Feeling nervous about a work lunch

[Bella1905]

I have a work lunch next week with my boss. A belated Christmas thing which was kind of him to suggest but I'm feeling nervous and awkward about it and what to chat about for 90 minutes. We get on and he's lovely and friendly but we usually just chat for a few minutes here and there, I am worried about awkward silences or waffling on about nonsense etc given it will be a longer duration. Not sure why I'm dreading it so much but I am, although I don't want to be rude and make an excuse. Does anyone have any advice? Thank you.

Is it just the two of you? Are you the only 2 in the organisation?

It’ll be fine! I’m sure they’ll be work stuff you can discuss. Also the restaurant / food itself provides a bit of conversation too. Remember, your boss is just a normal person, he’s not a different breed just because he’s your boss.

I see why you could be a bit nervous, but it will be fine. What's the deal, are you of a similar age, how long have you both worked there, big or small organisation, is there much overlap in day to day work, etc? I'm sure you will find some common ground to chat about?

Thanks both of you. No a big organisation but I am his assistant so I think it's a sort of thank you lunch. I feel silly being nervous about it but I will try and have some back up topics to discuss 😂

He is slightly older. Have worked together a couple of years but both been in the company a long time. Both have families so I guess we could discuss them.

It’s not a date! It’s not your job to make the conversation scintillating. Just respond to whatever lines of conversation he starts, and enjoy your lunch.

Thanks @HeronWing. Don't laugh but I think I'd find a date easier (if I was single and dating the right person)...I could have a drink and relax more and be more jokey/flirty. But you are right. Will try to relax about it.

It will be fine, you'll find stuff to talk about.

That's nice he's taking you out, I'm an assistant too, and have had way too many managers that wouldn't even think of sitting down for a coffee with me, let alone a meal. Thankfully I have a good one now!

I had similar before Christmas with my company directors who knew each other for years and me who had only started working for the company during the year.

It was fine. We chatted about general things. I had read some of the current news stories that morning so had that prepared to chat about.

I basically use chat gpt for anything related to small talk now. If I have to craft an email I'll just feed it some context and let it do it for me then edit. Similarly it would be helpful for a situation like this - some context and give me some topics I can talk about and how to handle awkward silences etc. It's like having a personal assistant in my pocket.

How did you get on?