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00:00I love being unqualified and giving advice. It is my favorite pastime. Literally love it.
00:08Hi friends, it's Lilly Singh. My new movie Doing It is all about awkward firsts,
00:12tough conversations, and navigating love, dating, and everything in between.
00:16So the Page Six staff sent in their juiciest questions because let's be real,
00:20no topic is too awkward for me. So let's do it. All right, let's see what kind of freaks we got
00:26here, shall we? Dear Lilly, I want to spice things up in the bedroom, but I don't know how to bring
00:30it up without making it awkward. Any tips? Starting off with a bang. Listen, I feel like the best way
00:39to do this is passive aggressively. I truly believe that in my heart. Don't be direct. Watch a movie
00:44that has a really spicy scene in it and be like, what do you think about that? Wouldn't that be cool
00:49if we tried that? Like, I think that could be cute. Like, should we order some stuff right now and then
00:53just have it ready on your phone to pull in order some stuff? But I just feel like comedy is the
00:56best vehicle, you know? Sometimes you sit down and have a super direct conversation. Like,
00:59mostly I believe in being direct, but sometimes I think you can be playful and be like, should we
01:03try that? Should we do that? But also, what do I know? My sex life sucks. Dear Lilly, my partner and
01:10I have totally different sex drives. How do we meet in the middle without making either of us feel
01:14guilty? Ooh, this is a great question. I did read somewhere once that if you don't want to, like,
01:20put yourself forward because you feel like you might get rejected because there's different sex
01:24drives. You could have, like, a code. I'm very big on codes. So sometimes what people do is they have
01:28a candle on the night table and if it's lit, that means someone's in the mood. And that way, if you're
01:32not in the mood, you don't have to, like, say verbatim. You just, like, kind of, I guess, blow out the
01:37candle, which honestly would devastate me, so I don't know if that's going to work. But I feel like if you
01:41had some sort of code, instead of just saying it verbatim and making the move verbatim, maybe it's a code
01:46word, maybe it's a code gesture, maybe it's like a certain top, whatever it may be. Some way where
01:51you can kind of, like, align without saying it directly. Dear Lilly, my partner always wants the
01:57lights off during sex, but I feel insecure that it's about me. Should I bring it up or let it go?
02:02Baby, it's not about you. Sex is awkward. Nobody wants to see that with the lights on. It's not about
02:07you at all. I definitely think you should bring it up and you should ask because I feel like
02:11communication is the key to sexy success. I feel like you should be like, babe, can we try with the lights on?
02:15And they're probably gonna be like, I bet you they feel insecure, but it has nothing to do with you.
02:20We're always busy thinking that it's about us because we're self-centered beings and I get it.
02:24I think everything's about me all the time and often it's not. No one actually cares about you or me.
02:29Good luck! Dear Lilly, I've been with my boyfriend for a year, congrats, but we still haven't said I
02:34love you. Should I be worried? A year? Now here's the thing. Baby, let me be real with you. I'm into girls.
02:42We say I love you on the second date, so I can't relate to this at all. You know what I'm saying?
02:45Three months, we're moving in with each other. Some stereotypes are true. Not saying I love you
02:50in a year? I think the question is, do you feel it and you haven't said it? Because I think after a
02:55year, if you felt it, you should just say it regardless. And whether he responds or not,
03:00I think that will be very telling for you. So I think you should say it. And don't do this whole,
03:04the guy has to do everything first. It is 2025. You can say, I love you first. You can propose.
03:09Not that you should after a year. I don't think that's, I think you need to wait. But I'm just
03:12saying you can make the first move and see how that goes. But I would say after a year,
03:16you're due for an I love you. You deserve that. You deserve an I love you. I think every couple's
03:20counselor and therapist is going to get fired because I'm doing their, this is basically,
03:24you should send me a tax receipt. I'm basically, this is basically charity work is what I'm doing
03:27right here. Dear Lilly, I want to wait until marriage, but my friends make me feel like I'm living
03:31in the wrong decade. How do I stay confident in my choice? Let me talk to you, okay? My whole life,
03:37I felt awkward about this. I've always been quite sexually reserved. I was raised to also believe
03:42to wait until marriage. I have since changed my choices about that. But I always used to feel
03:47awkward or bad. I need to tell you that you should feel so empowered in your choice. Sex has no timeline
03:52other than the one you believe in. You can have sex with everyone. There's no right or wrong age or time
03:57and no one around you should make you feel bad about it. And if they do, you need better friends.
04:00I'm going to have to put your friends on the line. Let me call your friends. Friends, you need to be better
04:04friends, okay? It's your body. You get to decide what you're doing with it. There is no timeline,
04:09baby girl. You do you. Dear Lilly, how do you tell someone you're not interested after a first date
04:14without ghosting? Use ChatGPT. Like, it's real simple. No, I actually do not believe in ghosting.
04:21I have never ghosted someone in my life. I think there's nothing a little communication can't handle.
04:26Hey, I had a really good time. I want to be really honest. I don't feel like I see anything here,
04:32but I think you're such a lovely person. I wish you the best of luck. And then you throw that sucker
04:35into ChatGPT and you say, make this warm. Make this not hurt the person's feelings. Throw a couple
04:39emojis in there. Boom. I think communication is one of the most respectful things you can do.
04:42I do not think anyone should be ghosting. With all the methods we have to communicate,
04:46ghosting is not okay in 2025, in my opinion. Dear Lilly, my parents keep asking when I'll settle down and
04:53get married, but I'm not even sure I want that. How do I shut down the pressure? I'll tell you what I did.
04:57I just found so many ways to disappoint them that they don't even ask me these questions anymore.
05:02Like when you shock your parents so many times, they just give up. I'd say do whatever you can
05:07to make your parents give up. They clearly still have faith in you and that's your first mistake.
05:11You know what I mean? That is your first mistake. Me, I was like, I'm gonna start making YouTube
05:14videos. I'm gonna move to LA. I'm gonna be an actress. I'm queer. I dress like this. I'm gonna get
05:19tattoos every week. I just did a bunch of things and now they're like, we have no faith in Lilly and we
05:23don't think she's ever gonna get married, so we should stop asking her. And it's worked out well.
05:26Dear Lilly, my partner and I have totally different love languages. Is it possible to make that work
05:31long term or will we always feel mismatched? I love this question because I'm a big believer
05:36of love languages and I believe one of the biggest mistakes we make is loving other people how we
05:40want to be loved as opposed to how they want to be loved. So it is okay for you to have different
05:45love languages. For example, my love language is acts of service. I want people to do things for me
05:49all day long. A task, help me with my schedule, whatever it may be. My love language. Someone else's love
05:55language could be physical touch. My mistake would be doing acts of service for them because that's
05:59how I want to be loved. It's okay if it's mismatched but you just have to get better at being like,
06:03what do I want versus what they want and they're not the same thing. That's often where we get
06:08confused and so I do believe it's possible and I think it's very common for people to have different
06:12love languages. Dear Lily, I caught my friend's partner on a dating app. Do I tell them and risk
06:18drama or stay out of it? I have never had a more clear answer in my life. Hear me when I say this.
06:25Put this card down. I'm gonna cross my legs right here. If this could zoom in, I would make it zoom in.
06:30Editor, make it happen. If your friend is cheating on someone and you do not call them out on it,
06:38you are a bad friend. Friends who let other friends act whack, you are bad friends. I, anytime
06:45I've seen my friend do something questionable in their relationship, I've been like, you, come here.
06:49I cannot allow you to be this way. You are too good of a person to be this way and I make them come
06:54clean. So you should absolutely call your friend out and absolutely make them do the right thing.
06:58We're not out here being mid. We're out here being evolved. Evolved folks, okay? Said what I said.
07:03Dear Lily, I've been single for so long that I feel awkward even flirting now. How do I get my
07:08confidence back? Hashtag relatable. Straight up. When I first went on dating apps after I was like,
07:14I like girls, I literally would message girls and be like, hey sis. And I was like, that's not right.
07:19I should, that's not, that's not right. So it takes a while. But I would just say, I think that
07:25awkwardness during flirting is very endearing. I think everyone's a little nervous and everyone's a little
07:29awkward and I think it's okay to be human. I think you don't have to flirt like how anyone else flirts.
07:33Flirt like how you flirt. And if that's nerdy and awkward and quirky, that's amazing. You'll find
07:37someone that really, really likes that. Trust me. I'm a huge nerd. I flirt while talking about my vision
07:42board and I get some action here and there occasionally. Dear Lily, I'm in a long distance
07:48relationship and the lack of physical intimacy is starting to get to me. How do I make it work?
07:55Yeah, this is a real thing. As someone who's been in some long distance relationships,
07:58this is a really real, real thing. I would say, this is the really honest answer I'm going to
08:03give you. You need to work hard and book some flights. That's the only way. You can FaceTime,
08:08you can text, but I think when you're in a long distance relationship, there has to be energy
08:12and commitment from both people to understand that there's some effort and energy that's going to be
08:16required here, which means you got to work some overtime. You got to put some money in the piggy bank.
08:20You got to book those flights. You got to earn those points and you got to get to wherever you get to
08:23to see them because it is important to see each other as often as you can. And so
08:28you might have to become a baller. Side hustle, catch those flights. You know what I mean?
08:33Listen, how much do you love them? Spirit Airlines does exist. You know what I'm saying? There's always
08:37an option. All right, page six. What else you got? Give it to me. Dear Lily, my ex texted me,
08:42I miss you. Ooh, messy. In the middle of the night. Ooh, messy. Do I ignore it or see if there's something
08:49still there? Well, baby, this depends. Do you miss them too? Are you lying next to someone or are you
08:54just riding solo, wiping your browser history? Where are you at in your life? It depends. I think
09:00if you miss them too and if they didn't, like if you guys, this is just levels to breakups. Do they
09:05cheat on you? If they cheat on you, I don't think they deserve a second chance. If they like just kind
09:09of naturally stop talking, it depends. If you miss them, I'm a big believer of saying what you mean.
09:13I think life is too short to hold in your feelings. If you miss the person, text them. You miss them back.
09:18Don't let pride or ego get in the way. Sometimes people are right for each other but not right for
09:22each other at that time. And if this is a different time, maybe you are right for each other. But it
09:26depends what they did and it depends the situation you're in. But if you're lying next to someone who
09:30treats you well that you're obsessed with, do not text them back at all. Capiche? Dear Lily,
09:36my cultural background is really conservative, hashtag relatable, but I don't share the same views about
09:41dating and sex. How do I bridge that gap with my family? I really relate to this. I was raised in a
09:47pretty conservative family when it came to sex and dating. In fact, the concept of going on a date
09:51is foreign to my parents. My mom, I don't think, has ever been on a date. My parents are actually
09:55virgins. I've never gotten the talk and this was never discussed in my house. And for a lot of my
10:02life, I was like, sex is bad, sex is wrong. You have to wait till marriage, yada, yada. And then there
10:06came a point in my life where I, as an adult, had to make a decision of how I want my life to be and
10:10what I actually believe and what my, what my timeline is. And I'm a big believer that when
10:17it comes to sex and even living with someone I would say is a bigger thing for me, I do think
10:21it's important to do before marriage. I want to know what someone is like in bed, in a house,
10:26in life before I commit my life to them. And so that is my belief. But there comes a point,
10:31it's actually an episode of Shameless, the show Shameless. There's a really good scene where the
10:35characters are standing on the front steps of their house and he just says, there comes a time when you're
10:39an adult and you have to decide you don't want to be like mom and dad again or you don't want to
10:44have the trauma of mom and dad again or anymore. And so I just encourage you that you got to live
10:48for yourself. You got to live for yourself and they'll get over it. Dear Lily, I've been dating
10:52someone for a few months and I like them, but I don't feel fireworks. Do I stick it out or cut it off?
10:58Fireworks? What rom-coms are you watching? Fireworks? Who feels fireworks? Fireworks are scary.
11:04Things get set on fire with fireworks. They're bad for the environment. What is this fascinating with
11:08fireworks? The fireworks thing is interesting. I think sometimes we watch too many rom-coms or for
11:15me Bollywood movies where there's a certain idea of love that is a little bit unrealistic. I agree
11:20someone should give you slight like nerves and butterflies and stuff, but this whole idea of like
11:25I'm willing to do such drastic things for someone. I mean, let's just be realistic also.
11:29Maybe you don't have to feel fireworks. Do you feel like a like a slight candle? Like a slight flame?
11:35A slight spark? Maybe not fireworks. Let's just, times are rough out here, okay? We're lonely. You need to
11:41lower the bar a little bit maybe. Dear Lily, I'm in my 40s and recently divorced. Dating apps feel
11:46overwhelming. Where do I even start? I get it. I get it. Um, dating apps can be super overwhelming.
11:52Meeting people in person can be super overwhelming. I go back to at the age of 30s and 40s and 50s,
11:58you've lived life to this point where like you've probably pretended to be so many different people
12:01at this point. Just be yourself now. Whether it's on an app or in person, just be yourself. I think
12:06apps can be stressful because you're like, what's my opening line? What is this game I have to play of
12:10like how long do I wait before I message again? When I'm on apps, I don't play any game. I say exactly
12:16what it is I want to say. I don't care about lines. I don't care about this waiting period. If I want to
12:20do something, I do it. So can you just operate from a place of what do I actually want to do and actually
12:24want to say? Operate from there. Dear Lily, I caught my partner snooping through my phone.
12:29Should I be mad or wonder what they're hiding? Caught my partner snooping through my phone? Okay.
12:36In my opinion, there is no greater betrayal than someone going through your phone. I am of the
12:42belief, if I ever saw someone going through my phone, that would be an unforgivable offense to me.
12:46That is such an invasion of privacy. I would definitely, I would be mad. I would be mad. They would have to
12:52apologize. That's like passcode being changed. Also, like how'd they get into your phone? You're
12:58half to blame here. How'd they get into your phone? It doesn't matter if you don't have anything to
13:01hide. Phone is an invasion of privacy, is my belief. They shouldn't be going through your phone.
13:05There should be trust there and I think you should address that 100%. That's not cool. It's not cool.
13:10Dear Lily, how do you know when you're actually ready to have sex versus just feeling pressured to check
13:15it off a list? Ooh, great, great question. I don't even know if I, to be completely honest,
13:21there's times when I have felt pressured. I think it's really normal, especially,
13:25especially when I say as a woman, but I'm sure for all people, to feel pressured to have sex
13:29now and then. I think I always just go back to my operating system. Every day when I wake up,
13:35I'm like, where do I want to operate from? Do I want to operate from a place of fear and pressure
13:38or from a place of what I want? I think if you're going into an intimate situation, just to kind of flip
13:43that switch in your brain to be like, my only rule for myself is to honor what I actually want.
13:49That is my only rule. What I found myself doing is because I operate out of such fear, I go into
13:55a situation and automatically I'm like, I'm not going to have sex. I'm not going to do this with
13:58this person. And I set that hard boundary. Then sometimes I'm with the person and I'm like,
14:02they're kind of cute. Why did I say all that? If I could just operate from a place of like,
14:07honor what you want to do in the moment, I think we'd be all better off. I think none of us are
14:12particularly good at that. We have all these things going on in our mind. Don't overthink it. Just do what you
14:16want to do in the moment and what is right for you. And that is all the advice I've got for you today.
14:21Now whether you're single, taken or somewhere in between, remember, love and sex look different
14:25for everyone. And there's no one right way to do it. Bye!
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