"If a guy, who's a friend but you've sorta got a thing with him (after that one time you made out), has told a mutual friend in your presence he's single because he's 'too busy with two jobs to give the proper attention to a girlfriend right now,' but keeps in contact and then doesn't and then does...what is a girl to do? What is going through this guy's mind? Is it just bad timing?"
More like suspect manners and one wishy-washy dude! It's cool if he needs some space or is up-front that maybe you guys are just going to get together once in a while and fool around (totally normal and healthy, since it seems you guys are pretty casual at the moment), but saying he doesn't have time for you in front of you but not TO you is a weak-ass look. I think the more important question to ask yourself is what you want out of him and out of the relationship. You need to communicate clearly what your needs are so he can make a move and a decision.
"How do I convince my boyfriend that a striped tie with a striped shirt is just a no? He also gets offended when I gently tell him his clothes don't match!"
Well, in order to give you the best possible advice, I'd actually need to see the shirt and tie in question. Maybe it's not so terrible! But maybe he looks like the front of house at a Guy Fieri restaurant in Orlando. I dunno. If he is a more entry-level dresser — and it sounds like he is — maybe you can inform him that bolder ties pair best with more understated shirts, like a plain blue or white pinpoint oxford. If he doesn't buy that because he wants to fly his pattern-clashing freak flag, he can also try a gingham (small check) shirt and a striped tie, but that's more Advanced Italian than he might be capable of pulling off. Workable, but takes a little practice. If he still won't listen to you, his foolish looks and the lack of respect that go along with them will be its own punishment. Just tell him to wear a plain shirt, yo.
"Where is the best place to meet guys? I'm talking old-school strangers. No Internet dates, no friends of friends, coworkers of friends, sibling of friends — I've drunk from that well too many times. I'm pushing 30, and I want a Hollywood moment. Is it possible to just meet some guy I don't know at a coffee shop or bar? If possible, how should I go about it? Should I approach guys or wait for them to approach me?"
I applaud your romanticism and really want to help you find someone nice, so here's some topline info that I can pass along: While it is possible to meet your dreamboat dude randomly, I wouldn't go out cruising for a date to go along with your oat-bran muffin at the coffee shop or your double-vodka soda at the local watering hole. The reason people in the movies can go from counter to couch in under 30 minutes is because, well, you know the answer. Totally fine to approach guys, just put yourself in their shoes and make it light and flirty. If there's a spark, it will present itself. If that doesn't work, friends of friends really is the best method.
Photo: Courtesy of Elliot Aronow