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The Viall Files

E1090 Ask Nick - 50 First Dates and Still No Boyfriend

09 Mar 2026

Transcription

Chapter 1: What is discussed at the start of this section?

0.115 - 23.178 Nick Viall

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23.198 - 41.022 Nick Viall

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41.423 - 62.59 Nick Viall

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62.57 - 73.532 Nick Viall

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73.933 - 92.45 Nick Viall

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Chapter 2: What challenges does the caller face after 48 dates?

1124.458 - 1139.721 Nick Viall

They want to put the work and they're going to be, of course, they're going to be honest. I'm not going to lie. I'm not going to lie about it as a cheater because that's what I used to do in the past. And then imagine a lot of people being like, well, I'm sorry. Once a cheater, always a cheater. And I've been cheated on before. You know what I'm saying?

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1140.021 - 1160.73 Nick Viall

Probably a very similar kind of feeling that you might feel, right? And this is all to say, like, you're not alone when it comes to those types of feelings. And I think everyone on some level will always, again, feel rejected, right? For similarly, and I, yeah, I really believe that. I think, you know, people might not like us for whatever reason.

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1160.79 - 1179.478 Nick Viall

Maybe there's not their type, you know, and I would, I would guarantee that whoever of the majority of those men who you felt rejected by, it was neither the experience or the weight loss. It was just, I don't know. She's just not my, she's just not my person. That, that, that I'm, that I'm certain of.

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1179.458 - 1194.578 Allie

Well, there's something interesting to me with all these experiences that I'm trying to figure out, like, how do I get better at this in the future? And maybe there's not a way to do that, but it's like, I've had, and now with this last one, five of these experiences where we get like two months in.

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1194.678 - 1201.146 Allie

And so it's not like they go on one or two dates with me and they find, you know, something about my personality or my personality.

1201.126 - 1230.272 Allie

future goals that's not going to work they like give me a few months and then once i think the stuff about weight loss or like things get more physical and they like figure out what that means like like it does feel like kind of funny to me that it because if it was something that was just personality and incompatibility why are they stretching it out that long well i don't think you get to know someone in two months to me earlier i don't know i i i imagine it's a it just feels funny because it's been like about the same time

1230.86 - 1237.047 Nick Viall

Like, are you, is that like the same time you're like taking clothes off and, and, and, and hooking up and, or like.

1237.628 - 1252.907 Allie

Kind of. And I mean, another part of this, which is a whole other tangent is that I'm also a virgin for like, which probably was clear, but that is like a whole other thing too, with like the inexperience and the weight loss. I mean, I guess, but it doesn't need to turn off.

1253.187 - 1268.151 Nick Viall

I think that's really only a turnoff to the degree that you make it a big deal. And I understand that it probably is a big deal to you, but I don't know, in your case, your virginity is, I'm guessing, centered around just your lack of dating experience.

Chapter 3: What advice is given about managing friendships in difficult relationships?

1268.992 - 1282.568 Nick Viall

Yeah. Which makes sense, right? It's not, you know, it's not some, you didn't make some like big decision, you know, you weren't like saving yourself for marriage or, you know, it just didn't happen. So the more you make it a thing, the more it's a thing.

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1283.442 - 1290.711 Nick Viall

You know, I don't know if this applies to anything you're thinking or feeling, but literally last night, have you heard of the black coffee theory?

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1291.512 - 1308.152 Nick Viall

Okay. I saw this on, I saw this on Twitter. Don't know if it relates to you, but I was really like, that's fucking great. So apparently like the black coffee theory goes something like this. A guy goes into a coffee shop and he wants a latte, but he goes up to the front desk. He's at the Starbucks and he's like, and she goes, what do you, so can I take your order?

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1308.272 - 1327.269 Nick Viall

And he goes, all I know is I don't want a black coffee. And she's like, I don't like, well, what do you want? He's like, I don't want a black coffee. I just all I know is I don't want a black coffee. And she's kind of like, OK, I guess. And then she kind of like, you know, has a bunch of other orders. It's chaotic as coffee shops often are.

Chapter 4: How should the caller communicate her dating inexperience?

1327.41 - 1335.218 Nick Viall

And then it's time to get to serving this man his order. All she can remember is black coffee. So she just brings him a black coffee.

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1335.653 - 1354.586 Nick Viall

And the premise being is this, like, if you focus on what you don't want in your life, whether you speak it out loud or say it to your friends or the people you're on dates with or internalize those thoughts and feelings, that will still be the thing that, you know, brings that shows up in your life because that is where your energy and thoughts and feelings are going and things like that.

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1354.646 - 1370.548 Nick Viall

And it was like a really profound thing that I was just like, that's so like, I don't know how it applies to me, but I'm sure. But where your energy goes and what you fixate on. And if you fixate on what you don't want, you will still probably get what you don't want more often than not. You don't want to be a virgin anymore.

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1370.629 - 1397.964 Nick Viall

You don't want to feel rejected by men who are judging you for having a different weight in the past. You don't want men to judge you for your lack of experience or whatever. If that's where your thoughts and feelings are going, it will probably show up. in that way. And so a lot of, I'd be willing, you know, like, of course you're going to meet judgmental people in life.

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1398.304 - 1414.345 Nick Viall

Yes, some people are going to, you know, no matter what, you know, judge you for that. But how you internalize that and how you process that and how you move through the world will play a bigger role on how often that shows up. I mean, I really think that's true. Yeah.

1414.527 - 1433.266 Allie

Yeah, no, that is a good point. And I think it kind of gets at maybe what's underneath all of these things. I think with dating, because there are judgmental people, I feel like maybe my mindset or the way I'm showing up is that, okay, I feel like I have all these things working against me. I'm a virgin. I don't have relationship experience.

1433.326 - 1444.977 Allie

I used to look a lot different a few years ago and went through weight loss and have loose skin. And so I feel like I'm always on the defensive with that. And maybe that's coming back. Yeah. Across.

1445.178 - 1454.829 Nick Viall

I mean, listen, I I've, I've talked to you for 15 minutes now. You're a beautiful person. You seem like you have a great personality. You're like, you, I don't know. I don't, you seem smart, you know, like you have a presence, you know?

1456.033 - 1456.093

Um,

Chapter 5: What advice is given for handling difficult friendships?

3566.876 - 3568.598 Haley

But yeah, yeah, exactly.

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3568.618 - 3591.321 Nick Viall

You're like, you can't do this thing around. Here's a book. Read it. You can't do this thing around. Find a therapist, you know, and that's all good advice and well-intentioned, no doubt. But I think she's had enough of that. Lately, I have been getting back into some books and some literature that, you know, has helped me in the past and I've kind of revisited it.

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3591.561 - 3591.782 Unknown

Yeah.

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3592.142 - 3605.664 Nick Viall

I'm doing that because I wanted to. I felt ready. You know, I wasn't like, no, I have never in my life read a book that someone's told me to read. I don't like to read. I'm dyslexic. So like no one, you know.

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Chapter 6: How can you support a friend in a toxic relationship?

3605.704 - 3606.525 Unknown

Yeah.

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3606.86 - 3632.756 Nick Viall

She's like, I have a book you should read. Great. Good for you. You know, they might look at the cover, turn the back, you know, but like she'll, she'll do it when she's ready. But when she's ready, you want to make sure that she has a belief in herself. And when she looks in the mirror, she is kind of like, what the fuck are you doing? And that will only come from you leaving out the but.

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3632.957 - 3633.958 Haley

That's fair.

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3634.699 - 3654.432 Nick Viall

And I would challenge yourself the next time you get on the phone to leave that phone call feeling connected to your friend, inspired by your friend, feeling good, feeling better. than when you got off. And I think if you bring that energy to that phone call, I promise you, you will feel different.

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3654.612 - 3664.947 Nick Viall

Because right now, when you get on the phone with your friend, you have an assignment that you've knighted yourself. And then every time you get off the phone, you feel like you failed. You feel like you failed yourself.

Chapter 7: What are the signs of a friend who is not ready to change?

3664.967 - 3673.941 Nick Viall

You feel like you failed your friend. She doesn't hear you. She's not listening. And it's very frustrating for you. But you have to let go of that.

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3674.225 - 3687.525 Haley

Yeah. And just lead with love a little bit more. Yeah. I mean, do you think it's fair to kind of level set with her and almost just have that open conversation and just say like, just almost remind her, like, I love you and I'm always here for you?

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3688.306 - 3717.478 Nick Viall

No, I would. I think this is something you need to work on. And I think I would I would I would challenge yourself that this is. And this is not something you are doing to trick your friend in a way. You really have to let go of the outcome. And I think this is you recognizing that well-intentioned or not, that you haven't shown up for your friend in the way that she's needed you.

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Chapter 8: How can you set boundaries with someone who keeps ghosting you?

3717.458 - 3742.081 Nick Viall

And you want to challenge yourself to do a better job of that. And so I think you just really start slow. This is new for you. This is something you need to practice. This is not about you crafting a new delivery, you know, so that your friend receives what you're trying to say. Because if you do that, you will put some kind of artificial timeline on that.

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3743.083 - 3753.642 Nick Viall

It'll be like, all right, I'll try this thing this fucking Nick guy said. All right, I'm going to, you know, in the back of your mind, you'll be like, I'll give it 10 phone calls. And then that 10th phone call, when she doesn't change, you're going to go back to your old ways.

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3753.622 - 3782.683 Nick Viall

And I think if you really work on this and recognize this is something you need to change, not only with this friend, but just maybe in all aspects of your life that, you know, when you have an expectation from a friend and you leave that call feeling worse, you know, I would think about, you know, what you brought to that call and, and what your expectations were going in, you know, type of thing, especially if, if, especially someone like yourself who can recognize that you are the tough love friend and,

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3782.832 - 3812.383 Nick Viall

And as a tough love friend, I think we all need to work on is when that tough love is needed. And it often isn't. And I think sometimes when it comes to friendships, us tough love people could listen a lot more and just try to connect with our friend. Your friend has not felt a connection with a friend or a phone call in a long time. She has just felt lectured.

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3812.363 - 3813.245 Haley

Yeah.

3813.265 - 3815.87 Nick Viall

And so I would really, I would really focus on that.

3816.25 - 3825.067 Haley

I was just going to say, I feel like, yes, but at the same time, probably because of how I've responded in the past, it's almost like, we just don't talk about it now.

3825.528 - 3825.728 Unknown

Yeah.

3825.748 - 3833.443 Haley

Like call me the other day, you know, it wasn't about him or a situation. If I ask how he is, it's like, good. We're working on things kind of just

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