I've effectively wasted $5,000 on matchmaking. I've had eight matches with women, many of them amazing women, and zero second dates. The one redeeming factor I can pull out of this is that I've learned some very clear lessons I can share with you, so I hope you don't have to learn by blowing your money the same way I have. I also have $2,500 more on the books, which is four more women I'll be matched with, and that adds up to $625 for each individual match. I'm really excited to apply what I've learned from the first $5,000 of matchmaking to the next $2,500, and I have two of those dates coming up. So I'm going to run through this as a list of things I've learned that I hope you can identify with.
I'm available if you want to talk to me. I'm actually in the middle of dating right now, which makes this very relatable if you're a man dating after divorce, or a woman dating after divorce, especially with kids. I'm doing this right now. I've been putting in a lot of effort, trying everything, and focusing on the learning.
Lesson one: putting in effort on the phone is attractive
The number one thing I've learned from matchmaking dating, and the thing that has cost me second dates, is that at least these days, a lot of people expect you to put in significant effort on the phone. I've lost at least two second dates with women from matchmaking, which you could call a $1,250 mistake. Two women were very interested in me on the first date, very excited to give me their number, sent messages, and were excited to schedule a second date with me. Neither turned into a second date, because in each case, at some point I waited two days to text them. I didn't realize how much texting is expected.
Now, not every person works like this, but I erred on the side of putting less effort in on the phone to try to look more high value. I also figured that if I put less effort in on the phone, there was less chance to screw it up with any particular text I sent. But the number one lesson I've learned is that putting in effort is generally attractive, precisely because we only have so much effort to give, and therefore there are only so many people you can really text back and forth with. While in my mind I was signaling that I'm high value and have options, in some of these women's minds they were getting the message that I'm not that interested in them, that I'm probably dating other women, which is true, and that I'm not worth their time and there's no connection.
So going forward, I'll be texting women consistently, at the rate they're texting me or higher. I'll be at least matching their effort, if not consistently putting in a little bit more and initiating the messages. I'll be the one who's willing to double text. At the same time, I'm not saying to chase every woman around. If you text two, three, four times and she doesn't reply, that's different. But persistence and effort are very attractive. I was just listening to Jack Neal, the Tinder expert, in an interview titled "Insults Get More Dates: Why Women Hate Nice Guys" with Blaine Anderson. She didn't really even say that in the actual interview, but one thing she did say is that persistence and perseverance are attractive. What's unattractive, at least in my experience with most women, is a guy who won't even put much effort into texting. Occasionally a woman will put up with it if she's really crazy about the guy, but generally not. It was an expensive lesson for me to learn, but I'm so glad I know it now, and I'm going to be texting women a whole lot.
Lesson two: be willing to reject instead of getting rejected
The second big lesson I learned is to be willing to reject the other person, to say no thanks, instead of making them reject you. On the first couple of matchmaking dates, I didn't really like either of the women right away. The first one, as soon as I saw her and she started talking, I'm like, no, no. In that case, I should have ended the date much earlier, and not tried to lead her on and plan a second date and then put her in a position to reject me. I should have just said, look, I'm not feeling this. But in my mind, the default is often to try and make the best of whatever I've got in front of me. And there seems to be some kind of attraction in me to being the one who gets turned down, because it feels easier than being the one who says no.
I just went out on a date with a woman I met through a mixer, and I rejected her pretty hard on the date. I did a video about this before: what she said about disciplining children was absolutely awful in my mind, and I told her that. I said, that's a major red flag for me, that's not compatible with me at all. I very clearly told her, this is the red flag, this is the reason, and this is not going to work with me, so at least she can learn for the future. But with the first couple of women from matchmaking, instead of cutting the date off as soon as possible, which is what I've learned to do since my time is valuable, I kept going. With both of those women I knew right away I wasn't attracted to them, and when they started talking, it got worse. The self-respecting thing to do would have been to end the date as soon as possible, at 30 minutes or an hour, and say: thank you for your time, I know this isn't the right connection for me, if you want more detailed feedback I'll provide it, but let's wrap this up and I'm going to head out. Thank you for meeting me tonight. That would have been the most honest thing to do.
Instead, I just kept talking enough that it was like I was intentionally throwing out red flags to get them to say they weren't feeling it. And from there, I ended up feeling like, oh, no woman wants me, because these women I didn't even want were saying they didn't want me. It makes it harder to keep your own self-confidence when you're acting like that. Two women ago, on the other hand, I felt sad. I felt empathy for her, because she seemed to really like me. She was giving me a lot of high-interest signs, like making hours available to go out on our first date, and she was super excited.
Lesson three: never think you're not good enough for her
On my third match, I could see her doing what I had been doing. My third match from the matchmaking service was finally a woman who was very attractive, very professionally successful, and fun, and she was more than a decade younger than me. I was like, oh my God, this is so amazing, I'm out with her. And I slipped into being insecure and trying to brag, feeling like I wasn't good enough for her. That's a really bad look, because I am good enough for any woman. There's no woman who's out of my league. In my own mind, I'm a top-tier man for what I have to offer. If you want to date the richest, most powerful guy, then at least right now that's not going to work with me, but I know what I have to offer, and I'm very proud of it. There's no woman I'm going to go out with where I'm going to think, well, I'm not good enough for her.
So there's no reason for you to ever have a story in your head that you're not good enough for somebody else. Often, when you feel like you're not good enough, you'll start trying to compensate, and ironically, the compensation is really unattractive. It proves the exact thing you're trying not to prove.
For example, the woman I went out with who talked about disciplining kids: I could tell she was trying really hard to compensate with me, which is funny, because in my mind she was really attractive. She's very active and fit, she's got a good business, and from my point of view she was definitely good enough. I don't see why she was compensating so badly, but she was bragging a whole lot, talking a bunch of junk, and putting other people down. You could see she was coming from a place of being overly excited to be out with me. She didn't feel good enough, so she tried to compensate, and her compensation put me off a lot. I ended up leaving feeling like, this is not right at all, I've got to get out of here. At the end of the date she said, well, I guess I'll be okay if I'm by myself for the rest of my life. I told her I didn't think that's what was going to happen. And she said, well, we need to give people a chance, a second and a third date, to really get to know them. I'd been saying the same thing to some of these women before, but I realized that with certain levels of behavior, no, you're not going to get another chance.
And the way I acted on my third match, I'm not getting another chance either. I showed up trying to brag that I've gotten a billion views online, and then when she talked about her career, I had to bring in my family and their careers to feel like it was appropriate that we were out together. At the end of the date, I was really weak asking for her phone number, not confident at all. I was simping so badly. Then I radically overcompensated on the fourth date and went overboard with "I'm good enough," and I was too avoidant. That's how I ended up not texting that woman after the fourth date.
The fifth match: she said I wasn't physically attractive
On the fifth match, I at least did reject the woman. She said she didn't find me physically attractive after we had already scheduled a second date, so I canceled the second date on her. I'm like, that's not going to work. If you're saying that right now, I don't know if you're just saying it or if you really mean it, but I'm not dealing with that. So on the fifth one, I did stand up and say, look, that's not going to work for me. You go out with some other guys you do find attractive, and I'm going to be with a woman who does find me attractive, because I am a good-looking guy, and there are women who are really excited to be out with me. Sometimes you just shouldn't expect every date to work out.
Lesson four: schedule active dates
That date also helped me see that she didn't have a chance to see I was physically attractive, because we had a sit-down dinner date. Compare that to the queen. When I went out with her, we did a hot yoga class together. I've got my shirt off, I'm sweating, I'm enduring all these poses, and I'm outlasting the other guys in the room except for one dude who's super ripped and in crazy shape. The other dudes and some of the women are having to quit. I'm showing that I'm strong and physically attractive. That helped me see that I need to have active dates whenever possible, to help a woman see me move. It's going to be hard to show a woman anything besides basically my face if we're just sitting down at a dinner. So I've learned to schedule a lot more active dates: coffee dates, tennis dates, dates where we can move and walk. You can see how my body moves and how I walk, how very healthy I am, versus just sitting at a table where it's hard to see that someone is that physically attractive and lean. You just don't have that much time.
Lesson five: a date should be fun, and dress for it
On the sixth match, I went out with a woman and it was like my clothes didn't match my personality. I was just kind of boring. I was in interview mode, and a date first and foremost should be fun. I realized that one of the main things women are looking for on a date is flirtation and fun. You can always ask some interview questions, but I was treating that sixth match like a job interview, asking where do you work and all that crap. It was boring, and my clothes were boring. I had a blue Under Armour polo on with some shorts and tennis shoes, and I could tell she was dressed up nicer than that, even for a 9am coffee date.
I realized I do have nicer, more formal dinner clothes. I spent about a thousand dollars when people were telling me my clothes sucked, and I got some really nice clothes that are great. I wear those shirts for recording my videos a lot of the time, and they're great for going out to dinner or somewhere you dress up a bit more. Some of the women I went to dinner with were certainly satisfied with my clothes, at least. One of them found me attractive right up until I stopped texting her. But those clothes are too over the top for a coffee date. They look like you're trying too hard. You still need to look good, though. So I went out yesterday and spent $500 to get a nice short-sleeve shirt that also looks beautiful, plus some chino shorts that don't even hit my knees, so you can see I've got the kind of legs that gay guys will hit on me for in the grocery store. I've got some serious calf muscles from playing tennis and running. I'm in shape, I'm lean, and my legs are very strong, and now I've got shorts that show that off. I've got shirts that look beautiful and colorful and match my personality, which is colorful. I'm not a boring corporate guy. I'm a pretty colorful content creator. And I got some nice, fresh, brand new shoes that go with the outfits.
Especially if you're on a matchmaking service, these women expect that you had enough money to pay for it. I showed up to the eighth match in a plain t-shirt, because I felt like I'd been trying too hard and hadn't had a great coffee date, so I just put in no effort at all. Between that and not texting her, she did like the actual experience of being on the date with me, but it's very easy: somebody doesn't text you for a couple of days, then you reflect back and think, well, he didn't dress up, this guy's just not putting in any effort. Especially on a matchmaking service, these women are expecting effort. They're expecting you to show up and look nice. On the plus side, I've got a watch I've worn on all the dates that looks good.
The seventh match I threw away
Then there was the seventh match. I had committed to the queen, so I canceled the seventh match and basically blew a $625 match, which was a total waste. I wouldn't do that again.
Why I don't regret the $5,000
So I'm grateful. In some ways you could say I just threw this $5,000 out the window with zero second dates, but I'm learning rapidly, and I'm teaching this. If you can interpret everything as learning, getting better at the game, understanding how things work, and setting yourself up to help other people, then you can see this as $5,000 I invested in learning how to date. Now I've got a dating channel that's monetized. I've got dating coaching available, and I have calls. I'm in the middle of dating right now. I've gone out with around 25 women this year, a new woman every week or two, and I'm about to get back on dating apps, which is going to speed that up even more. Most of this year I haven't even used dating apps. These have been women from matchmaking, meeting women in person, cold approach, referrals through friends, and a handful from dating apps too.
To me, we spend a lot of money on things like education, and investing $5,000 to get dates with eight different women and learn lessons from each of those dates has been very valuable. Now I've got two more matchmaking dates coming up within the next week. I've got my clothes on point. And I also know that no matter who the woman is, no matter how hot she is, how smart she is, how much money she might appear to have, or how much fun she is, I should never think I'm not good enough for her. I'm good enough for the woman, no matter who she is. And the more I desire her, the more I might be a great match for her. Women generally like to be desired. They want to be with a man who desires them, not some guy who's like, yeah, I guess you're all right. That's what my ex-wife loved: how much I desired her. I was nuts for her, and she loved that. My friend, who's been on this planet a long time, said one of the top things that makes a woman like you is that she can feel how much you desire her, while at the same time you feel like you're an appropriate match for each other. Not "I desire you and I'm not good enough," but "I'm good enough for you, I really like you, and I desire you a lot."
Matchmaking is dating on hard mode
So the matchmaking money I've spent, I would not take back if I could. It's been really valuable. What I've learned in matchmaking has helped me with women in person, and it's setting me up to do better on dating apps too. I'm grateful I still have four more matches left. In all my other methods of dating this year, I've only met one woman who was on par with the matches I've consistently gotten from matchmaking. Matchmaking is like playing dating on the harder difficulty. Many of these women I wouldn't have been able to get on a date through dating apps, or I would have had to do a lot of cold approach and go a lot of places to meet these kinds of quality women. It's felt like I've been playing on hard mode. Somebody said, oh, none of these matches are ever going to work out. I'm like, that's not true. I know what I have to offer, and I'm putting in the effort. Every one of these lessons is going into my Dating playlist as I go.
That is enough for this one. If you want to talk to me, go to jerrybanfield.com. Thanks for reading.