Jack's tilde abuse is straight out of the Myspace era, and as a former teenage Livejournaller I kind of love it.
BTW I'm still mulling over the dressing like a lesbian thing. Obviously there is no official lesbian dress code, but...well, I suppose the stereotype that would come to mind is butch, and Jack doesn't dress that way? She did a bit many years ago, when she had short hair and was the most lesbian lesbian ever to have lesbianed, but those days are long gone, and the last time she showed off her famous masculine aesthetic it was with a cable knit jumper.
Unless pig skin hats and expensive pastel jumpers are particularly sapphic and I am unaware of this, I would almost suspect that Jack herself made the comment? Like, "Ooh look out Harold, I dress like a lesbian, no one will think we're together?"