Socially awkward poor people, what type of events would you suggest if your boss wants to meet? I work remotely, my boss suddenly decided to tell me she plans on visiting the city I’m in (not for me) but thinks it’s a great time for us to meet IRL. She suggested a show and dinner. I live in a HCOL area, am not $ affluent, and am shy, which means a show is mostly out of my budget. I wasn’t expecting this either, and blanked out when she said this. Now I’m dreading the next time she brings it up

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Your boss will probably expense it. You can also suggest something during the day like coffee or lunch. If a show was suggested it’s likely so you two would have something to talk about at dinner. Usually managers carry the conversation so if you decided to meet in person she would more than likely ask questions and drive the conversation. If you’re worried about having to pay you can say something like “I’d love to meet IRL but a show and dinner is out of my budget can we do coffee or lunch instead?” She will will likely reply with something like don’t worry about it I’ll cover it. If you prefer not meeting later you can say I can’t do later in the day but I’m happy to meet for lunch or coffee.

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Tell her you’re busy at night but you’d love to get coffee. Be yourself and nothing else matters. I’m socially awkward too. Lol. Have you looked up social anxiety? They might have great tips. Just imagine how good you’ll feel after. Maybe write down a few things to focus on so that you don’t ruminate afterwards. Like “don’t say these five things, think before you speak, smile, have fun… you get it :)

The coffee idea is good. I’ve never looked up social anxiety before but I’ll do that. Thanks!

You don’t have to do it. But spending time with your manager (in-person) will be appreciated and can help with the relationship. This is your chance to be you outside of work. It’s ok if you’re socially awkward. In fact, it might even help your manager get to know you and understand your personality type.

Honestly, I wouldn’t sweat it! Will it just be the two of you?

Also they’ll most likely cover the cost of everything.

Yeah, so far just us, though she also invited the Head of Sales to come along, who didn’t respond. I don’t mind meeting her in person but I didn’t expect her to suddenly drop that idea. I prefer to plan ahead, not just to know the area but what to expect socially

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