Am I going on a date with my manager?

[Kyrx94]

I’m a team leader and one of my friends who also is one is friends with an operations manager who was my manager for a couple of weeks. Once I was moved from under him she introduced us more informally on a call and since then we have all been quite close and have a group chat in place, talk most days etc.

Myself and him throw a bit of playful banter around which could possibly be seen as flirty. However it is both our personality.

His asked me today what my Bank hol plans are I just casually said nothing not thinking into it and he said does that mean we need to make some, I said I was up for it and his response was if you’re up for it want to do something?

i’m not sure how to take this. I was going to suggest bringing asking our mutual friend but not sure if he means just us?

I’ve not been on the dating scene in over 5 years so I’m not sure as stupid as I may sound right now..

We’re both very single, we spend a lot of time speaking especially over the last week we’ve on the phone for hours and constant messages. He has mentioned to the mutual friend he has been texting someone he fancies, then referenced to our texts without saying my name. We’re meeting up tomorrow, I did suggest to him inviting the mutual friend however he said he would want it to be just us. His planned the day and where we are going so just going to see how it goes tomorrow. As I do like the person he is but may be different meeting him in the flesh as we all work from home. He has some insecurities about himself and has mentioned his always scared to make the first move or be direct sometimes due to rejection in the past and how he perceives himself and this is something our mutual friend is also aware of as he has had struggles with his mental health.