I haven't followed since the beginning, but I read his "crush", and assumed it was just some girl he likes, not that they have a relationship. Women want men who can be their rock, not some wimp who will run out and buy them stuff every time they shed a tear for whatever reason, especially when they don't have any type of relationship.
As far as the whole secure part, what you said is true, but buying some corny gift or doing something cheesy for a woman when she's going through a hard time in her life doesn't make her feel "secure", it makes her feel stupid.
If you want to give her the best gift she can have right now, just sit there and fucking listen to her for an hour or two and let her pour her heart out to you without trying to finger her or whatever, and don't offer criticism or advice, just listen and throw in an occasional "Hmm" or "I see".
That's all you need. Keep your money in your wallet, women don't care about gifts for the most part.