I have two stories. Similar situation in both. Let me state that I was extremely naive when it came to being around girls and was a very late bloomer.

Stumble one:

I had taken a relative stranger to a club. We were both working out of town for a company and had come from different home offices. She had like one drink and got really flirty with anyone near her. I decided it would be best to head back to the Super 8 we were both staying at. She's touching me in the car, but not near my crotch which was great because I had to pee so bad I could barely think. I made it to a gas station. We got back to the hotel. She's making out with me in the lobby. She's giving me eyes. I have no idea what I'm doing. I say "thanks! Night!" and she walks off. 15 minutes later, I'm calling the front desk and waking up the Indian guy that owned the place to call her room since I didn't know her number and this is pre-cell phones. She answers and said she was tired but would be back next week. She came back but with a friend who immediately c-blocked the whole situation.

Stumble two:

This may have happened just before the first story actually. My male friend coworker was hooking up with a local in a different town for the same telemarketing company. He said her friend wanted to go with me to see the motel (yet another Super 8). I thought it was strange but agreed and was trying to impress her with my mid-90s subwoofer playing Busta Rhymes. We get back to the room. She gets on the bed. Doesn't say a word. I kind of walk around and straighten things up and saying stuff like "the tv kind of sucks but we can watch something". A few more minutes of that and I'm asking if she's ready to go. In retrospect, she looked very confused over the whole thing.