What is/are some of the most awkward dating experience you had with someone? weather it happened on just a date or the hole experience of being with that person, what about it made it so akward?
Mine would have to be when I was seeing an older girl, she 38 I was 18, and she had a son who was 22. So every time I saw him it was awkward being that if things got serious between us, I would have a step son who was older than me.
Most Helpful Girl
Nothing terrible. Story time:
2011. After four years, I finally worked up the nerve to ask my crush on a date. Senior year homecoming. I drove from my house to his to pick him up (and almost bailed and turned around about 17 times from nerves). I crossed a street, let's call it Main Street, to get to his house.
I pulled into his driveway, picked him up, and then got the directions out for the restaurant. The directions began with, "Turn right on Main Street," and my flustered ass FORGOT where Main Street was or that I fucking crossed it on my way to his house lmao
So the first five minutes of our date were me freaking out because I was lost hahahaha
That was embarrassing and he was judging hard. BUT... let it be known... HE didn't know where the street was, either :p
We're engaged now so I guess our two direction challenged butts are gonna have a hard time lol0