I attended an event with my client company last week (I freelance) and got to meet lots of the team, all great.
I offered to pick people up who were nearby but only one said yes so off I go on the day and pick up one guy, P. First time meeting.
P is perfectly pleasant if slightly awkward and we get to the venue, where he hands over a bottle of real champagne and a card as a thank you gift. Extremely kind and I tell him so and thank him very much.
We go to the event where he insists on buying me a very expensive cocktail (I was getting one but he insists on paying). Keeps offering me wine despite me declining as I'm driving. At 10pm we are about to leave and he turns up with another cocktail that he says he bought for me, I say absolutely not, he then says he actually bought it for himself but that I should 'have a sip' 'oh go on' etc. I decline but have to do so quite strongly. By this time he's had well over a bottle of wine to himself plus to two cocktails over about 4 hours.
We drive back to my car with someone else and he's over sharing, keeps taking about being devorced, keeps asking about me (I tell him I'm married a couple of times) but it's fine, he's a bit tipsy so whatever.
It's now 1am, I drop him and the other guy back home and go home to bed myself all good I think, great day, nice people.
I get up this morning and fetch his gifts from the car to show DH, open the card which says thank you very much, and £40 falls out.
I think if it wasn't for the cash, I wouldn't think twice but now all the other things are bothering me a bit and I'm slightly uncomfortable with it all. I want to brush it off as him being just a bit clumsy and trying to be nice and going a bit overboard.
The thing is, with the cash I really feel like I should send him a message thanking him again but I don't really want to engage.
I'm possibly overreacting here, I had a work colleague befriend me in a similar way in my 20s and it became very clear he wanted more to the point of inappropriate behaviour and so this latest thing is setting off my instincts.
So what does everyone think? Leave it? I'm unlikely to see him much and I'm not really in a position to complain as I don't work for the company. He hasn't really done anything 'wrong' either.