Old Man Dating by David Wygant

Recently I was hanging out with the boys (Yakub and Khiem) and we were talking a little bit about me being one of the “older guys” in this dating community – not that I’m that ancient, folks – I can still kick anybody’s ass in their twenties. I’m in better shape than I was 20 years ago, and I don’t look my age at all.

But – I’ve got the wisdom and I’ve got life on my side and I really enjoy being in my forties. It’s such a peaceful time. I remember my twenties really well, and that is why I really love hanging out with and coaching guys in their twenties – I can really relate to them.

I can relate to the pain, and the drama, and all the insecure moments – the voices that never stop in your head, and the drunken monkey that doesn’t allow you to talk to a woman because you’re feeling funky or whatever it might be.

I remember learning about the street pickup – I remember seeing the movie The Pickup Artist when I was in my twenties – Robert Downey Jr. was the pickup artist – you should rent it, it’s a lot of fun. I think Molly Ringwald was in it too.

Molly Ringwald was always kind of funky at best – I was never really THAT attracted to her, but in kind of a strange way, sometimes I was. She’s one of those women that you look at and say she’s like ugly-cute – somebody you just can’t believe that you’re attracted to, but you just have the hots for her.

But anyway, I remember walking the streets of Manhattan all of the time, seeing girls (and back then they were girls – they weren’t women) and wondering what to say, and I remember stopping at the stoplights sometimes, and some days, I’d be able to look at them at a stoplight and say, “race you to the next corner!” or come up with something clever and fun that would engage them in conversation.

Other times, I would get to the stoplight, I’d look at them, they’d look at me, and I would stare at them. They’d walk away, and I’d still be staring at the spot they were standing in a minute later. This was days before the existence of any sort of pickup community or dating gurus. There were no audio programs – this was all hit or miss.

I had to learn all of this stuff on my own. I had to go out there and do it on my own – there was no coach to pay money to and hang out with for a weekend to teach me all of the tricks of the trade. I had to go out there and learn all of this stuff – and it was torture.

I would beat myself up – if I saw a girl that I liked and then I didn’t go and talk to her then, and then ten minutes later I would think of the right thing to say to her, I’d think about that all day long.

Sometimes I would walk that same street the very next day hoping to run into her again – god, when am I going to run into Blondie from 80th and Amsterdam again? Or when am I going to run into 72nd and Columbus girl again? Or the 66th and Broadway girl?

I spent so much time obsessing about missed opportunities. And there were a ton of them. I didn’t have the social skills developed at that point. Granted – I was a good-looking guy in my twenties, and I was gifted with a good gift of gab – I was a New York City bartender. But I didn’t have my shit together all the time. I was insecure 50% of the time, and secure the other 50% of the time – it comes with the territory. It comes with being 25.

I remember there was this one girl that I was dating – or trying to date – she was really hot, and I was Needy Boy. I was totally needy. I remember I went out with her on dates, and I was between bartending gigs at the time and didn’t have much money, and I was just being really needy. I really liked her, and I chased her.

I remember calling her one day, and she didn’t respond to me, so then I went to her office and I had no money but hired a guy for two bucks to take a bottle of wine up with a note that said, when are we going to share this bottle of wine? I was needy.

Now I look back at the 25-year-old that did that and I realize I should have just sent the bottle of wine up with a note that said, meet me at seven o’clock tonight in Central Park – I’ll bring the glasses, you bring this wine. See you there! – I should have been demanding. I should have TOLD her what we’d do. But instead I was Wimpy Boy and Wuss Boy and I was always asking.

It comes with the territory – it comes with being 24 and 25. A lot of guys ask me all the time if I could go back to that age, what would I do differently? The only thing I would do if I went back to my twenties is hire the 45-year-old version of me to coach the 25-year-old version of me.

I would find some type of mentor. I know a lot of lessons in life you need to learn on your own, but having a mentor to coach you and work with you really improves your learning curve.

So I’m envious of all the guys that come to me. I love it when the young guys come to me, come to my boot camps, and hang out with me or stay over – a lot of the younger guys can afford the boot camps, but they can’t afford a hotel, so I let them stay at my house. I really enjoy having them in my house. It’s like hanging out with the 24 or 25-year-old version of me!

I see myself in them. Coaching them is easy, because I’m just coaching myself.

So I’ll never actually be able to go back in time, but I feel like I get to go back in time every time I get to coach somebody, and that’s what makes this so much fun.