Two Women, One Day
I'm Jerry Banfield, and this is my vlog for October. October, bro? What month are you in? August 29th, 2026. What an awesome day today. I have two women that I'm somehow trying to schedule dates with, both of them tomorrow. I don't think it's going to work out, but I literally just met both of them today. I went to a speed dating event today, and I went to a singles mixer event, and I got a phone number at both of them. Let me tell you the story. This is cool because dating has been the most interesting, the most emotional, most challenging, and most fun part of my life this year after getting divorced last year.
My video yesterday was talking about the drama with the yoga studio because of me being single and asking other women there if they were single. Today I did some yoga in my house, just like five minutes to stretch, and then I went for a run. I'm like, this is great. This is what I need to be doing. I don't need to be taking an hour and a half or two hours to go do yoga at a studio somewhere. I can take ten minutes in my house to do some yoga, stretch, go run, and it's all good.
An Open-Hearted Morning
So today I woke up after we had such a beautiful party for my daughter last night. It was really nice for her birthday. My mom came over, and my ex made a cake for Madeline to bring over. My son was there. We had such a beautiful birthday party, and I just felt so open hearted. I'm like, man, I see what I did with that last woman. I need to be open hearted. Great. Very good. So the kids got up, and we were off to my son's baseball practice. I got him all set up in his baseball uniform. It was so cute. Then I went to my AA meeting and had a really nice, open hearted AA meeting. Some of the meetings lately have been like people wanting to fight me, but this one wasn't like that.
I noticed that what I do sometimes impacts how I'm showing up in the rest of the world. Most of the time in the real world, being loving and cooperative and supportive is what gets the best results. But on YouTube — and I filmed a video about this today on my Jerry Banfield Creators channel — often what gets the best results is being hostile, confrontational, talking a bunch of stuff, putting people down. That's often what actually gets a lot of views on YouTube. And I noticed in my dating life there's kind of this conflict, where there's an incentive to keep having an interesting, dramatic dating life, because that makes for better content than having a woman I'm really happy with. Then there's kind of not anything interesting to talk about. It's like, yeah, we had an awesome day today, and everybody's like, next — where's the drama?
Finding the Speed Dating Event
I was sitting at home after the AA meeting. I talked to one of my friends from AA for like an hour, and I knocked out several videos for the channel. And then somehow I thought of speed dating today. Before, I was never doing that again. The last speed dating event, I just felt like it was poorly organized. It was a total waste of time, and I'm like, never doing that again. But today I'm like, what? I don't have anything else scheduled the rest of the day. Let me just look. I got Facebook now again, which I didn't have before. So I went and joined this St. Pete Facebook group, and I scrolled down, and I found this event in Sarasota. Then I found a speed dating event. I wasn't looking for speed dating — I was like, I'm not going to do that. I was just looking. I saw the speed dating event and I'm like, let me look at this. I looked at it, and I noticed they'd sold more women's tickets than men's. I'm like, all right, let me try this. Let me just give this a shot. So I signed up for it.
It was in Tampa. I drove over there, and this speed dating event was really well organized. They have an app that you scan, and when you scan the app, you're connected — you're matched on the app. So you can both message each other, and you don't have to exchange phone numbers. Super easy. I joined the app. They've got a membership, and then you can go to all the speed dating events — it's like 70 or 80 bucks a year or something.
My mindset with the speed dating was, this is going to be good practice. I've got a matchmaking date a week from now, and for a matchmaking date, I want to be on top of my game. I want to be ready to show up open, heartfelt, having fun, flirting. I want to be able to offer the best version of me to a woman that's on a high income matchmaking service. If you want to try that, those have been some of the best dates I've been on all year — very high quality women on there, and I'd like to think very high quality men on there. Like me. I went to the speed dating event thinking there's not going to be any hot girls there, there's no point in even going. But like, bro, just practice. Doesn't matter what they look like. Practice talking to them. Practice flirting. If you can talk to a woman you're not attracted to and flirt with her, you can certainly do it with one that you are attracted to and you're really compatible with.
Walking In
So I go there, and this coffee shop is stuffed. I parked in Tampa somewhere in grass that was like two feet high. I was going to park in this one spot, and there was a homeless dude sitting on the corner right there where I had to pull in — his feet were right where the car was going to park. So I'm like, ah, and I parked in this tall grass instead. I walked in wearing a black shirt and white pants — a shirt that cost like a hundred dollars from State and Liberty at International Mall in Tampa.
I walk in, and I'm like, all right, there are a few pretty women here. Nice. And I've got to say this, because it's true — I was thinking it. I saw there were so many big girls. As I drove up and started to get close to the coffee shop, I just saw groups of big girls, and I'm like, it's got to be the speed dating event right now. They're all here for that. They've got a captive audience. And if you love big girls, please — y'all do love those big girls, all right? I like lean women. I'm a lean guy. I like lean women. I love my lean women. And I walk in, and there are some lean women there too. I'm like, nice. And I'm thinking I might be one of the best looking dudes there, if I do say so myself. But there were some other good looking dudes there — all kinds of flavors of dudes. Tall dudes, short dudes, black dudes, white dudes, Indian dudes, Mexican dudes, all kinds of dudes. I'm like, this is nice, that women get to roll through a whole bunch of different kinds of guys, and hopefully somebody goes home happy.
So I sat down, talked to the first woman, rolled through, and talked to the next 20. And man, I do these videos and I can talk for six hours straight, but going back and forth with like 20 different women in a row is tiring. As soon as it was over, I just headed out. I'm like, I'm going to message these women on the app — I need to get some peace and quiet and some time by myself.
Finding the Mixer and Messaging Eight Women
At the same time, when I found that speed dating event, I started looking at other events, and I found this mixer event in Sarasota, where I used to live. It's a mixer event where you get wristbands — green wristbands if you're single, yellow if you're like casual, red if you're in a relationship. I'm like, great, I've been trying to go to something like this, where you know who to talk to. It was at a bar, but I'm like, it's fine. I'm not trying to drink. I've been sober 12 years. But I got home after the speed dating event and I'm like, I don't have time for this right now. I don't have time for this. I'm good. I already went speed dating.
And dude, this vlog is going to continue to get better, all right? We're just warming up. So I go on this app, bro. One, two, three, four, five, six, seven, eight — I messaged eight women on this app out of, I guess it was 16. I didn't message the others. One was just kind of weird, but the rest were all lovely people. I'm like, God, if you were 50 pounds smaller, I'd definitely be messaging you, but I hope someone finds them and loves them. This one girl really had a pretty picture too, but I'm like, ah, sorry. So I messaged eight of them, and literally the message said: hey, name — I enjoyed meeting you tonight. I'm available to plan a date when you're free. I was like, all right, I'm going to just message all the women that I had any attraction to, and we'll see who messages back. That was all I was filtering on: are you attractive or not?
My Texting Screwed Up
Nobody said anything crazy enough where it's like, okay, whoa. Actually, one woman probably did, but I messaged her anyway. So I was trying to go through and copy these messages — the message that said I enjoyed meeting you tonight and I'm available to plan a date when you're free. I tried to copy that, but somehow the first message got misspelled. So I copied the second message, which for some reason I copied the girl's name with. And then for girl number three, I sent a message that said, hey, one name. Hey, another name. And then the next message I sent was: oh my God, LOL, my texting screwed up. So embarrassing. Laughing face. No response from her. I was like, bro, come on now. Why are you texting like that?
Then this one single mom messages me back. Her kids are teens, older than mine. She messages me back within like 30 minutes. She says, hey, I enjoyed meeting you too. I would definitely like to see you again. I'm like, all right, you're not playing. And then I'm like, wait, was she attractive in person? Hold up. I'm looking at her picture. I'm like, all right, I definitely remember. She was cute. She's got a real pretty face. And I'm like, bro, come on now, I hope I didn't message the wrong one. But I'm like, yeah, I remember talking to her. I remember what she said. I remember where she was sitting. I have a very position-based memory, which works great in games like Call of Duty Warzone. I remember exactly where I was sitting, where she was sitting. And I'm like, yeah, she was definitely pretty. I liked her, and she was fun. We had some laughs. I'll sit down trying to make all these women laugh — I don't care what they look like or anything. I'm trying to flirt, I'm trying to make them laugh. So she messaged me, I gave her my phone number and said, let's do something tomorrow.
Deciding to Go to the Mixer
So I'm at home. I've got some white mushrooms and I throw them in a pan with some leftovers from my son's lunch — some carrots and broccoli that were in his lunch. I put the coconut oil in with it. I take the coconut oil from next to my bed and put a scoop in there. I'm like, damn, this stuff is really useful. There are so many different things you can use it for. So I cooked it up in the coconut oil, and I'm thinking about this mixer in Sarasota. It's a 45 minute to an hour drive, and it's raining like hell outside. I'm like, man, I'm done. I've socialized enough. I don't need to go to this mixer. I just want to stay home. One of the guys in the Jerry Banfield Skool community said, hey, we missed your gaming streams — come do a gaming stream. I'm like, let me just stay home and do a gaming stream. This mixer's at a bar anyway. I don't need to go to a bar. I'm sober.
And then I started to think: what would be fun? What would be fun tonight? I'm like, damn, I've got to check that mixer out. That would be fun. It would be fun to drive to Sarasota and go to this mixer at a random place I've never been to. And I was like, but I could stay home. I could play video games. I could do content. I could go see my mom. I'm like, bro, you're single. Go out. Go have fun. Go on an adventure. So I'm like, all right — fun, locked in, fun.
And then I'm like, man, I don't have an outfit to be going out in. So I asked ChatGPT, should I wear this Under Armour shirt? And it's like, no, that Under Armour shirt's weak. I'm like, well, what should I wear then? I took a picture of my other shirt, and it's like, wear that shirt. That's your best going out shirt. You need to buy a better movie star looking shirt for you and your silly YouTube personality, but this will work tonight — wear it with your nice gray slacks. This is a $200 outfit from State and Liberty. I should be getting paid for saying that, but I'm not. And I've got my watch on, my black casual shoes, black belt. I look good. So I'm like, all right, let's go to Sarasota.
Rolling Up to a Bar, Sober and Solo
I get in the car. Once I make the decision, I'm like, I'm rolling, baby. Let's go. I got dinner down. I'm going to be a little bit late — that's fine, it goes from like 7:30 to 11. So I head out a little after seven. I'm driving down, I call my mom on the way, talking to her, having a great conversation. I roll up, and for parking you've got to go around and park by Best Buy, and there's construction. Took me like five or ten minutes to park. And I get out there, and I haven't been to a bar or a social event like this in a long time. I'm sober. I'm by myself. So I'm like, all right, let's see how this is.
They had an attendance list on their web page of 100-some people who said they were going, and the event was only $30. So I copied and pasted all the names and just dumped them into ChatGPT, and I'm like, is this going to be a sausage fest? And ChatGPT is like, well, based on the names, you've got mostly men, then some undetermined names, and then you've got women. It said, I'd probably say it's going to be 70-30, maybe 60-40, but it depends on who people bring. So I'm like, all right, that'll be fine.
I walk up, I get my wristband — I got the green wristband on, single — and I'm awkward as anything. I'm standing around. I don't know what to do. It's crowded — the entrance is crowded. So I'm standing around like a tool. I walk over next to the bathroom and wait in line. Meanwhile, it's 11 p.m. now as I record this and I still haven't been to the bathroom in four or five hours. Four hours. Final answer. And I'm standing there like, dude, what are you doing? You don't need to go to the bathroom. You just went 50 minutes ago. Come on. So then I go outside, and I end up standing out of habit by the bar. I'm like, I'll just get a mocktail or something. The bar is going slow as hell. And I'm like, I don't know what to do. I'm remembering all these dudes like Owen Cook — yeah, get up there and say hi to all these dudes and make a scene. I'm like, I don't feel like doing that either.
Standing by the Palm Tree, Scoping the Scene
So I go stand over by this palm tree in the ground — I don't know if it's a palm tree, but it's got like three things coming out of it, and it's in gravel. It's a perfect spot to stand because everybody's not trying to walk by. There's a chair there, and I stand with my arm on this chair and look like a complete tool for at least 20 minutes. I don't try to talk to anybody. And it is a sausage fest. I'm like, shoot, there are like two or three decent looking women here, and dudes are just taking shots one after another. Then there's this one woman who gave me some crazy vibes, and she's going up and approaching dudes herself. I'm like, nice. I'm going to just stand here — maybe she'll approach me. She did not. I'm like, why did she approach this dude with the beard? Then he approached these other two women. I'm just watching. I'm people watching. I'm stimulated just by that.
I'm not trying to talk to anybody, but I'm scoping out the scene. I'm like, who's going to be my person to talk to? All I care about is identifying the one person that I really want to talk to. I don't care about any of these other conversations. All I want is to laser in on the one person that I'm going to vibe with. So I'm just standing there looking, watching, paying attention. Then one of the hottest women there, with a green band on, walks right past me. Some other dude's talking to her. She gets tired of it, walks off, and leaves him behind, and she's on the dance floor by herself. I'm checking her out. I'm like, all right. She's got some cool earrings on. Beautiful, lean. I'm like, all right, this is good.
So I'm just standing there again, looking like a tool with my arm on a chair. All I'm doing is looking. One guy walks by me and he's like, nice shirt, bro. You look like you're from the IT department. I'm like, thanks, I guess. This is the best stuff I have to work with right now. I'm going to get some movie star looking shirts. I'm going to go to the thrift store and buy something — something that looks more accurate to what a character I am.
And then the woman who walked by before, who went to the dance floor, comes and sits right in front of me. There's a whole table full of people, and they all got up and left, so there's an empty table like a foot in front of me. All four chairs are open, and she sits with her back to me, in the chair right in front of me. I'm like, she wanted — I could tell she wanted me to push up on it. Before she knows it, I'm all on it. I'm like, this must be the one right here. But I'm not jumping on it right away. I'm just standing there playing it cool. She didn't say hi to me or anything. I'm like, whatever. Five minutes later I'm still standing there looking like a tool, and I'm just about to leave. I'm like, what? This place is mostly dudes. There are a few hot girls here, but... and then this happened.
Getting Invited to the Table
This woman who had walked up to the table earlier and started talking — one I don't find attractive at all — sees that I'm standing there looking like a tool and I haven't talked to anybody. She's like, hey, why don't you come over here and talk to us? And it's right next to the woman sitting in front of me. I'm like, all right, cool. So I walk over and I shake everybody's hand at the whole table. I'm Jerry. They're like, what? Because the music is loud. I'm like, Jerry — like Seinfeld. And as I'm shaking hands, one girl's like, you've got a nice handshake. I'm like, hell yeah, I'll be pumping that thing.
So I start talking to the two women — the one to my right and the one to my left are both talking. As soon as that conversation dies down, I start bantering. I start touching the woman next to me gently on the arm. I'm being flirty. And then finally, the one that invited me over to the table stops talking, so I start paying attention to the woman to the right — the one who sat down in front of me. I can tell she wants me to push up on it. So I slide over and sit down next to her on the other side. And she's cool. She's talking mad stuff, she's swearing, she's making gestures. I'm laughing. I'm like, she's funny as anything. We get to talking, and I end up with my arm around her chair. I put my hand on her back and leave it there. We're playing, we're having fun, we're laughing, we're talking all kinds of stuff. I'm flirting. I'm asking questions. She's asking questions about me, and I'm trying to switch it back over to her as soon as I can. She's having a good time. I'm like, damn, all right — this was worth it. We both talk about our divorces and stuff, and we have a great conversation for an hour. The first 20 or 25 minutes I was there dragged. That hour flew by talking to her.
Two Sober People at a Bar
I see her drink is empty. I'm like, you look like you need another drink. She's like, I'm just drinking water. I'm like, nice. I'm sober — 12 years — even though we're both at this bar, neither of us is drinking. She's like, yeah, I've got to drive home. I'm like, me too. I'm going back to St. Pete — this is a 50 minute drive for me. So a little later I'm like, hey, you want to get out of here or something? She's like, no — she wasn't quite ready. But I'm like, hey, at least I offered. So she kept talking with me. Then a couple of other people distracted her — some dog came over, and she loves dogs — but she came right back to talking to me after that. And I kept my arm around her chair, letting these other dudes know: hey, I'm working on this right now. And also just to be close with her, because the music was loud and we had to talk in each other's ears.
Then I can see she's ready to go. I'm like, it looks like you probably need to get home and get to bed, don't you? She's like, yeah. So she's like, I've got to hit the restroom. And my silly self is like, all right, I'll just wait here for you. She goes over to the restroom, and I'm like, why did I say that? There was a line for the restroom — I should have just walked over with her. But at the same time, I'm like, why not? Make her come back here, and we'll see if she's interested. So now I'm standing around like a tool again. I get up, I'm dancing a little bit — the DJ's finally playing some decent stuff. And then she comes back from the bathroom like ten minutes later. I'm like, all right, I'm definitely getting a phone number here. Maybe we can make out or something. And she's like, you're going to walk me back to my car. I'm like, hell yes, I am. So I walk her back to her car. I'm ready to go for a kiss, but she's just ready for a hug. So I'm like, cool. She gives me her business card. I get in my car, and I text her like two minutes later. No games, no nonsense. I'm texting her immediately.
Texting Her Like She's the Queen
And this story continues — we're not even done yet. I've got four texts from her right now. So I texted her: hey — her name — this is Jerry Banfield. Thanks for making tonight fun. She's like, so great meeting you. And this is nice: like with the queen, I texted her flirty and fun. With the last woman I went out with, my heart was so closed up that I couldn't text her like that. With this woman, I'm like, we're not doing any of that. Text her like she's the queen. So at 9:54 p.m. I sent her a message, and she replies at 9:56, while I'm trying to get in the car and drive home. She says, so great meeting you. And for a moment, I'm like, I don't know what to say next. Nonsense — you do know what to say next. So I said, yes, when am I seeing you again? LOL. She's like, when are you free or available? I have to check my schedule too. I said, tonight, LOL — but I think it's past your bedtime. She said, truth, LOL.
So I'm like, how about something tomorrow in the afternoon? She's like, perhaps — where would you like to meet? I said, why don't you come up to St. Pete? She's like, that'd be awesome, but I can't because of her work. So I'm like, all right, I'll drive down and meet you somewhere near where you're at. Then she sends three text messages and offers tea, coffee, a lunch or dinner date — all of it. And I said, let's meet for coffee or tea. She's like, cool. Then I sent her three messages when I got home. And she just gave me a place to meet at three — but my silly self forgot I have a massage scheduled tomorrow at 3:30. I'm like, shoot, I can't be in Sarasota tomorrow at 3:30, man. So I'm going to need to reschedule this date with this woman.
Something's Got to Give Tomorrow
So now I'm trying to schedule two dates tomorrow, and I have a massage, seeing my kids, and going to an AA meeting. I'm like, something's not going to work out. It's fine.
And dude, at the speed dating there was this one guy I sat down and talked to. I love talking to dudes at speed dating, because you're in the same boat there. I had a great talk with him, and he ended up subscribing to both my vlogs and my Jerry Banfield dating channel. It was great meeting him. What a day: five minutes of yoga at home instead of studio drama, a beautiful birthday party glow, an open-hearted AA meeting, 20 speed dates in Tampa, and a singles mixer in Sarasota that turned an awkward hour by a palm tree into the best conversation of my night. If you want to follow how these two dates — and the matchmaking date next week — actually turn out, the whole day-by-day story lives in my Daily Vlogs playlist. I've been talking for 27 minutes — holy smokes. That's where I'll leave today's story.