How to Go on a First Date During Quarantine

Definitely, I have— every single night before I go to sleep, and then right when I wake up in the morning, I would say those are the two times I’m most confident that I will never find love. [MUSIC]

I went on a run the other day. And I tried to make eyes with someone. But I had, like, a bandana on. And it was just like, what does that even— nobody can see my expression. It was like, yeah, I don’t know what it’s going to look like. [LAUGHS]

Is this your first speed date ever?

No, I did it for Valentine’s Day with two— some of my friends in 2018, and it was a disaster. So—

The whole idea lately has been like, how do we stand out? How do we make this exciting? How do we not sound like another dating app?

Let’s see. They just complained. Is that about you? I was not prepared for that question at all, you know, too kind, too giving, too empathetic.

I used to smoke way too much weed, actually. But I haven’t smoked weed in over four years. So that has been rectified.

The end goal for me is not to get somebody married. I know that that’s out of my control. But what’s in my control is to help someone enjoy being single and help someone enjoy their dating experiences, which, I think, is so important when it comes to dating and something that’s really missing in society. As a single person today, you’re just expected to meet someone. And the journey to get there is not going to be a great journey. You just have to kind of get there.

You said this phrase that kind of blew my mind, which is, I want them to enjoy being single.

Yes.

And that’s, for me, at least, such a reframing of the entire dating industry.

Yes.

You know, I remember, gosh, maybe 10 or 15 years ago, when online dating was just starting to happen. And there was so much taboo around it. You know, I’m half Indian. Are you— do you have a South Asian background?

Yes, I am fully Indian.

You’re fully Indian.

Yeah.

And I remember dinner conversations with friends basically saying, it’s not that different from an arranged marriage system in the sense of having filters that ease the way, right? Like a matchmaking— it’s actually still that same filtering sensibility, except the location of choice is in the individual not in the family.

Right.

What’s really interesting about what you just said is that feels countercultural to what a dating company is for.

Mm-hmm.

And I would bump up that language a lot.

OK.

If you elevate this part of why you do this as a company, which is, you want to give people an ability to enjoy being single and enjoy the journey, it frees your format. Enjoy being single is a radical idea, right? It’s a business-defining idea. It’s a— it will make you less money, I mean, at some level. It just changes the goal of what anyone thinks the goal is. And you know, I’m married. When I hear you say that, I relax. I exhale. It’s like, oh, thank god. Right? It’s like you’ve changed the goalpost. The goalpost is a meaningful experience with other people.

Yeah.

What’s interesting is you actually have access to people’s homes immediately, right? And you can give a lot of information, if they’re willing to share it. Like, what does someone’s kitchen look like? What does their fridge look like? Right? Open your fridge right now. Is there a beer bottle in it? Or is it stuffed with veggies? There’s a lot of ways to play with the current location that people are actually in, right? We are all zooming in from our most intimate spaces.

I love this idea. I like that as an icebreaker that doesn’t take 25 minutes, but everybody starts— or even, you know, tonight’s speed-dating event is in your kitchen, or on your couch, kind of like an insight into your home life.

So much of dating is, like, masks, and so much of connection, meaningful connection, is unmasking.

Yeah.

And I think you, as a host, need to have judgment around how much do you unmask too fast. Part of desire and part of mystery is actually not— is the journey to get to know a person. And so maybe you don’t want to see the fridge right away. That’s where your expertise needs to come in. I’m going to read you one more tweet that was on that same thread that I think will delight you and perhaps spark other ideas. It’s a little risque, but I loved it.

OK.

So In that same thread line, a guy named Jimmy Riss tweets back at Aaron. And he says, “I was at a Zoom party. And at the end of the night was maybe eight folks in the, quote, ‘hot tub room.’ Everyone was in their bath at home.”

Oh, wow.

“All chilling the hot tub together. And it turned into naughty truth or dare. And it was a rad and unprecedented, for me, experience that felt natively digital.”

That’s super cool. I’m like, forget speed dating. Like, I’m doing that tonight. [LAUGHTER]

And I was thinking, what’s in your house round, or what’s in your—

Like, should we do a show and tell?

—dwelling. Yeah, oh, love it.

OK, cool.

And I was thinking, what’s on your bedside table? Or what’s a book on your bedside?

Or what’s in your bedside drawer?

What did you— oh, yeah, yeah, exactly. Exactly. Heighten the risk. What’s in your bedside drawer? What’s in your fridge?

And then, I don’t know if this goes into a different category, or if there’s, like, a digital round, but, like, what’s the last song that you played?

The last website you were on maybe.

Oh, that’s interesting. That’s so good. What’s the— open your search browser. That’s actually kind of hilarious.

Oooh. Like, the last five or three or five or 10 sites that you visited.

That’s so good. And I’m starting to get nervous.

Because that’s so true, Like, read out your last text message.

[LAUGHS]

[INAUDIBLE] we’re laughing. It’s so good. Oh, what about, like, what dating apps you have on your phone? It would give someone an insight [INAUDIBLE].

That’s true. How did this person really spend their time.

Yeah.

You know, I think part of dating is not a full unmasking on the first date. But I think this is a really interesting way for people to see more quickly a person’s actual lived reality.

Right. Yeah. Because very quickly, like, you could know if my last five phone calls are family members.

Yeah.

There’s also— someone who really knows me would know this about me. And you can just go deep really fast.

That’s lovely. What’s the most meaningful object in your home. Bring it to the screen. I think that what would you take with you right now, people could easily default to, like, my favorite water bottle, versus just like, what’s the most meaningful object in your home, they may think a little, and realize, actually, it’s a letter from my grandmother. You know what I mean? I want people to be able to just pause for a second and not just bring objects of use but objects of meaning.

Yep.

A relationship could blossom. A friendship could blossom. So it should be an experience for you guys. You should really just have fun with it. Relax and enjoy. My name—

But on the dating apps, I feel like I leave it kind of open, just because I don’t want to kind of limit it or something. I don’t know. Deep down, I do want that connection and a partner, so an equal, somebody that I can feel activated by, somebody that excites me.

I have a decent amount confidence just in myself in terms of, like, what I can bring to a relationship and what I can bring to somebody else’s life. And I think that I have a lot of great career ambitions.

You know, I officiated a wedding last September. And in the wedding officiant speech, I spoke, about, bell hooks and her definition of love being just spiritual growth that you kind of go on with somebody, and just that enrichment, the idea of, like, making someone’s spirit grow and become stronger through the course of a partnership, I think, is the thing that I’d be looking for, and honestly, not something I’ve had in many, many years.

I think I’m just such a romantic, I need the alignment of certain stars that are so impossible. And I’ve just fully committed to being alone if that alignment doesn’t happen.

I think I just want to be blown away by someone who I’m also, like, holy shit, this person is, like, far more brilliant and like, accomplished, and like, ambitious. And you’re physically blown away. And if you were in a coma, you would trust all my decision-making capabilities. And— and I love you a lot. If I don’t get those four stars to line up, I’m like, [INAUDIBLE] I’ll be the cool uncle.

Question number one, what’s the post-COVID trip you want to take.

Yeah, I really want to go to Japan.

Same.

Really?

Yeah.

OK.

I was planning on going in September.

Name all the dating apps that are on your phone. This is so easy for me. Right?

Is it— OK.

None.

Dammit.

[LAUGHS] I have no dating apps on my phone.

[CLEARS THROAT]

Well, I mean, so let me clarify. I argue that Instagram and Twitter are actually the best dating apps.

You’re sliding into DMs?

I think I’m back in here. Turn my video on please. Oh.

Hi.

Hello. This is my face.

[LAUGHS]

OK.

My video’s on.

My video’s on. Hello, Kyle.

[INAUDIBLE] over there.

Huh?

You’re a supermodel. How are you?

Supermodel?

Oh, gosh, read out your last five texts you sent out.

Oh, shit. Oh.

OK, they’re almost all embarrassing.

[LAUGHS] Yeah, go ahead.

Uh, one is, “I can’t believe I’m doing this. Why did I say yes so easily?”

Someone— oh, “will send mom something for Mother’s Day.”

Nice.

That was to my sister.

What is it going to be?

I don’t know. So I need to figure that out yesterday.

Another is, “do you know Yahyra?” [LAUGHTER]

And then this one was, I said, “I’m a bike vibe.” Because I told— [LAUGHS] I told my friends that I have my bike. I say, “I got my bike back in case anyone’s running today.” And then I said, “I’m a bike vibe.”

Sick.

I don’t know what that was supposed to mean. But it was supposed to mean, like, if y’all are running, I can bike beside y’all because that’s, like, the vibe I’m going for.

Yeah. That’s definitely the vibe.

Right?

Yeah.

What’s in my fridge? I would say we usually have a lot of oat milk. I like it for coffee.

I don’t know. Can you see it? Can you see what’s in the fridge?

Yeah.

There’s some beer. There is— I usually have eggs.

I see one bottle of beer. I wouldn’t call that some.

No, there’s five, six.

Oh. I think that’s what you have the most of.

Yeah, I would say that. I would say I probably have the most beer. Tortillas maybe? Tortillas are pretty good. They’re flour.

Oh, dude. Wait, is that from the Bushwick spot?

[? Dekumbe, ?] yeah.

Show me the reading material in your bathroom? How did— see, this is kind of creepy. How did they know I had reading material in the bathroom? Does everyone have— do you have reading material in your bathroom?

I have a [INAUDIBLE]. It’s, like, an art piece. But yeah.

I actually—

But I don’t read it. It’s kind of funny.

OK, so we’re now in my bathroom.

OK.

We’re now going to toilet. I’m not using the toilet.

OK, great.

But this is this little candle. Ignore that.

Boring.

This is the only reading in my bathroom. This is The Motivation Manifesto, Nine Declarations to Claim your Personal Power. I started reading that. I never finished it.

[LAUGHS] So you weren’t motivated?

No.

This is interesting. This was a skillet. I bought it— well, let me tell you this first. I ought a skillet from Amazon. And it turned out to be fucking— can you see how big that is?

[LAUGHS]

Do you see— like it came— I wanted— first I had this box. And I was like, I came to my door. And I was like, did I order a shield? Like, why is this— why is it so large? What is this? And then I opened it, and it was that fucking skillet. And I’m like, I wish you could see me cooking in it because like— wait, hold on. Maybe I can show you. Like, when you turn— [CLICKING] There we go. OK. When you turn on, like, the burner, right? it doesn’t even cover this part.

[LAUGHS]

So, like, let’s say you’re making things on here. You’re like, oh, I can use this entire area. No, you can’t because this side—

Is colder.

This side is cold. And I’m like— so literally, I turn on two burners—

[LAUGHS]

There’s a middle burner that I turn on to catch the side stuff.

(LAUGHING) Oh, my god.

Are you laughing? What happened?

Oh, you weren’t there.

No.

Oh, my god. He bought this skillet that is so big. It’s— it was cracking me up. He, like, put his hand in it for a reference. And it was— it looked like just this small, like, Brussels sprout compared to, like, the surface area. I was laughing. [LAUGHTER]

That’s also— laughing is a great sign at the end of the date.