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Honestly I don't know. One thing I did notice though, things seems to die when you don't see each other for a while. So your idea is probably the best thing you can do. You could still game her online, but make it more sexual, try to get her to send a sexy pic etc. Build up sexual tension before you meet, make her anticipate your encounter, make her invest something (pic exchange is a great start).
Well I did write that I would give her a kiss (did not specify what kind) the next time we meet - and I did it in a very random but funny way. She reacted with lots of "HAHAHAHA why?" kinds of answers, but slinked in an "okaaay xD" somewhere in the middle. She's very shy in real life, but didn't say no, so I take that as a good response!
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I suck at this stuff, but I personally have decades of experience with your exact question.
No. Don't do it. Period.
Making a woman feel sorry for you will not get you laid or get you a girlfriend. You will buy a one way ticket to the friends zone at mach speeds.
I know because I did the exact same thing you are suggesting. I also have had depression for over a decade.
Attract her the normal way, and not by making her feel sorry for your weaknesses.
You're right. Though I know it's possible, since I have a friend who's insanely good with women, it's a risky road.
And the depression is disappearing now anyways. I've made plans with my best buddies and good looking girls, and I'm getting somewhere with my band - having a great life sure is essential for good inner game!