Hi there, happy new year!
I have had this history with a girl for a good few years now. In a nut shell she had a boyfriend who worked away we became inseparable, I fell for her in a big way told her (when they were on a break) she reciprocated the feelings but nothing happened because she went back with the boyfriend. We cut contact for 2 years, I stupidly got back in contact in July, turns out they had broken up a bout a month before. We have gone down the same road again by slowly taking more, spending more time together, and I know where this is leading again.
Over the last few weeks the word 'date has been used by both of us, one example is the other night when I was playing poker she text me saying 'if you win at poker are you going to take me out on a date?' I then asked her to go out the next night, she was busy but said we could do it another night. This was a few days ago but nothing happened yet.
I want to know if people use the word date to friends because to me you wouldn't do that, especially to someone you know has had and has feelings for you?
She bought me christmas presents and the words all my love is used in cards etc, she text me new years eve saying 'Happy New Year you absolute gem, love you loads xxxx'
She is going away for 4 months in two weeks and I know I need to tell her how I feel (again) and I either want to make a go of it or the friendship can't carry on how it is, not for my own sake. Struggling to see how to tell someone I love them for a second time and possibly get rejected again.
I know I do a lot to help her out and sometimes do think she plays on that but also know she genuinely cares for me and has had feelings for me in the past, we have always had a very strong connection.

So back to the question of is she just playing around asking for us to go out on dates or do you think she means it?
Thanks in advance for your help.