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There are people at my local brewery I enjoy chatting with casually during down time. We've had some good conversation and things have gone great.

My problem is how do I go about inviting them to hang out outside of their workplace? At what point/time in the relationship do things reach the "next level"?

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Tell them about an event that you will already be attending and which you do not control, such as a local trivia night or a concert in the park, with no implied obligation.

Social stuff with service staff is weird because they have to be friendly with you or they risk losing their job. Your instincts may be good that they genuinely like you, but you don't want to put them in the place of feeling pressured into something outside of work.

The next time you plan on going to some public event that you think they'd like, mention that you're going and that they might find it fun. That way they can give a solid "yes," a genuine or polite "maybe," or can say "no" in a polite way without worrying that you'd feel let-down.

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Well, first off, you need to ask yourself whether they want to be closer friends than they currently are.

Service staff are likely to generally see you as customers. Sure, exceptions happen, but don't assume.

That said, I have made loads of friends who work in bars, restaurants and clubs, and key to it is being friendly and personable. Listen to them, be interested, chat about things, find common interests. Pretty much the same as making friends anywhere, but with the added wall of a service relationship to get past first.

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One way is to make a "no pressure" invitation.

Since you have talked a lot, you should know what your common interests are. Let's say, for example, you both like dogs, and you both have dogs. You can simply invite that person to meet up to walk the dogs or to meet at a dog friendly park. You can simply say that you will be there at a specific date and time. Then leave it at that. So the intent is to let the person know where you will be, when, and what will be happening there. Le them decide whether to go or not without having to say a word about it.

If the person shows up, all to the good. If the person does not, just let it go. Sometimes you just have to wait and see. But since they know that a polite invitation was made, when they are ready, they may invite you to something.

Only time and circumstance will tell.

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