Cuffing season: Why singles look for love during the holidays

Kat Kentrell's thoughts on this, dating expert, matchmaker. Good morning. Nice to see you. Good morning. Nice to see you both. Yes. Okay, yeah, you walked in during the commercial break. We were chatting about this, and Ron said, you know, we should probably continue this convo. Yes. He's 70. How old is she, Ron? I'm like 26. 26. Yeah. Yeah. And I heard some ladies saying, oh, that's gross. There's too much, too far. And I said, you realize that a lot of men look at that situation and says, They say, go for it. Well, and I'm thinking, Kat, he's 70 years old. Let him live his life. Sure. You know, what are your thoughts on this, though? I... My only, well, I have a couple of reservations about it. So when we talk about large, so that's what we would say in the industry, a large age gap relationship. Where does it get large, though? I would say if it's beyond 12 to 15 years, it starts to kind of venture into that category. So what should you be on the lookout for then? So the thing is that as a matchmaker, when you have... multi generations in between the two the question becomes what is first off how are you really truly relating to one another is it just physical is it just or are you both like in it for the future of the both of you so sometimes what happens in larger gap relationships is that the relationship usually becomes more about the older's partners Goals, aspirations, dreams, those types of things. And what we find is that in larger gap relationships, the older partner becomes more of like a paternal role with the other person. So it can cause some. That's something. Issues. But do they generate within the relationship or outside forces? Both. Like you said, if there's multi-generations in between, you might have a son or a daughter or a nephew or a niece who's like, this can't happen kind of a thing. How do you navigate that? That is something that when we do have people that come forward that want larger gap relationships, one of the things that we put into perspective is, okay, so imagine yourself talking to this person's parent. Like put yourself in their shoes and what is your relationship going to be with their parent? Because most likely their parent is going to be your age. Or you could be their grandparent. That's right. You know, potentially. Yes. Okay. Well, we covered the ground on that one. There's my two cents. Maybe he was looking for a granddaughter. Maybe he was like, I need another granddaughter. Well, and some people will say that people are just looking, that they're looking for someone just to take care of them and kind of become their nurse and their caretaker and that kind of thing. Oh, interesting. So, yes. Okay. But generally speaking, if the older person is wealthy, you shouldn't marry for money. No, absolutely not. Because eventually, I mean, People will object and say, well, it's their prerogative and they can do it. And yes, absolutely, if that's the arrangement. But the majority of the time when men come to me about this specific question, they want her to really date him for who he is. And I always have to tell them, in most cases, That's not going to be the case. Would you say, of course, no names or anything like that, but does it work one time out of 10 or one time out of two? I mean, what are your odds? I mean, you always will have outliers with everything, right? I mean, I wish that there was black and white when it comes to dating and relationships, but there really isn't. So let me ask you this. So maybe there's somebody in the chat who's a billionaire, okay? And they're thinking, I want to go out and I want to date. Yes. So should you maybe like, Drive an older pickup truck and wear flannel and jeans and some work boots and go out like that and then test the waters and see if she likes you. It's honestly not. As long as he's still authentically presenting it as himself. That's correct. And not. Or presenting himself in a way that is not true to who he is. Because you can have the flip where they have the saying in Scottsdale, right? The $20,000 millionaire. Oh. Where are they? Yeah, where they're acting like they're big shot. Right, that's right. But really they're not. Are there a lot of those? Pretend big shots? Yes. Oh, shame on you. Shame on you for trying to pull the wool over everyone's eyes. I will just say, this reminds me of a situation years ago. We had a very attractive female anchor here who was not married, and I remember an older guy at the gym says to me, hey, why don't you tell so-and-so that I would love to go on a date with her and tell her I got a lot of money? And I thought to myself, no, I'm not going to do that. If that's your sales pitch, date me because I got a lot of money. Who did that? That probably works with some women, though. Yes, it does. Unfortunately, right? Yes, it does. Absolutely. I mean, and a lot of those men are okay with that. They're okay to have that arrangement. But the most of the men that I talk to that come to me, they're really looking for companionship and long-term relationships. So we love this combo. We want to continue it. Yeah, yeah, yeah. You did come on to talk about cuffing season. I did. What is that? So cuffing season runs from, it's a saying in our industry, that runs from... October to February in which couples are purposely putting themselves out there to find a significant other for this, this particular season. So they're cuffing together. So to go through the holidays together. So, cause there's a lot of pressure for single people around this time when they go home and they're like, Oh, you're still single. Or I have this person to set you up with, or why is somebody like you still on the market? And so they get a lot of pressure from friends, from family and it's cozy. It's fall. So people want to cuddle more They're more optimistic about love and relationships. Hallmark movies are coming out. So people are more open to the experience of being with somebody. But what I always tell people is that, okay, if you're going to date somebody, If you're dating them in November, is this the same type of person that you would be dating in June? So, but is there an agreement when you meet somebody during cuddling season? Like, Hey, I don't think they know that that's what they're doing. They just, they don't say anything about it. So like, they're not like, Hey, I'm, you know, come mid January. I'm out of here. No. I think it just naturally when you're on the verge of Valentine's day, that's usually they don't even, Oh my gosh. The audacity. Right. I know. Getting, dumping them before Valentine's Day, Ron. It's a real thing. Is it driven by these, by Thanksgiving and Christmas? Yes. And also Valentine's Day? Yeah. It could be anywhere in that season. It could be anywhere, right. I mean, they just did a survey in 2025 in which almost 80% of Gen Z and 70% of millennials admitted that they are. looking for a specific relationship during this time. That's a big number. It's huge. Wow. Yeah. So it's, it's something that we talk a lot. And so when people come to me and like one of my busiest months where people are like, Oh, this is, nobody's really dating at this time of year. There's a lot of people dating. December is actually my biggest month of the year. So how does your job work? This is kind of interesting, right? So, so somebody calls you, let's just say we're single, but we're not right. But we are. Yes. We're single. Do I call you? Men call you? Women call you? Yes, both. Hey, Kat, you know, December I have a lot of travel with family. I'm looking for somebody to hang with. And then how does it work? Yeah, so what we do is put them through a multi-step process, but really it starts with the consultation. Because I've had, I mean, this is Scottsdale and Phoenix, where I have had men just... fly in for the weekend and contact me and like, Hey, do you have somebody for this weekend? Like for tonight? Oh, you know, that's a different service. I'm like, this is not the type of service I run. It's, it's multi-step for a reason. We want to make sure that people are dating with intent. We want to make sure that when, especially when hiring a professional, that they're in the right head space and the right heart space to make sure that, okay, I'm dating with intent. What is it that I'm really seeking in a relationship? What is it that's really for finding somebody for long term. And so when people come, we... To do a consult first, because I always say the first match you have to make is the one with the matchmaker. Well, you know, Celeste and I, in all seriousness, we are trained in this business to look at both sides of everything. Yes. And so you'd be a little bit skeptical by nature. Absolutely. We're talking about cuffing season, but as we get to the holidays, for a lot of people, I would say most people, their stress level actually rises. Yeah. Is that the right time to be looking for a relationship? I think. If you think about what you're having to endure during the holiday season, a lot of people are looking for that partner to give relief the pressure, right? And we all know that in the early stages of dating... it's what, you know, the honeymoon period is. So it creates optimism and positivity. So even though you're having stressful relationships with family, or you're having to endure the holidays with people that maybe you don't want to spend with, but if you have somebody that you really enjoy by your side, it makes it that much more tolerable. Like, hey, you know, you had a bad, maybe the conflict at the Thanksgiving dinner or something like that. And then you're like, you know, we're going to go out and grab a drink. That's right. Or we're going to go for a walk. Yeah. And then you take that person with you. That's right. That's right. And you're not alone. That's a great question, though. Right. We're almost out of time here, but we were going to, every morning at 6:45, Celeste does this great segment. It's called Celeste Story of the Day. Yeah, I love it. And today, Celeste, you were talking about if people are spending more and more time on their phone. Yes. Gradually, they're spending, the phrase was digital dementia, but gradually you're stepping Jumping further back from... Normal interactions, social interactions, no matter what age you are, any perspective that you would have on that? Oh, digital, it's ruined really meeting people in real life. Like, even if you think about going to the airport, sitting on an airplane, waiting in line for coffee, even waiting in your car for coffee, any point in time that people are having to wait, the first thing they do is bring out the phone. They don't, or either that or they're plugged in, right, so they have earbuds in, and we talk about it all the time, How do I meet people in real life? Well, first off, take those out. Make eye contact. Make eye contact. Put the phone away. I mean. Even in online dating, people are swiping and spending 14 hours a week. Oh, my gosh. Swiping? Swiping. If you could spend 14 hours a week out at the coffee shop or somewhere else meeting somebody at the dog park or whatever you fancy, you might actually meet somebody. That's right. You know? And I always tell people, don't leave it to the other person. You have to be able to present yourself being open. If you're going to go to a coffee shop and sit at a chair and not make eye contact and have your, you know, have your laptop open or. Then you're not approachable. You also have to be approachable.