends anyway. They may be smart enough to watch everything they say around you and be careful of how they act, in which case you still wouldn’t feel like part of the group. And if they don’t, you’d have to remember that you’re their superior, and you’d have to act that way as soon as you got back to work.

    I’ve known boss/employee friendships that have worked, but it’s a very tricky situation. At my old job, I knew that if my boss and I had met under other circumstances, we would have been friends, but since we had that dynamic to worry about—and that dynamic was pretty strained as it was—it was better to wait until after I quit to hang out as friends (which we did, and it was great).

    The thing is, I do think you can hang out with them outside of work. You just have to be really careful about it, and don’t drink in front of them unless you’re the type of person who can have one casual beer, without getting tipsy, and then walk away. You can be both friendly and their boss; it’s just a hard balancing act to do.

  4. Brandon Sklar says:

    [I would like to talk specifically about the comment you made about the uneasiness you felt about the age difference.

    I have noticed that when we all tell other people our age and we are immediately placed in a category in a lot of peoples’ minds. For instance, I had a friend, nervously, go on a date with a cute co-worker a few months ago. According to him, things were starting out really well, and then they finally got around to the subject of how old they were. The girl said that she was 23 and my friend hesitantly admitted he was 19. After that she immediately placed him under a friend column and shut off all romantic interest. Although things seemed to be going great, once age was brought on to the table, none of that really mattered. So what IS age, exactly?

    Age, to me, is just an arbitrary number. It is how many days we have happened to survive from the moment of our birth. To this very moment I am typing this, I have been on this earth for 7,482.5 days, which equates to 179,580 hours, oh, correction, 179,582 hours (since I was born at 5 P.M). And that is 10,774,920 minutes. Yes. I have been alive for over 10 and a half million minutes. You impressed? I know. I have tried really hard to get to this point. I had to survive two bouts of pneumonia, three cases of teenage heart break, and consuming enough soda to fill an Olympic-sized swimming pool. Kudos to me!

    All of these are just numbers– numbers which really have a significantly lower impact on who me and you are than society tells us. I get really frustrated when people tell me something like: “I think I could really only date a guy who is, like, 2-4 years older than me TOPS.” Or “How could I be friends with her? She is like… 6 years younger than me!”. Maturity and age may have a positive correlation, but age certainly does not cause maturity… experience does. And some 18 year olds experience more than some 40 year olds. I am great friends with someone who is 7 years older than me and 4 years younger than me.

    Perhaps a better way at looking at it is not what age we really are, but what age we are perceived to be through our actions. For instance, another friend of mine is 20, and she went on a date with a guy she met at work. He thought that she was roughly 26 and she thought he was around that age as well… Turns out he was 32…. Yikes, right? But they have been dating for half a year now and things are going fantastic for them (other than the unjust, outside scrutiny they have to deal with). Although you are not specifically talking about romantic relationships, I think friendships can apply here just as well. The whole befriending your underlings thing I am not qualified in really giving sound advice on… But their age should definitely not play a factor in your situation.

  5. Missy says:

    [I think it’s cool that you want to have a friendship with your supervisees, given you take the advice outlined above about knowing the boundaries. It is tricky, though. I was “friends” with one of my supervisors outside of work until she started getting really passive-aggressive in her roll as my boss.

    As long as you can wear two different hats with these guys, you should be fine. Just don’t wear them at the same time – it gets too entangled. And it looks funny.

  6. lilredbmw says:

    [Well, I am glad you eventually added that very important part about being the boss! While the age difference is hardly a difference, the fact that you are their superior can change things. I think it is entirely possible to maintain a social and professional relationship with these people, just go about it in an intelligent and thoughtful way. In fact, some of my closest friends are co-workers. For example, if there is a birthday party for a co-worker at someone’s house or a restaurant, by all means go. If you drink, do so responsibly. However, if they are all going to a strip club, go ahead and deny that one. And when you are being social, be social. Don’t bring up work-related things, because it draws attention to the fact that you are the boss and that’s when it can get awkward. I agree with Dennis that being friends with co-workers can boost morale, build a strong team, and create trust. But, since you are the boss, just be a little bit more careful.

  7. AKchic says:

    [I think we need to know the industry you work in and the setting you wish to “hang out” in. This makes a world of difference.

    Example: I work in the substance rehab industry and I’m one of the younger folks. Sort of. I’m under 30. But, I work in admin and the other non-college admins are younger than me. We’re talking barely 21. I’m nearly 30. There is a generation gap. The “professional” folks in admin are in their late 40s to 70s (the ED here is in her 70s). Very few are in their 30s except for some of the counselors.

    I am friends with some of the people here at work. Some from other work settings (I used to work with some of these people at other places – the jail specifically, or at the DoD), some are friends I’ve picked up here.

    An occasional lunch with the Admins, sure. Lunch with my bosses, maybe (it’s happened before). Dinner with the bosses, yeah, it’s happened. No, we don’t drink because it’s unprofessional. When my friends and I go out, we don’t drink. Why? If something were to happen in public, the repercussions would be dire.

    As a boss, you set the example. Even off the clock. What happens if you need to fire one of these guys? You think they’ll see the difference between “friend Joe” and “boss Joe”? No, they’ll just see “Joe” firing them. Plain and simple. Keep your lines clear.

  8. Love and Ink says:

    [I agree with AKchic.. it would depend on where you guys are hanging out and what the agenda is for the night. If it’s something like drinking, dancing, and hanging out in one of their apartments – then I would say don’t do it. They won’t see you the same after that.

    If it is something like a lunch or dinner, somewhere conservative that’s quiet to chat then I think it’s okay. It seems a little more professional and less inappropriate that way.

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