Your birthday is next week? Hello, fellow Virgo and happy early birthday! 
OT: Yeah, you could give it a try. Although, I must ask, without going into detail, define "complicated". If the relationship is complicated, why would you want a kiss from her? What you have to ask yourself is: Is it worth getting a kiss from her? Or should I wait until another girl comes into my life to try the kiss thing? (Remember, at Christmas time there mistletoe. There's plenty of time to find a better mate female friend that the one you are currently talking about between now and then.)
If she says yes and you kiss and the relationship becomes stronger, do you want to be in a serious commitment to her?
I mean, if you want to ask her go ahead ... as they say, "nothing ventured, nothing gained" ... just set your hopes accordingly and look at everything that can go right or wrong.
OT: Yeah, you could give it a try. Although, I must ask, without going into detail, define "complicated". If the relationship is complicated, why would you want a kiss from her? What you have to ask yourself is: Is it worth getting a kiss from her? Or should I wait until another girl comes into my life to try the kiss thing? (Remember, at Christmas time there mistletoe. There's plenty of time to find a better mate female friend that the one you are currently talking about between now and then.)
If she says yes and you kiss and the relationship becomes stronger, do you want to be in a serious commitment to her?
I mean, if you want to ask her go ahead ... as they say, "nothing ventured, nothing gained" ... just set your hopes accordingly and look at everything that can go right or wrong.