My (26F) former boss (28M) asked me out on a date… Due to his messy dating history I’m unsure if I should accept.

I was Julian’s personal assistant for 3 years, until 3 months ago. Our work relationship was fine. He was a bit of an ass the first few months, but we learnt to get along.

During my time working for him I got a front row seat into his love life and it was… messy. He went through girlfriends like he was trying to beat the world record of the most girlfriends ever had in a lifetime. I think the longest relationship he had in the 3 years I worked for him was four months and he was in another country for at least two of those months. Most of his breakups also ended up being messy too. I don’t blame the girls because he would get me to send them a gift and a note which essentially said, “it’s not you, it’s me…”. He’d then ghost them unless they showed up to his office to make a scene (most of them did).

We stayed in contact after I quit, mostly so I could help his new assistant get settled into the job. The conversation eventually turned more friendly and less business, so 3 months later and we still talk. Yesterday, he asked me if I’d ever considered going on a date with him. I thought he was joking so I sarcastically replied “yeah, all of the time”. Well, he wasn’t joking, and he thinks us going on a date is a great idea. I pointed out how messy his dating life is, and he’s claimed he’s changed and isn’t looking to mess around anymore. Obviously, people can change, but I’m not sure how much he could’ve in only 3 months.

I’m friends with his cousin so I mentioned it to her, and she thinks I should give him a chance.

Can someone realistically change in such a short amount of time? Or is he just feeding me what he thinks I want to hear? Shall I give him a chance?

TL;DR – My former boss had a VERY messy dating life, mostly because he would have a different girlfriend every few weeks and wasn’t very nice during breakups. He asked me out on a date and I’m not sure if this is a good idea.

Submitted September 23, 2020 at 11:14AM by ThrowRA_date https://ift.tt/3coCZlf