To quote Mr. Spock, "I too agree, you should rethink your strategy."
The whole idea reminds me of the scene in The Vow when Tatum's character puts this whole studio together for McAdams' character's sculpting in attempt to do the same thing: get her back into what she used to love doing...and it ended up backfiring because she felt pressured and forced into it.
I like the idea of asking about painting yourself. Not only will you show interest (please only do this if you really do have interest...don't fake it) but it will give her a reason to get back in front of a canvas for more of a reason then because she feels obligated. Making someone feel obligated to do something for you is perhaps the one of the most unromantic things ever.