W Magazine Videos

"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

Credits

Starring: Molly Shannon, Greta Gerwig, Anderson Cooper, George Mackay, Rebecca Hall, and Chloe Sevigny
Featuring: Erik Maza
Director: Marina Valle
Executive Producer: Harris Levinson
Editor: Jessy Price

Produced by: Emoticon Productions

Transcript

00:03
Dates that I didn't know were dates.
00:06
And then you have this moment at the end,
00:08
and you're, like,
00:10
What?!
00:11
Oh no!
00:14
And then I've gone on dates where
00:15
they didn't know it was a date.
00:19
Which is hard in a different way.
00:21
It was
00:23
in college, I actually went on a date
00:26
with a woman,
00:26
which was a rarity.
00:27
And I don't know.
00:28
I sort of was, like,
00:29
You know what?
00:30
Yeah, I should go on a date. Why not?
00:31
And it was this very attractive lady,
00:33
woman, college student.
00:36
But I sort of wanted to test her out.
00:38
I kind of did.
00:39
I doubted why she was dating me
00:41
and I thought maybe she was, like,
00:42
knew who my mom was
00:44
and kind of thought that was cool.
00:46
I went to Tony Roma's Ribs with her.
00:48
'Cause I thought,
00:49
of all the places,
00:50
that would sort of be a good trial.
00:52
If she complains about being
00:53
in Tony Roma's Ribs,
00:55
probably not a person
00:55
I'd want to hang out with.
00:58
And, yeah, date didn't go anywhere,
01:00
and it was a disaster.
01:02
Yeah.
01:03
I've had some friends
01:04
that have had to come with me
01:06
as, like, third wheels,
01:07
which was kind of awkward.
01:08
I remember having a Valentine's date
01:10
at Windows on the World
01:11
and my friend didn't have a date.
01:13
I was, like,
01:14
Alright, you can come with us.
01:15
(laughs)
01:16
It was more awkward for her
01:17
than for me, I guess.
01:18
My first
01:19
was a long time girlfriend,
01:21
so we ended up working out alright.
01:23
But it was when I was at school.
01:26
We went to the cinema
01:27
for the first date
01:28
and just sort of leaning in
01:29
and missing a kiss.
01:31
I literally, sort of, kind of,
01:33
just missing it.
01:34
I don't really know how you can do that.
01:35
But I managed it.
01:36
Having a comedy Valentine's date
01:38
when I was in my twenties where
01:40
two friends and I decided to
01:41
go out to a restaurant where
01:43
everyone was coupled up.
01:44
And we just sat there
01:46
and did this whole performance of
01:48
this really functioning happy threesome.
01:51
Just to annoy people.
01:52
(laughs)
01:53
It was kind of funny
01:54
I had an awkward date.
01:56
I was on an afternoon date
01:58
with a playwright.
02:00
I was pretty young.
02:01
I was 22 so I didn't
02:02
have that much experience.
02:03
He took me out on a boat ride
02:04
near Marina Del Rey
02:05
and we had Chardonnay.
02:05
And then I had to tell him that
02:07
I had to get back because
02:09
I had a babysitting job or something.
02:10
And he go so angry
02:11
and I was in the middle of the water on a boat.
02:13
And I was, like, He's gonna kill me.
02:14
(laughs)
02:15
I thought this was gonna be like Dateline, you know?
02:17
He got so angry.
02:18
And I'm stuck in a boat with him.
02:20
Crush on a girl in high school.
02:21
I bought her a Hello Kitty teddy bear
02:24
for Valentine's Day.
02:25
And I never talked to her.
02:28
So that was-- That's a good gift.
02:29
Very embarrassing.
02:30
[Interviewer] Did it work?
02:31
No, not at all.
02:32
I don't know.
02:33
I haven't really had a great Valentine's Day yet.
02:36
I think it's a lot of pressure
02:37
on one day.
02:38
I'm not sure I agree
02:39
with the whole Valentine's Day concept.
02:41
I like to try to
02:43
work those days in
02:44
the rest of the year.
02:45
[Interviewer] Right. Every day is
02:46
Valentine's Day--
02:46
Yeah For this guy.
02:47
Yeah, it's true.