What your most awkward dating experience?

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 lol


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What Girls Said 4

  • For me it was probably whenever my ex who was 13 years older than me & I went out. People normally thought were were siblings, so we got quite a few stares or comments when we made it obvious that we, well, weren't.

  • I had a dating awkward/cheater relationship. He was living with his friend and his friends girlfriend. We were together for 4 months and I found out the whole time he was cheating with his best friends girlfriend.. And they got married 😂✌

    • yo that some fuck up shit lol some people just don't care.

  • Finding out he'd cheated on me when I tested positive for chlamydia!

  • Well I was supposed to go out with this guy, he was 3 hours late, because he was sleeping. He begged me to go out with him and so I gave in. He said he'd pay for me if I came back.
    I got there and he was completely atrocious. He was rude to me, he compared me to a boy, he kept talking about other girls he was gonna go out with, and to top it all off he was talking about this homeless guy that he knows that would be a great match for me.
    When the date was over, he opened his wallet and he had only enough to cover his meal, so I had to pay for mine when he promised to pay for me.
    Then he had the audacity to ask me if there would be a second date.
    This was the most awkward night of my life; I was so uncomfortable.


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