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Host
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Caller 2
Wait.
Host
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Leanne
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Leanne
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Advertiser 2
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Host/Advisor
This is a weird time. If you have just started dating a guy or a woman, it's a strange time as far as presence go, but they mean a lot. Because if you guys mentally aren't the same place, are not at the same place, I should say, then your present is really defining where you think the relationship is right now. You know what I'm saying?
Advisor 1
Yes, Jen.
Host/Advisor
You know what I'm saying?
Advisor 2
Yes. For instance, or if there's a gift at all.
Host/Advisor
Or at all.
Advisor 3
That's gonna be a challenge.
Advisor 2
Why?
Advisor 3
Wondering if there's a gift at all.
Host/Advisor
Well, and what if you do and he doesn't? Or vice versa. There's a. There's a lot of jockeying going on here. So Leanne has a question about a guy that she's been dating for four weeks. Hey, Leanne.
Leanne
Hey, guys.
Host/Advisor
Hi. How are you?
Leanne
How you doing?
Advisor 1
Good.
Host/Advisor
Okay, now, you've been dating this dude for one month, right?
Leanne
Yeah, I mean, we've been named for one month, but we actually. We dated before. We dated last year for about a year. So it's not like I don't really know this guy. We've dated for a year before. But last year, I got this watch for him, and it was kind of like an expensive watch. It was like $800. And so I was going to give it to him for Christmas, but we ended up breaking up before Christmas.
Advisor 1
Okay.
Leanne
And so then I had this watch, you know, and I just, you know, I never got rid of it. I just kind of had it. Well, we started dating again this past November, like, around Thanksgiving. And so since I've had this watch all this time, and I originally bought it for him, and I know him, I'm wondering, can I give him this same watch?
Host/Advisor
Well, that's it. That's a. That's tricky now. And you guys dated for how long? The first time.
Leanne
The first time was about a year.
Host/Advisor
A year?
Advisor 1
Why did y' all break up?
Leanne
I'm sorry.
Advisor 1
Why did you break up after that year?
Leanne
You know, we were just having. We just were having problems. We just, you know, it seemed like everything we did was kind of getting on each other's nerves, and we just ended up fighting all the time. And so we were like, it's better to call it quits right now. And we didn't want to drag that into the holidays and everything. And I think the holidays actually kind of, like, sparked it, because then there was talk about visiting families, and, you know, he didn't really want to bring that into it. And so it kind of just, like, it just blew up at the holiday time.
Advisor 1
Because I think that's important. I mean, I think it's important to note that it was between the two of you. So there wasn't a third party involved. It wasn't any, you know, really dramatic scenario. It was just, you know, what?
Host/Advisor
Deteriorating.
Advisor 1
It was deteriorating. Right. Okay.
Leanne
Okay.
Host/Advisor
So then you guys start dating again four weeks ago. And how serious has it gotten in that four weeks?
Leanne
It's been. I mean, it's been good. I mean, it wasn't. We're not at the point where we were originally. Like, if I. I mean, I wouldn't be buying him an $800 watch, you know, after just dating him for Weeks. So I don't know if that's going to be saying too much, but yet at the same time, because we have this history together, I'm wondering if it's okay because I've just had this. I've just had it sitting here.
Advisor 2
Are you guys.
Leanne
I don't want to be seeing too much at four weeks, and I don't want him to give the wrong idea, but I've had it.
Advisor 2
Are you guys calling each other boyfriend and girlfriend again? Are you exclusively dating?
Leanne
We're not exclusively dating, but we're like, you know, we're together. We actually haven't had, like, the talk about that again. We're just kind of feeling. Feeling things out and getting comfortable with each other again and just kind of testing it out right now. I mean, it's been going good.
Host/Advisor
My knee jerk reaction is to reset the date on your relationship. So if you're only seeing them for four weeks, then treat it like it's a four week relationship, not that you have the year of history behind you.
Advisor 1
Totally agreed.
Host/Advisor
You guys agree with that?
Advisor 1
Absolutely.
Advisor 2
Especially because it's not at boyfriend set. If she had said, yeah, we're boyfriend and girlfriend, I would say, give him the watch. But because. Because you haven't had that talk again and you're not using those labels. Like, he's not introducing you. Like, oh, yeah, this is my girlfriend. So and so then I think it's too much. When's his birthday?
Leanne
His birthday's in the summer.
Advisor 2
Okay, you could just kind of hold out.
Advisor 1
If y' all are still dating, then give him the watch.
Host/Advisor
Then, like, to me, if you're. If you're weighing the two, you could do more risk by giving it to him than by not giving it to him. You know what I'm saying? Here's Brad. Good morning, Brad. You're on Q100.
Caller 2
Hey, guys. Bad idea. Oh, again, I hate the show. But. If I'm that guy, I'm thinking she's trying to buy me. If we only been dates for four months, I'm gonna get the watch and I'm gonna run. So I don't think it's a good idea, just, you know, looking at it as a guy.
Advisor 2
Yeah.
Advisor 3
So you're not gonna, you're not gonna return the watch to her? You're gonna take the watch?
Caller 2
You better believe it. I'm gonna show it off.
Leanne
I love him.
Host/Advisor
All right, Brad says bad idea. Here's TC. TC's back. What's going on, dude?
Caller 2
Hey, how's it going, people? Happy holidays, everybody.
Advisor 1
Happy holidays.
Caller 2
You know, my initial reaction was not to give him a watch, you know, just based on it just being four weeks. But they have a history together, and, you know, it is a watch, and she's had it for so long. I think she needs to take a look at how valuable her relationship with is with him, and, you know, how far that relationship is going to go before she actually makes the decision to give it to him.
Caller 1
My only fear is that she's going to give him an $800 watch, and she is going to be so disappointed in what he gets her, if he gets her anything at all. $800 is saying a lot in a relationship, is this.
Host/Advisor
I know this is going to sound superficial, and this is so not what Christmas is all about, but. But in a case like this, do you go into the gift giving session with two gifts? Cause he's not exactly sure what you're getting him either. So if he gets you something way over the top, you've got the $800 watch. But if he doesn't, you've got something else.
Advisor 2
Leave it in your purse.
Advisor 3
I did that before where I had heard that somebody was getting me a gift. A friend was getting me a gift that was way over the top because I had helped them with something, and I got them, like, a $25 outback gift certificate or something like that. And so I had to. I was like, crap, I can't go in. You know, so then I had two in.
Advisor 2
I just got a bloomin Onion.
Advertiser 2
Right.
Advisor 3
So I had to go in, and I had two of them with me.
Host/Advisor
So you had a backup gift. And what would have happened if you would have drawn. If you would have given the present first? Cause in this negotiation, that's what did happen.
Advisor 3
And I went with the cheap one.
Host/Advisor
And what did you get in return?
Advisor 3
A digital camera.
Host/Advisor
Oh.
Leanne
Oh, no.
Host/Advisor
See, in any negotiation, if you make the offer first, you lose. You lost.
Advisor 3
Yeah, well aware.
Advisor 1
But she's not going to use that watch.
Leanne
No.
Caller 1
And I don't even think he's thinking about what to get her. And if he is, it's probably going to be a Christmas card and a gift certificate to her favorite store. It's not anything expensive.
Host/Advisor
I think you got to reset. Reset on the new relationship. Hey, Serena. Good Morning. You're on Q100.
Leanne
Hey. I think she should give it to him later. If they last that long, then, you know, then. Then at that point, he would, like, I guess, deserve to get it. But, I mean, they didn't even. They didn't make it past the one year mark, so I don't think she should give him something that she was, you know, he earned over a year after they've been together for almost a month.
Host/Advisor
Agree. Way less risky if you just hold onto it until the summertime. And if he does get you something way over the top and you give him something not so over the top. Now you've got a definition of where this relationship is in his mind also.
Advisor 1
Yeah, Yeah. I just think you need to put the watch back in its storage place and save it for, like Jen said, his birthday, because I don't think you're gonna need it. And I think that's an expensive gift even for a one year relationship. But, you know, I. Yeah, I think that's way too much.
Host/Advisor
Cindy, good morning. You have some advice?
Leanne
Good morning.
Host/Advisor
Hi. So you have Leanne here, who's been dating a guy for four weeks, but she previously dated him for a year. They broke up for a year, they've been dating for four weeks, and she's got this $800 watch that she's planning on giving him. Good idea or is that a bad idea?
Leanne
I've always grown up that it was a bad idea to give a significant other a watch.
Host/Advisor
Why?
Leanne
There's an old superstition that says if you give a loved one a watch, that means time is running out.
Advisor 2
I've heard of the shoes 1. If you give a woman shoes, she'll walk out of your life.
Caller 2
What?
Leanne
Really?
Host/Advisor
Never heard of this. Yeah, there's a whole bunch of people now calling saying it's just a bad idea to give a watch, period.
Caller 1
That's funny.
Advisor 1
That is funny.
Advertiser 2
I've never.
Advisor 1
I've never heard that.
Host/Advisor
Never had any idea. Hey, Alex.
Caller 2
Hey, good morning.
Host/Advisor
What's happening?
Caller 2
Yeah. Now, do not give the watch. You don't need that complication going into the holidays.
Host/Advisor
Yeah, what kind of complication?
Caller 2
Well, you know, just the discussion that you guys are having right now, she's going to be having mentally and just leave the watch out and see whether the relationship goes.
Host/Advisor
That's pretty much the majority of the advice right there, Lian.
Leanne
All right, I guess. I guess we'll just hold on, I guess another several months. It's almost like it's burning a hole in my pocket.
Host/Advisor
Right. I can't believe you kept it this long, to be honest with you.
Advisor 1
I mean, is it a reflection of you wanting to jump right back into where you were before and you just realized that you can't?
Leanne
No, I guess it was just, you know, I held onto it because I had, you know, I specifically bought it for him. And it was just always kind of, you know, maybe I hoped we were getting back together, but I didn't want to, you know, I didn't want to sell it or get rid of it. I mean, and who's even to say I'd even get what it was worth if I sold it? So I just kind of. I just kind of kept on to it. And then when we got back together, I thought, well, you know, what's the harm in just giving it to him?
Advisor 3
What I heard was, if you give him the watch, also give him a pair of shoes so that once time runs out, he can walk back into your life.
Leanne
Whoa.
Advisor 2
That was deep, man. Deep. I think that you should get it resized for yourself and just wear it.
Host/Advisor
But what if she's still dating the dude in the summer and wants to give it to him?
Advisor 2
Then she can buy him a different watch.
Advisor 3
That's like suicide because then her time's running out. You can't give a watch as a gift. You can't get a watch from someone, nor can you buy a watch for yourself.
Advertiser 2
Those are. That's the superstition.
Host
I'm so confused.
Caller 2
All right.
Advisor 3
The only way you can successfully obtain a watch is to find one on the street.
Host/Advisor
Leanne, thank you for calling, I think, and I'm sure you're never going to do that again, but I appreciate you
Leanne
calling and thanks so much, guys.
Host/Advisor
The first show.
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Host/Advisor
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Date: May 29, 2026
Summary by Podcast Summarizer
This episode tackles a classic relationship dilemma: Is it appropriate to gift a high-value item—specifically, an $800 watch—to a boyfriend after just four weeks of rekindled dating? Leanne, a listener, calls in to share her situation and consult the Bert Show team and listeners about whether giving such a gift is meaningful or potentially inappropriate given the newness of their relationship (despite having a year-long history together). The episode evolves into a lively group debate, blending practical advice, personal anecdotes, and a touch of humor as the hosts, callers, and Leanne herself weigh in on gifting etiquette, relationship pacing, and even gift-related superstitions.
Leanne’s Background:
Central Question:
Fresh Start Advice:
Labels Matter:
From a Guy’s Perspective:
Emotional Risk:
Gift-Giving Strategy:
Anecdote:
Most callers and hosts recommend holding onto the watch for a more significant milestone, like a birthday or later stage in the relationship.
Serena: “I think she should give it to him later. If they last that long... then at that point, he would, like, I guess, deserve to get it.” ([08:43])
Host Summarizes: “Way less risky if you just hold onto it until the summertime.” ([09:04])
Summary in One Line:
The show’s advice? Don’t give the $800 watch just yet—let the relationship evolve, assign proper labels, and save the big gestures for when the commitment is mutual and clear.