"My Most Awkward Date"
As Valentine’s Day approaches, a few actors, from Greta Gerwig to Nick Jonas, recall their most awkward dating stories.
Released on 2/11/2016
|Starring:||Molly Shannon, Greta Gerwig, Anderson Cooper, George Mackay, Rebecca Hall, and Chloe Sevigny|
|Executive Producer:||Harris Levinson|
Produced by: Emoticon Productions
Dates that I didn't know were dates.
And then you have this moment at the end,
and you're, like,
And then I've gone on dates where
they didn't know it was a date.
Which is hard in a different way.
in college, I actually went on a date
with a woman,
which was a rarity.
And I don't know.
I sort of was, like,
You know what?
Yeah, I should go on a date. Why not?
And it was this very attractive lady,
woman, college student.
But I sort of wanted to test her out.
I kind of did.
I doubted why she was dating me
and I thought maybe she was, like,
knew who my mom was
and kind of thought that was cool.
I went to Tony Roma's Ribs with her.
'Cause I thought,
of all the places,
that would sort of be a good trial.
If she complains about being
in Tony Roma's Ribs,
probably not a person
I'd want to hang out with.
And, yeah, date didn't go anywhere,
and it was a disaster.
I've had some friends
that have had to come with me
as, like, third wheels,
which was kind of awkward.
I remember having a Valentine's date
at Windows on the World
and my friend didn't have a date.
I was, like,
Alright, you can come with us.
It was more awkward for her
than for me, I guess.
was a long time girlfriend,
so we ended up working out alright.
But it was when I was at school.
We went to the cinema
for the first date
and just sort of leaning in
and missing a kiss.
I literally, sort of, kind of,
just missing it.
I don't really know how you can do that.
But I managed it.
Having a comedy Valentine's date
when I was in my twenties where
two friends and I decided to
go out to a restaurant where
everyone was coupled up.
And we just sat there
and did this whole performance of
this really functioning happy threesome.
Just to annoy people.
It was kind of funny
I had an awkward date.
I was on an afternoon date
with a playwright.
I was pretty young.
I was 22 so I didn't
have that much experience.
He took me out on a boat ride
near Marina Del Rey
and we had Chardonnay.
And then I had to tell him that
I had to get back because
I had a babysitting job or something.
And he go so angry
and I was in the middle of the water on a boat.
And I was, like, He's gonna kill me.
I thought this was gonna be like Dateline, you know?
He got so angry.
And I'm stuck in a boat with him.
Crush on a girl in high school.
I bought her a Hello Kitty teddy bear
for Valentine's Day.
And I never talked to her.
So that was-- That's a good gift.
[Interviewer] Did it work?
No, not at all.
I don't know.
I haven't really had a great Valentine's Day yet.
I think it's a lot of pressure
on one day.
I'm not sure I agree
with the whole Valentine's Day concept.
I like to try to
work those days in
the rest of the year.
[Interviewer] Right. Every day is
Yeah For this guy.
Yeah, it's true.