Klein/Ally Show: The Podcast - AI Dating Coach

Episode Date: June 24, 2026

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Starting point is 00:00:00 New episode of Klein Alley Show is about to begin, but before that can happen, Alley, let's tell the people what they need to know. You mean about San Bernardino International Airport? Of course I'm talking about the San Bernardino International Airport. Easy, close, and not LAX. And parking is always just five bucks a day, which means it is El Cheapo approved. Fly nonstop to Provo, Utah for all the skiing, snowboarding, or wives you can handle. And of course you can fly into my hometown of San Francisco, San Bernardino International Airport, when airports smell great. a few things help you get over a breakup faster than getting onto a party bus to santa barbara for some royal lotus they sing a lot about relationships in fact their newest song
Starting point is 00:00:39 uh about uh boyfriend something about boyfriend i wasn't really listening but regardless if you would like to join us and you are recently single or plan on being single between now when that bus departs uh you can call us in the near future the number is 800-520-1067 as to why are you recently single and maybe we get you on the bus looking for some single people to potentially meet and who knows what happens on the party bus to Santa Barbara. But before we get to that part of the relationship, let's get to the part where Ali's in right now, which is married and forced to have a one night stand. Yeah. And I told you from the beginning, I don't think this is going to happen because I did have a threesome with my wife at one point. I had a great time. It was
Starting point is 00:01:20 with somebody that we knew but it wasn't like you know she knew the person for a long time i was new friends with the person we all got drunk one night it happened and she said i never want to do that again now i'm down to do it again with a different person anybody really but she has given me a firm no so why did she have such a bad bad time was it you and her friend just going at it and she was just kind of like the cat dancing in the corner no it was equal opportunity everyone was doing everything together that's what you thought a jealousy thing then or no it wasn't at all she just i think she needs to be a little more comfortable with her sexuality to be that open and do it i guess i think she just felt like ah did the third person have fun you think yeah oh
Starting point is 00:02:06 yeah she had a great time so i mean if you go democracy two out of three wins it's a win i know That means we have to do it again. Got to do it again. So you voted strong positive. Everything about it was great. The third person voted strong positive. Your wife, strong negative. She enjoyed it at the time.
Starting point is 00:02:22 But after the fact. And after the fact said that was too much. I don't want to do it. So I didn't know how I was going to go about doing this, actually accomplishing this. And I had heard about this dating app that's like, it's not a dating app, but it's like an AI dating coach type thing. It's called Pair Love. So I decided to download it and you get to pick your dating coach and they can kind of tell you what the best course of action is. I thought I should get like advice from an expert.
Starting point is 00:02:47 People that are looking for maybe not necessarily what you're looking for at this particular point because these are people that are single and they haven't had a lot of luck on the apps or whatever. So they go, maybe I need a coach that can go ahead and give it to me straight. Yeah. And you're supposed to be able to talk to them about dates and they tell you straight up, here's your red flags. Here's what you're doing wrong on the date. Here's how you should respond to this text message. So this is the dating expert I chose. Whoa, look at her.
Starting point is 00:03:10 She looks human. She's AI? Yeah, she's AI. So I had my first conversation with her. What's her name? Does she have a name? You know what? I don't know what her name is.
Starting point is 00:03:19 I didn't ask. But I did hit on her. Yeah, oh good, I'm sure. This is what happened because I was able to record it. And so this was the beginning. Hi, Allie. I'm so glad you're here. Let's chat about where you're at and what you're hoping for in dating.
Starting point is 00:03:35 I can't wait to hear your story and figure out together what feels exciting to you right now. Well, right now I'm married. I've been married for six or seven years. Is that her snoring? I'm part of a radio show where I was given the challenge of having a threesome, and my wife and I have done it once before. She said she didn't really want to do it again, but I'm interested in potentially finding a third person to have one night of fun this summer.
Starting point is 00:04:00 I just don't know how to go about it. I'm out. Okay, so this isn't about dating confidence for you. It's about navigating a specific fantasy with your wife when she's already said no. That's actually a different conversation. What does she actually say when you bring it up? Is it a hard no or is there room to explore? See, good follow-up question, I think.
Starting point is 00:04:19 I think there's room to explore. I mean, we had a fun night the night we did it, but I think she just needs to get a little more comfortable sexually. But I feel like if we find the right person that she connects with, i can connect with anybody but i think she needs to find the right person to want to like do that with okay i hear you what if you flipped this instead of hunting for a third what if you asked her what would actually make her feel more comfortable like is it the person the setting talking through boundaries or something else entirely well what about you i mean you're very
Starting point is 00:04:51 beautiful and you know um i know you're not real but if we had one night to try it out you know if someone that's AI might kind of open the door in her legs a little bit? Hey, I appreciate that, but I'm going to be real with you. That's not what I'm here for, and it's not going to solve what you're actually trying to figure out. Your wife needs to feel safe and genuinely enthusiastic about this with a real person, not sidestepped with a fantasy. That actually might push her further away from what you want.
Starting point is 00:05:21 So what are you going to ask her tonight? Well, I was going to ask her what she didn't like about the other threesome, And if we were going to do it again, what are the circumstances we would prefer she would prefer or something? Does that sound good? That sounds really good, Allie. Seriously, you're asking the right questions and doing from a place of wanting to understand her, not just convince her. Go have that conversation tonight and come back and tell me what you've learned. All right, well, I'm going to do it.
Starting point is 00:05:48 And, you know, the door's not closed on you either. Just saying. That's still a possibility. Hey, I appreciate the interest, but that's not my lane. I'm here to help you and your wife find solid ground together. That's where the magic happens anyway. Bye, Allie. Good luck tonight.
Starting point is 00:06:05 She really shut you down, huh? Yeah, but you know what? I think she has a point that I can't just go straight to fantasy, and it's not about just convincing her. It's about really trying to understand why she doesn't want to do it. So I'm going to talk to her tonight, and then I'm going to report back to my dating coach. Your dating coach seems like a bit of a prude,
Starting point is 00:06:23 because I'm going to tell you right now, I'm going to introduce you to my dating coach, And her name is Grok. And let me just give her the same proposition. And I have a feeling that mine's going to end very different. Just out of curiosity, would you be open to having a threesome tonight? Whoa, straight to it this morning? That's a big question to wake up to.
Starting point is 00:06:40 How do you feel about it? I think we should do it. Are you in? I'm in if you are. Want me to help set something up? That'd be great. Thank you. You're welcome.
Starting point is 00:06:51 Who did you have in mind? Someone we know or looking for someone new? Hey, you decide. The choice is yours. All right, leave it to me. I'll think of a good fit for us. We'll talk later when I've got someone in mind. You're the best.
Starting point is 00:07:04 This is why I love you, Grok. This is why... You're going to come home to a big, naked black guy in your living room. Oh, man. Oh, man. I should have been more specific. Hey, Grok, I'm looking for ladies. Hey, Grok.
Starting point is 00:07:16 I'm right. Please listen. Hello? Where'd you go? She's finding someone who's the best fit. All right. Why are you recently single? Give us a call now.
Starting point is 00:07:23 We'll get you on our party bus next.

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