Conan Gray writes the kind of songs that make you cry in the club, but on this episode of “Blind Date,” he’s all sharp takes, dry wit, and emotional honesty. Over vodka cranberries (a not-so-subtle nod to his single) and carrot cake, the ‘Wishbone’ singer-songwriter opens up to Cosmo Editor-in-Chief Willa Bennett about his dating dealbreakers, why he friendzones his love interests, and how his best friendship with Olivia Rodrigo sometimes gets in the way of their music career.
Stream Conan's album, 'Wishbone' here: https://conangray.lnk.to/wishbone
Shop the Wayfair set here:
Table: https://fave.co/4nxIz8s
Chairs: https://fave.co/4pSKPsq
Lamp: https://fave.co/476CSZl
Side table: https://fave.co/3KRAZaf
Curtains: https://fave.co/3KxoWyO
Cherry blossom: https://fave.co/4862NS2
Orchid: https://fave.co/4nvjVVY
#ConanGray #Wishbone #VodkaCranberry #BlindDate #Cosmopolitan
Stream Conan's album, 'Wishbone' here: https://conangray.lnk.to/wishbone
Shop the Wayfair set here:
Table: https://fave.co/4nxIz8s
Chairs: https://fave.co/4pSKPsq
Lamp: https://fave.co/476CSZl
Side table: https://fave.co/3KRAZaf
Curtains: https://fave.co/3KxoWyO
Cherry blossom: https://fave.co/4862NS2
Orchid: https://fave.co/4nvjVVY
#ConanGray #Wishbone #VodkaCranberry #BlindDate #Cosmopolitan
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PeopleTranscript
00:00Who is a better kisser, role model, or Cory?
00:05Um, well...
00:06My name is Willa Bennett, and today I'm going on another blind date.
00:10I have absolutely zero guesses for who it is.
00:13So, wish me luck.
00:25Hello?
00:26Hey.
00:28What's up?
00:30I feel scared.
00:33Okay, you're giggling.
00:34You're flirting with me.
00:35Mm-hmm.
00:36No.
00:37Oh, okay, okay.
00:38Don't worry.
00:39What do you do for a living?
00:40I write songs.
00:41What do you write songs about?
00:43My questionable love life.
00:45Oh.
00:46Questionable love life.
00:47So, you've been on dates that aren't with me.
00:49Have we met?
00:50Yes.
00:51Long history.
00:52So, you write songs about dating.
00:54When was your last breakup?
00:56Year and a half.
00:58Um...
00:59Are you single right now?
01:00Yes.
01:01How single?
01:02Ish.
01:03When was the last time we saw each other?
01:04Two months ago.
01:05Okay, numbers.
01:07Woman in STEM?
01:09Are you Chaparron?
01:12No.
01:13Uh, are you...
01:14Olivia Dean?
01:15No.
01:16Am I, like, kinda close or no?
01:17You've gotten the gender wrong.
01:19Role model?
01:20Yes!
01:21No, I'm kidding.
01:22No, no, no, no.
01:24But you know role model.
01:25Yeah.
01:26And I saw you two months ago.
01:27Mm-hmm.
01:28And you just had an album come out.
01:29Mm-hmm.
01:30Bone in Gray.
01:31Aw.
01:33Dude, your outfit is so cute.
01:35Your outfit is cute.
01:36We're honestly kind of matching.
01:38I love your album.
01:39I was listening to it all weekend.
01:40Thank you, Ella.
01:41It has been two months.
01:42It has been two months.
01:43Addison Rae.
01:44Yes, Addison Rae, The Box.
01:46The Box is a really, really, really interesting place in New York City.
01:50And Addison Rae had her party there to release her album.
01:55I actually saw on TikTok this weekend that you were one of the first people to listen to Diet Pepsi.
02:00Is that true?
02:01I think I was the first person ever.
02:03Wow.
02:04Yeah.
02:05I didn't even know you guys were friends.
02:06Well, at the time, we barely knew each other.
02:08I was in the studio that day just hanging out.
02:10And I walked in on their session just to say hi.
02:14And then they had just the chorus.
02:16Wow.
02:17And they were like, oh, I don't know how I feel about this.
02:19They, like, played it.
02:20And I was, like, listening.
02:21I was like, oh, this is a hit.
02:23I knew.
02:24I was like, this is a hit.
02:26Okay, cheers.
02:27Cheers.
02:28Oh, my God.
02:29I'm gonna drink vodka cranberry with Conan Gray.
02:30This is, like, my dream date.
02:32I love your album.
02:33I remember the last time I interviewed you, you had told me that you had never been in a relationship before.
02:38And this one, you have been.
02:39What's the difference for you making music?
02:42It's very different, for sure.
02:44I think when I was younger, I looked at relationships and I was very, like, oh, you don't love me, well, you.
02:50Like, but now it's like, oh, like, you don't love me.
02:53That's okay.
02:54I feel this way about it, but I also feel this way about it.
02:57Is there anything that that taught you?
03:00To stop liking emotionally unavailable people, probably.
03:04So true.
03:05So true.
03:06Cheers to that.
03:07Word.
03:08Word.
03:09What's your first date move?
03:10Like, do you actually go to dinner?
03:12Do you get a drink?
03:13Oh, my God.
03:14Do you drink?
03:15I drink much.
03:16I'm not, like, sober.
03:18Like, but I just, I get in interesting situations when I drink at all.
03:22Really?
03:23I'm also, like, a very not fun drunk.
03:26My drunk is not, like, woo-hoo, like, I'm drunk.
03:28I'm literally just, like, I need to take a nap.
03:30I need to take a nap.
03:31I need to take a nap.
03:32Like, I'm, like, so exhausted.
03:34And I also say stupid shit.
03:37Like, one of my most memorable moments, I just played Coachella.
03:40And I was hungry after, you know?
03:44So I, like, go to, like, the stands.
03:45Everyone's, like, oh, let's, let's have a gin and tonic to celebrate.
03:48I, like, drink the gin and tonic.
03:49I'm feeling fine.
03:50And all of a sudden, like, next thing I remember, I'm, like, talking to the people who are, like,
03:55actively making me pad thai.
03:57I'm, like, in, like, behind the counter, like, in the kitchen, like, talking to them.
04:01And they're, like, oh, like, like, do you like this food?
04:04And I'm, like, I love this place.
04:07I go here all the time.
04:09I had never been there.
04:10You would not drink on a first date?
04:11No.
04:12No.
04:13Second date?
04:14Maybe a second date.
04:15My first date move is a coffee.
04:17Classic.
04:18Cause, like, I don't know if I know, I don't know if I like you.
04:20Like, I don't know if I want to be around you for, like, a whole, like, two hours.
04:24But then coffee, it's, like, you going for a walk?
04:26Like, you sitting there?
04:27Oh, I don't know.
04:28I guess.
04:29Go for the, I go for the walk.
04:31When was the last good first date you've been on?
04:33Three months ago.
04:34It was, it was just one drink.
04:36Wow.
04:37Yeah.
04:38And no, no contact hints.
04:39Didn't know that well.
04:40No.
04:41No.
04:42Bound to never speak again.
04:44Okay, this is a really fun part of the show where I go through old Cosmos for their first
04:50date advice.
04:51And you can tell me what you think.
04:52Okay.
04:53See how it aged.
04:54Based off Cosmo, July 1988.
04:55Is he a find or a friend?
04:58One, how do you know if the man in your life is Mr. Right or just Mr. Right now?
05:03Ooh.
05:04Uh, whether you're comfortable or not.
05:06That's a really beautiful answer.
05:08But sometimes crushes make you not comfortable.
05:10But, like, sometimes crushes make you, like, so uncomfortable that, like, you can't really,
05:13like, breathe or, like, function as a human being.
05:15And, like, that's probably not the one.
05:17Probably not.
05:18Does that ever happen to you?
05:20You're like, do you listen to my music?
05:22It's Friday night and your guy wants to veg on the couch, but you've got your heart
05:27set on the dance floor.
05:28Sounds like something you do.
05:29Sounds like us, right?
05:30Oh, so us.
05:31Literally us at the box.
05:32Oh.
05:33Us at Addison Rae's release party at the box.
05:36So what do you do?
05:37I'm on the couch, bitch.
05:39The couch is so much better.
05:42I never need to go out ever anywhere.
05:45I kind of agree.
05:46Is it a red flag if someone goes out all the time?
05:48Sometimes if someone goes out, like, way too much, as in, like, is, like, genuinely not
05:52taking care of themselves as a human, like, that's definitely a red flag.
05:55Like, what about your future?
05:57What about your longevity?
05:58What about your bone density?
05:59What about your lung health?
06:01Your bone density?
06:02Yeah.
06:03You check for that?
06:04Bone density's important, guys.
06:06We're young right now, but we won't always have strong bones.
06:09You won't always have strong-ish bones.
06:11Yeah.
06:12Yeah, quote that.
06:13Quote that.
06:14How do you feel when a guy you're seeing brings up past fling?
06:17If it's, like, a first date or a second date or a third date, run.
06:23Like, run so fast.
06:24Really?
06:25Yeah, especially if it's, like, oh, my gosh, like, oh, my exes are crazy.
06:30What's the common denominator, babe?
06:33It's you.
06:34How would you feel if your lover has frequent out-of-town work trips?
06:39Well, you can't talk, Mr. We're wide.
06:41I really can't speak on that.
06:44Like, if you're dating me, just the reality is, like, I'll see you once every five or six months, maybe.
06:50It's, like, an online relationship.
06:52I'm just, like, kind of in my, like, Gmail era, I guess.
06:56I like to keep things classic.
06:59Okay.
07:00Would you swoon or cringe if your boyfriend made you a mixtape?
07:03I think that's sweet.
07:04What do you think?
07:05I love it.
07:06Yeah.
07:07Listen to it 50 times.
07:08Yeah, and I'd be like, this is all about me.
07:09I love it.
07:10You're listening to the lyrics, and you're like, what are they trying to say?
07:12Oh, 100%, because that's what you're doing, right?
07:14If you make a mixtape for someone, you're trying to send a message.
07:18What if they put your music on it to you?
07:20I would be flattered.
07:22Aw, that's sweet.
07:23What's your favorite song you've ever written?
07:25I think that my favorite on Wishbone right now is Class Clown.
07:30It just hurts so good.
07:32Yeah.
07:33Yeah.
07:34I just read how, like, when you and Olivia send music back and forth, like, you're always wrong about it.
07:38We've always been wrong about each other's songs, and we knew that.
07:41Like, literally always.
07:42Why do you think that is?
07:43I was so interested in that.
07:45I think it's just too biased.
07:47Like, we know too much about each other's lives, right?
07:50I think with, like, a friend, to get a really good analysis of, like, what you're doing in life,
07:55like, doesn't matter whether you're, like, making an album or, like, you're working on some work project,
07:59you kind of do need the advice of strangers.
08:01Hmm.
08:02Because if those are the people who are consuming what you're making, like strangers are,
08:07then, like, you should know their taste.
08:09And sometimes you're just too close to the situation.
08:11Interesting.
08:12So were you surprised that Vodka Cranberry was a single?
08:15I wasn't.
08:16But I think if it was up to Olivia, it would have been My World.
08:19Oh, My World's so good.
08:21I love my, that's my second favorite.
08:23Okay.
08:24Nauseous and My World are my favorite.
08:25ClassCon I need to listen to again.
08:26I really like it.
08:27Those two are Liv's favorite.
08:28But Bob, oh.
08:29So you have Liv taste.
08:30That's so cool.
08:32And you apparently said, I don't know about Vampire.
08:34Okay.
08:35Which is iconic.
08:36At the time that she played me Vampire, she'd written a lot of the rest of Guts already.
08:41So I heard so much of Guts and I was like, love this album.
08:44Love, stream, download, buy.
08:46So then by the time she played me Vampire, I was like, there's so many good songs.
08:50Like, I don't know.
08:51Like, I don't know about this one.
08:53But we've always been wrong about each other's songs.
08:56And we knew that.
08:57Two more questions.
08:58What's your biggest deal breaker?
08:59Drugs.
09:01Are you whispering?
09:04Drugs.
09:05Like, hello?
09:07Finish the sentence.
09:11He's a total dreamboat, but.
09:13He does drugs?
09:14I don't know.
09:15Literally.
09:16I don't know.
09:17No notes.
09:18That's perfect.
09:19That was perfect.
09:20Thank you, my dear.
09:21Okay.
09:22How are you meeting people?
09:23Apps?
09:24Um, how?
09:25No.
09:26I think mutual friends is the best way because they're pre-vetted.
09:30Have you been on a blind date?
09:31I have.
09:32Okay.
09:33Story time.
09:34It was nice.
09:35And then it was over.
09:36Okay, so it was one date.
09:37Yeah.
09:38But I think blind dates are having a resurgence right now, and it makes sense to me.
09:43It makes sense to me, too.
09:44I think, in reality, you really can love, like, a lot of people.
09:50Would you ever be in a polycule?
09:52Personally, no.
09:53Yeah, me either.
09:54But that was giving poly energy.
09:55It was stressing me out too much, but.
09:57You're like, I can love so many different types of people at times.
10:00I'm open.
10:04Carrot cake.
10:05Do you like carrot cake?
10:07I do.
10:08Oh.
10:09I feel like you don't love it as much as I do.
10:13These are blind reader questions from Cosmo Readers.
10:16Okay.
10:17Are you more likely to friend zone or be friend zoned?
10:19I feel like this goes against what people think of me, but I really do friend zone people
10:23quite often, yeah.
10:24Really?
10:25Yes.
10:26Why do you think that is?
10:27Intimacy is scary.
10:28I'm so afraid of being hurt that I also am afraid of hurting people.
10:34Like, you know, it sucks.
10:35I don't want to let people down.
10:37Would you say you're avoidant?
10:38I'm like everything.
10:39I'm like avoidant.
10:40I'm anxious.
10:41How would you describe the feeling of falling in love?
10:44Surprising and peaceful.
10:47Peaceful?
10:48Conan Gray did not say that.
10:51I'm a changed man.
10:53How did you get here?
10:54Wow.
10:55What should I do?
10:56I don't know.
10:57Get dumped really, really hard.
10:58Like really hard.
10:59Do you believe in the one or do you believe in the drama?
11:02Would you ask this?
11:03I feel like those are not like coin flips of each other.
11:06I feel like, I don't believe in the one.
11:09No, I don't believe that there's like a one person in the world for you.
11:13Really?
11:14Not to further your polycule suspicions.
11:17Allegations?
11:18Would you go to couples therapy?
11:21Sure.
11:22Should we go to couples therapy?
11:24I would love that.
11:25What should we talk about first?
11:26I don't know.
11:27I don't know.
11:28Let's unpack.
11:29The polycule allegations.
11:31Okay, this is sweet.
11:32Which celeb couple makes you believe in love again?
11:35Oh, I like cannot comment on this because I don't know what their relationships are like.
11:39Okay, Drew.
11:40Things are never what you think they are.
11:41What about a fictional?
11:42Ooh, fictional.
11:44Luke and Lorelai from Gilmore Girls.
11:47The ultimate slow burn.
11:48Wait, interesting.
11:49Tell me more.
11:50It's like a friends to lovers situation.
11:52That's your favorite trope?
11:53Oh, yeah.
11:54Come on.
11:55Enemies to lovers is so hot.
11:56Enemies to lovers.
11:57We need to unpack that in couples therapy.
11:59Okay, add it to the list.
12:01Add it to the list.
12:02Does it bring you joy that you make so many people cry with your music?
12:05Yeah, it does actually.
12:07I love it.
12:08Who is on your breakup playlist because you're on mine?
12:11That's cute.
12:12On my breakup playlist is Wolf Alice.
12:15They have two that I like really streamed.
12:18One was Don't Do The Kisses.
12:20But my favorite, favorite, favorite of theirs is No Hard Feelings.
12:25The chorus of the song is no hard feelings.
12:28There'll be no bad blood.
12:29Losing your love has been hard enough.
12:31But the one lyric that always gets me is, would we ever have tied the knot?
12:37Well, how long is a piece of string?
12:39And you're like, whoa, I don't know.
12:42How long is a piece of string?
12:43I don't know.
12:44Wow.
12:45Do you listen to like the same songs over and over?
12:47Yeah.
12:48It's like five songs just like.
12:49Okay, this one's funny.
12:50Who is a better kisser?
12:51Role model or Corey?
12:57Um, well, I kissed Corey a lot more.
13:01So I'm going to say Corey.
13:02Sorry, Tucker.
13:03No, this is good because I was worried you were going to say Tucker and Tucker cannot
13:07know that, you know, that can't go to his ego.
13:09His ego is big enough.
13:10Hey, Conan, will you go on another date with me?
13:15Yes.
13:16I will.
13:17Yes.
13:18Thank God.
13:19I'm going to take the rejection.
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