u/Automatic-Parsley297

My boss (male in his 40ties, office environment, UK) used to send occasionally out of common messages such as

'didnt I tell you that you're special?',

'send me the sexy <work item>'

or situational jokes such as

'we are not in a threesome' etc

This was long.time ago and it got quite calm since. Also we haven't seen each other for a while.

We met recently in his office. When we were leaving from a team lunch alone, he grabbed my hand to see my engagement ring without any heads-up, which I found a bit awkward. He also asked 'when did it happen why didn't you tell me?'. He tends to be socially awkward so not trying to read too much into it.

He also invited me for a drink after office. The rest of the team was gone at this point. We went alone and the conversation was mostly personal but not too private, quite normal, I would say.

I messaged him on my way back home to thank for the drink, as he paid, and said :'it was good to see you' to which he responded 'gonna have to find a way to see eachother more'. Didn't think much of it as it sounded like a friendly reply. He also checked on me few hours later if I made it home okay. however, 2 days later, he announced him coming to my office in the very close future and offering lunch. He seems to have a reason to be coming here, however, he hasn't been here for at least a year so the timing feels weird.

Is he flirty or am I overthinking?

My boss (male in his 40ties, office environment, UK) used to send occasionally out of common messages such as

'didnt I tell you that you're special?',

'send me the sexy <work item>'

or situational jokes such as

'we are not in a threesome' etc

This was long.time ago and it got quite calm since. Also we haven't seen each other for a while.

We met recently in his office. When we were leaving from a team lunch alone, he grabbed my hand to see my engagement ring without any heads-up, which I found a bit awkward. He also asked 'when did it happen why didn't you tell me?'. He tends to be socially awkward so not trying to read too much into it.

He also invited me for a drink after office. The rest of the team was gone at this point. We went alone and the conversation was mostly personal but not too private, quite normal, I would say.

I messaged him on my way back home to thank for the drink, as he paid, and said :'it was good to see you' to which he responded 'gonna have to find a way to see eachother more'. Didn't think much of it as it sounded like a friendly reply. He also checked on me few hours later if I made it home okay. however, 2 days later, he announced him coming to my office in the very close future and offering lunch. He seems to have a reason to be coming here, however, he hasn't been here for at least a year so the timing feels weird.

Is he flirty or am I overthinking?

My boss (male in his 40ties, office environment, UK) used to send occasionally out of common messages such as

'didnt I tell you that you're special?',

'send me the sexy <work item>'

or situational jokes such as

'we are not in a threesome' etc

This was long.time ago and it got quite calm since. Also we haven't seen each other for a while.

We met recently in his office. When we were leaving from a team lunch alone, he grabbed my hand to see my engagement ring without any heads-up, which I found a bit awkward. He also asked 'when did it happen why didn't you tell me?'. He tends to be socially awkward so not trying to read too much into it.

He also invited me for a drink after office. The rest of the team was gone at this point. We went alone and the conversation was mostly personal but not too private, quite normal, I would say.

I messaged him on my way back home to thank for the drink, as he paid, and said :'it was good to see you' to which he responded 'gonna have to find a way to see eachother more'. Didn't think much of it as it sounded like a friendly reply. He also checked on me few hours later if I made it home okay. however, 2 days later, he announced him coming to my office in the very close future and offering lunch. He seems to have a reason to be coming here, however, he hasn't been here for at least a year so the timing feels weird.

Is he flirty or am I overthinking?