While I kind of get the overall tactic (and it just might work!), the idea making a move after lots of eye contact once she’s already outside strikes me as incredibly creepy. This would also depend on the nature of the neighbourhood/outdoor space, since not all bars and clubs are on really busy roads - some women might find this to be rather threatening.
I think the line between “cute, finally making a move and respectful of minimizing awkwardness” and “dude took all night to finally come over, followed me outside and is now saying he wants to get to know me…stalkerish” is a fine line indeed. I think someone who can’t figure out how to get past “Hi” in a conversation should NOT be trying this technique. It’s not for amateurs!
Start with “Hi, how are you?!” Then extend your hand and introduce yourself. Her natural response will be to introduce herself. Whatever her name is say, “oh what a nice name!” And then let the conversation flow… ask her about herself .. make small jokes (but keep them clean) and ask her questions that are not Yes or No answers. Engage her answers… soon she will be asking you questions. Above all be yourself and don’t be a creeper.
I always start with some innocuous line about the shared environment. “The bartender’s making them strong tonight.” “Who sings this song?” “I wish it weren’t raining.” “It’s packed in here tonight. More than usual.”
Then ask her an open question about something you’re thinking about. That way, she has to give you a response, but you’ll have an easy time following it up since the topic’s already in your head. Last night, you could’ve said “So what’s your zombie apocalypse plan?” If the response is a dead-end, you can easily switch gears with something like “Do you really think people would start looting and shooting so quickly? Or would they try to band together in big groups?” The important thing to remember is that it doesn’t necessarily have to be related to anything contemporary.
After that comes the jokes. While some women like geeks and some like athletes, the one thing they all (and men, too) have in common is they like people that can make them laugh.
Finally, you seal the deal with what I accidentally discovered is the best line in the history of lines- “Y’know, my house is right across the street from here.” Bam! She feels safe. She can walk there. She can get back to her car in the morning. Her friends know where she’s going. If you live across the street from the bar, the panties are coming off, my friend.
Good tip! Because her answer might help you think of another question. She might even ask you questions. And you’ll have to answer them. Next thing you’ll know, you’ll be chatting up a girl!
No no no please please do not follow a girl you don’t know outside. At a club, at the mall, at the grocery. That is absolutely terrifying.
(This is different if you are both already outside for a legit reason, but the idea of someone following to your car or to a dark parking lot really sets our alarms off.)