If hanging out with someone makes your skin crawl, and they try to use guilt to get you to go out with them in the first place, you can rest assured that it's probably not gonna get better from there.
There's a massive difference between being creepy and just being weird. Tons of people are weird, but typically weird people know that fact, and they are able to let their weirdness manifest itself as dorkiness, quirkiness, or at the very least, eccentricity. But there's a vast difference between being super into medieval history and being the type of person who makes people want to take a shower after meeting you.
And don't go thinking there's a deeper integrity to someone's terrible creepiness. It's a lot safer to assume that people wear their intentions on their sleeves, so when someone who you just met seems to know a lot more about you than what you've actually told them, don't go trick yourself into thinking that it will get better.
Here are some folks who went against better judgement and dated creeps. And here's a delusional nice guy who went bananas on an engaged coworker.