Q. What’s one thing
I should never ask him
on a first date?
A. OSHER: ‘You can
ask anything you want!
Just never ask a question
you’re not prepared to
hear the answer to. If
you don’t like an answer,
think about what you
make it mean – because
if they have no problem
with answering, they
have no problem with
COMPILED BY MEL EVANS. PHOTOGRAPHY BY BEN HANSEN/BAUER. STYLING BY DENIS TODOROVIC. GROOMING BY CARLA MICO. STYLIST ASSISTANT: ANA ZUPANOSKA. the answer either.’
MATTY J WEARS
T-SHIRT: NEUW AT GENERAL
PANTS CO. JEANS: WRANGLER AT GENERAL PANTS CO.
OSHER WEARS
JACKET: KSUBI AT GENERAL PANTS CO. T-SHIRT: GENERAL PANTS CO BASICS. PANTS: H&M. BAUER SYNDICATION ©
SHOP TIL YOU DROP; ISTOCK
Q. HOW DO I
KEEP IT COOL AND
CASUAL ON THE
FIRST DATE?
A. OSHER:
‘As someone who
doesn’t drink, [when
I was dating] I would
find things to do that
didn’t involve a bar
or booze. I always
enjoyed something
as simple as a walk
or a coffee, some-
thing while the sun
was up – that way
there would be no
pressure to carry on
to something where
expectations might
increase.’
MATT Y: ‘First dates
can be quite difficult,
especially if you’re
really into the person.
A lot of people pick
a bar or restaurant
for a location but I
find they can be a
little awkward. As
simple as it sounds,
I really like the idea
of just going for a
coffee. If you hit it
off you can always
extend the date into
a lunch.’ #
Q. I like double dates
- I get nervous, other-
wise. Is that a turn-off?
A. OSHER: ‘Think
about the reverse of
the situation. You’re
comfortable because
you’re with two people
you already know and
one new person. But the
other person is meeting
one they barely know
and two strangers. It’s
way worse for the other
person and I’d suggest
that you bite the bullet
and stick out the one-
on-one.’
MATT Y: ‘I don’t mind
double dates. Sometimes
it’s a bit less pressure
when you meet some-
one for the first time in
a group as there’s less
risk of awkward silence.
Although I do think it’s
important to not always
find safety in numbers
- it’s really key to have
time together when it’s
just the two of you.’
MATT Y: ‘ Sorry, I’m
going to disagree with
you here, Osher! I know
it’s important to be open
but I think there are a
couple of subjects that
shouldn’t be brought
up on a first date. For
example, asking how
much money they earn
at work, the number of
people they’ve slept with
or details about their ex.
There are just so many
other things to talk
about on a first date.’
‘OK, I WAS NOT
PREPARED FOR
HIM TO SAY THAT!’
COSMOPOLITAN SEPTEMBER 2017 147
sex & relationships