Not sure how to pull this off

[trashKENNUT]

MattRyan,

I live in an apartment community and the property manager is this hot cougar. When I first signed the lease I tried to keep the conversation going with her but she had to get back to work. It's hard to get any interaction with her because I don't feel like coming to the office for nothing while she's trying to work. They have a Christmas party for the community every year and I went but I felt out of place because I was one of the few young people there. I ended up probably looking creepy because I just hung around all night and waited till most of the people left so I could talk to her. I ended up chickening out because I didn't really know what to do and I was also wondering if I could get kicked out or charged with sexual harassment if I stated my interest.

Feel you man,

I don't suggest going all out, because she is indeed busy and you be tryhard to talk to this girl in a working environment. Do get back to office and really get some things while engage small talks with her. Slowly build that up with when you meet her occasionally somewhere else.

Just small enough steps and subtly hint that you want her to ask you out for coffee or dinner. She's the manager right? So definitely she will see you as one of her subordinates.

Zac