Tripp, this last week I saw a high school crush that I can't get out of my head. I'm a 27 year
old single dad. My daughter is 8 and had a week long softball camp at a center that this person
manages. I know her from Middle and High School and haven't seen her much at all in the past 10
years. The problem is, I've never actually spoken to her. Every time I try to convince myself to
talk to her, I chicken out. I even jokingly told my daughter, I thought she was cute and she wanted
me to go talk to her. I just couldn't do it. One thing that is really intimidating about her is
that she's been single for many years. I'm an average, almost overweight guy. Why would she
choose me over the athletic trainer she works around every day. I feel like an asshole for
basically not even acknowledging her at all last week. I want to message her on Facebook and say
something like, I didn't want to bother you at work, would you want to go out and grab a drink
some time? But now I'm worried she'll think I was too afraid to go up to her, I was, and waited to
do it online because it's easier. No idea what I should do here, but It's eating me alive that I
didn't approach her and now I'm concerned I'll never get that opportunity again. I've always
been really nervous about talking to girls, but this situation is different and I feel like I
screwed up. Hopefully I'll hear back from you. Thanks, Mike." Okay, Mike. Great question man.
Per usual, just a rich question. I have a lot to say. First of all guys, Mike included, the reason
why you need to go out and approach more women and always be approaching and always practicing this
is because you want to be prepared for this moment. I remember when I was going out
trying to meet women, before I was doing my mass approach days where I was going out and
approaching a lot of women, but I knew a little bit about meeting women and game and pickup and
talking to girls and all this stuff and I had very little experience, and I remember I had
these exact moments that you had, by the way, Mike. I would have these exact moments. Not with
a daughter and softball camp, but these moments where you see a woman and you see her a lot and
you want to approach her, you want to talk to her, and you just can't do it, you're so scared.
And it's funny because then after doing my mass approaching, a moment like that would
seem so silly to me now that I had the reference experience and the practice of talking to women.
Guys, you're shooting yourself in the foot if you're not going out and practicing talking
to women because you're going to have a lot of moments like these in your life, where you see
a woman wherever it may be, in this case for you Mike, your daughter softball camp manager,
and you're going to want to talk to them. I know that doesn't answer this question specifically,
we'll get to it. But that has to be said, you need to be working on that. Mike please, guys please...
go out there and talk to women. They want you to talk to them.
I just talked to my friend who was on the podcast. Her name is Stephanie Daly. You can check her out
on Instagram. She does all these polls. She polls her audience, men and women and gets
their opinion on things. And she polled and asked women "do you want to be approached?" And the
insane majority said yes. They do want to be approached, they do want to be talked to.
So there's that. Now, let's talk about this specific situation. You are correct. You should
not be trying to get her on Facebook. First of all, the conversion is really low there.
I haven't heard of or even experienced a high conversion in messaging on Facebook and
converting that to a date because you're trying to play the game that you think... you would play
where a woman would message you and you'd be like, she's really attractive and then you'd
say yes or no. That's not how it works for women. They need to see your personality.
They're going to judge you by your looks. And you're not even going to get a chance at all to
build attraction. And a bunch of other reasons we don't have to go into. But the reason is it's
just low conversion. It's low conversion so because of that, you need to make sure
that when you see her next, you start a conversation. The best way to do this is
when you see her, you want to say anything... literally anything. It doesn't even matter.
I can give you something canned... I'm trying to think off the top of my head. I mean,
ask something about the softball league. Ask something about... are they doing it next year?
I don't know, it doesn't matter. Literally come up with anything and then just talk about it.
It doesn't have to be something casual. It can be something about the work.
In fact, it probably should. I think it'd be a little strange if it wasn't.
Just talk about anything, just get words out. I think the easiest way to do it would be to
talk about something like next year is there a league happening or other other leagues or
whatever it may be. I want you to go up, talk to her, and ask that question. Now in terms of
the motivational aspect of it, I know that it can be very scary to do this. And one of the reasons
why it's scary for you is for what you basically said, underneath some of the things you said here.
Which was I'm an average, almost overweight guy, why would you choose me over the athletic
trainers she works around every day? Which is what you're saying between the lines is that
you don't feel deserving of a woman like this. Therefore, you're thinking way too hard of
what to say. A guy who feels deserving of a woman that he's attracted to wouldn't be thinking that.
He would just say, whatever. He would just go up and talk to them and it wouldn't matter because he
knows that he has enough value. You're putting yourself below her. You're putting her... A,
you're putting on a pedestal, but also you are diminishing your own value.
Now, maybe she would choose the athletic trainers over you. I don't know. She might.
I'm not gonna give you bullshit motivation and say, "No man. She doesn't want them. She wants
you." That's... who knows, I don't know. But the point is, don't enter that into the conversation.
Don't let that be any sort of mindset or any thought or rumblings at all
in your head. Yeah, maybe she would. Or I don't know, maybe she likes guys who are overweight.
There's women out there who are called chubby chasers and they like guys who are bigger guys.
So you know what, maybe she wouldn't want you because she'd want a guy who's even more
overweight, or maybe you're her perfect type or who knows? Don't think about that. And if,
by the way, that is something that bothers you so much, then you need to be working on that.
We talked about that earlier on this podcast. We talked about the idea of always
optimizing your looks and your health. That should be something that's on the forefront,
especially if it is something that bothers you and is affecting your self-esteem. But that's a
whole other conversation. The point is, you don't know what she wants. But I will tell you this,
I'll tell you what she does want and this is a fact, she wants a charismatic guy.
She wants a guy who's not going to be scared, she wants a guy who's not going to be
messaging her on Facebook. She wants a guy who's going to display his personality.
And that guy can be you. And so the sequence of events that I would do is
I would spark that conversation with her, whatever it may be on any topic regarding the league,
the work that she does, a question, an inquiry of some sort. And then the next time you see her,
you can start talking to her again and say, "Hey, what's going on? Good to see you. How
are things going? So now it's not going to be such a strange introduction anymore. You've
already talked to her, you've already laid the groundwork of who you are and there's a little
bit of information there in the sense for her to think about because she's referenced you. And
now would be the time to ask her out. I have a great line for you. You can say, "Hey, you know
I know this is random. But why don't you and I grab a drink some time?" I wouldn't start that
as the conversation for the second conversation. I would go up to her and spark conversation and
just say, "Hey what's going on? And how are things going?" and good to see you again
and then after a little bit of conversation, just say that and then see what happens. I guarantee
you, after you do at least the first approach, just coming up with anything that you can,
it's going to be a lot easier the second time around. And you're also going to
start building self-esteem because you're going to feel so good that you did it.
And this, we don't know if it's going to work out, we don't know if she's going to be interested.
But maybe this can be that first push where even if it doesn't work out it gets you out there. And
it starts the process for you to get going and talking to more women and getting dating again.
Wow. I completely looked over something that you said here. You said that you saw your high
school crush. You knew her from middle school. So dude, you have your opener right there.
It was right in front of you the whole time. Here it is, you go up to her and you say, "Hey
Stephanie", or whatever her name is. And she'll be like yeah and maybe she'll remember you.
And if she goes, yeah and she goes do I know you? Say, you went to blank blank middle school and
high school right? And then she'll say, yeah and then say it's me, Mike. I don't know. You
didn't mention if she knew you or not. But it's me, Mike or you can say yeah, my name
is Mike and I recognize you. We went to the same high school. And you can say, that's it. Boom,
there you go. That's your in right there. Simple as that. And again, if you didn't have that, then
I would have talked about something going on with the league and just get into conversation there.
Hope that helps Mike. It's a good one.