Is It Too Late To Start Dating After College?

is it too late to start dating after college

Is it too late to start dating after college? What’s up guys I’m Kyle Milligan of and I’m here to change the way that you think about dating. The topic we’re going to cover today is: “Is it too late to start dating after college?” We’ll cover dating and age. College. How to get a date without approaching. As well as Tinder and OKCupid.

The OP on reddit says: He is 23. Never had a girlfriend. Went away for school. On the social side he doesn’t feel very strong. Social awkwardness and social anxiety is a problem for him. He feels will never have another time (after college) in life when he’ll be surrounded by as many single people forced to socialize.

He feels there’s nowhere else he can meet attractive women. He wants to go on dates but relies on Tinder and OkCupid to interact with single women.

Add on the fact that women don’t find him physically attractive and therefore he doesn’t approach girls he doesn’t know.

23 And Never Had A Girlfriend

So this isn’t a question this is a general rant. And what it is, is a giant list of limiting beliefs.

First of before I even address this, I have this one limiting belief exercise that I like to practice that will shatter all limiting beliefs.

So let’s just start here: “23 never had a girlfriend.”

So do you think in the entire world that all 23 year olds who have never had a girlfriend, end up never getting girlfriends? Ever?

We’re going to kind of apply that strategy to all this stuff here.

So you’re 23 never had a girlfriend, huh? Doesn’t matter! Let me tell you why it doesn’t matter.

I hit the dating pool when I was 23. I dated a girl from high school so I never really had to date. I just kind of had like this thing to fall into my lap and it lasted forever. All of sudden I’m single at 23 and I had to do the dating thing like a grown-up.

The thing is you don’t have to worry about finding a girlfriend because first you really got to worry about finding a first date.

Focus your efforts on that. Scale it back.

23 never had girlfriend

You’re putting the carriage in front of the horse. When you figure out how to get a first date, the next step is to figure out how to get a second date.

Deal with that and all the things in between like how to ask her out, how to get her number, before “girlfriend.” First get the date. All these things come far, far before how to get a girlfriend.

So forget the fact that you’re 23 and never had a girlfriend because what you really need to be worried about now is how to get a first date, which is actually a lot easier than you would think.

So you say you don’t feel very strong, socially. You’re socially awkward and have social anxiety… That’s cool and I feel you on that. I’ve been there. I’ve kind of had to fight that my whole life. It isn’t a barrier to success.

Is College the Best Time to Find a Girlfriend?

You worry you’ll never have a time in life when you’re surrounded by as many single people forced to socialize.

So there’s a romanticism about college. Everybody goes there to have sex, like a big giant orgy, non-stop. And they’re drunk it’s all keg parties, frat parties, and sex, right?

The thing is it’s that’s not how it is for the majority of people. People will hook up. A lot of singles mingle in college.

But you’re not the only person who didn’t. This this forum is filled with people who didn’t go crazy in college and they come here and they talk about it like they are ALL the only person to not have 100 sexual partners in college. Do not worry about that.

college best time to find girlfriend

Don’t beat yourself up if you didn’t have a ton of girlfriends in college like this pimp. It’s not the end of the world. Not by a long shot…

As a matter of fact, you’re thinking that your golden days are behind you, or the easiest time to get laid is behind you. Actually, the easiest time to get laid is tomorrow. It’s easier today and if it’s not today, it’s tomorrow. Because every single day you should be getting better.

That is, getting better with women in general. Not just getting laid. You should be improving upon this skill set. You should be stepping up every single day and getting a little bit better.

Keep pushing your boundaries. You should be going on first dates and then the next day or the next week you should be experiencing second dates. And then the week beyond that you should be experiencing third dates.

You need to think step by step here and get out of the whole “I’ve never had a girlfriend,” state of mind. I’ve never had a million dollars bro! I mean I gotta start somewhere. I gotta make five bucks first, right?

Let’s think of it like that. Step by step.

You say there is nowhere else you can meet attractive women… Go to Target! Dude, like go to Whole Foods! Go to Starbucks! Attractive women are everywhere, bro. You just got to open your

How to Find a Girlfriend if You’re A Shy Guy

Let me give you the ultimate strategy to find a girlfriend if you’re a shy guy.

Just go to a coffee shop and go there regularly. Every day. As often as possible. Go frequently. Bring whatever you can to work on, or read. Whatever you do in your downtime. Bring it to the coffee shop find you a spot and post up. Make sure it’s somewhere not in a corner by yourself. Go where you can be in the middle of stuff.

And then every day, because you’re gonna be sitting around people, ask the person nearest you what they’re working on.

Ask the PERSON, not the hottest girl in the room. Not walk up to her or cold approach her and drop some “hey I need a woman’s opinion on XYZ.” No, no.

get a girls phone number in a coffee shop

Tons of attractive girls hang out in coffee shops. Go where your market is.

Just chill in your spot, mark your territory. Get all your stuff spread out and be the man. That’s what you’re doing basically. You’re taking over this location. And then talk to the person nearest you.

Then ask them what they are working on. It could be a girl, could be a hot chick, could be a fat chick. Do this every day, okay? And what you’ll find is that the script comes naturally. That conversation just flows from you.

Then one day, because it’s a coffee shop, there will be an attractive girl there. And then you’re just going to say it to her just like you did with everybody else and that’s how you meet attractive women.

It’s persistence. Dating is a numbers game.

There’s this internet culture and this dating-product phenomenon that I can sell you the secret line to go get any girl you want. The girl of your dreams! The secret tip!

No, no, it comes from a million little efforts and building that confidence.

You create a pattern of behavior in your head, and you know exactly what’s going on. See, that’s the thing, if you keep saying the same thing every day and you kind of get a flow in there, you’ll start to feel comfortable.

It will breed confidence because you know where that conversation is going. You’ve had it a hundred times.
Trust me, man. Sit in a coffee shop. Ask the person nearest you what they’re working on. Do it every day, you’ll be going on like a date a week.

How to Ask a Girl Out

Let me go ahead take it a step further. I want to tell you how to ask a girl out.

When you talk to a good-looking girl just talk to her like you would anybody else. And basically you’re just interviewing her and you’re trying to figure out if she would be someone that you would want to hang out with.

Forget her looks, forget what she looks like or any of that, just be asking about her. Be listening a lot more than talking. Try to figure out more about her and in the moment she says something that sounds really relevant to you, be like, “oh yeah, I know. Have you been kayaking? Have you been to the waterpark with the rapids?”


You’re just interviewing her. Then when she says something interesting you can just say, “I actually have had a really good time chatting. Would you like to hang out sometime? When are you free on Thursday?”

That’s how you ask girl out. It’s really just simple, direct, straightforward asking her out.

I’m not here to sell you a product or plan or prescription for how to get girls. That’s really how it goes. If you’re a genuine dude and you guys did make a genuine connection over that conversation, ask her out.
You need to know two things when asking a girl out:

  1. A time
  2. A place

When you ask her out say, “Let’s hang out on Thursday. Are you free at seven? Cool, let’s go to Joe’s at seven.”

A time and a place is all you need, alright?

Is Tinder a Waste of Time?

I do really want to go on dates but I rely on Tinder and OkCupid to even interact with single girls.

Look, you’re not too good for Tinder, okay? I think there’s this stupid thing like the college thing. it’s just a stupid stigma. Tinder is great. OkCupid I don’t use OkCupid but I know some guys who have and they say it’s great.

I’ll tell you what tinder and OkCupid are, they’re sources of traffic. If you’ve ever been in sales you take whatever leads you can get from wherever you can get them.

That’s how you need to think of online dating. OkCupid is a lead source. It’s a traffic source. Whether you go to the coffee shop, you can go to the club, you can go to the bar, you can go to I don’t know, Target or whatever.

Guess what? Those women are all women. Regular, human women. You just found them at different locations. Different traffic sources. Different sources of defined leads. That’s all Tinder and OkCupid are.

So get it out of your head that it doesn’t count if it’s Tinder. Or if you think it’s only whores on OkCupid or whatever.

Because at Target there’s going to be some whores, right? So would you say meeting a girl at Target doesn’t count because somewhores shop there? Same thing with online dating.

There’s good people and bad people everywhere. Tinder, OkCupid, Target, Coffee shop, you just gotta take the good with the bad.

Insecurities – I Am Not Attractive

Next thing you say is “most women don’t find me physically attractive.”

All right I can relate that’s kind of what I struggled with.

So all my life I struggled with the fact that I was five-seven and I started balding at age sixteen.

That always bugged me. All the tall guys with great hair lines will always get the girls and I was never good enough. Not to mention I grew up in a trailer. Yeah I was dirt poor my whole life. That pretty much sealed the deal.

I mean you went off and went to school and get five years of undergrad so you might have came from money maybe.

What I mean is that I could easily have found a way to make you better than me in my head because I was insecure about my height, and my hair, and my wallet. Everybody’s got their thing man, so you’re saying women don’t find you physically attractive.

You can join a gym. Everyone’s going to rush to say get big muscles, that doesn’t make you really any better because there are dudes with giant muscles in the gym who hit on chicks all the time and it doesn’t work.

Because what really matters to women is different than what matters to men. Men are totally triggered visually. You have to be like a really really dumb chick and really really annoying a psychotic and if you have like a certain level of hotness guys won’t even care.

What Women Really Want

It’s not the same for girls. For girls, it’s like if they catch you slipping, they catch you acting like a bitch who doesn’t find himself physically attractive, they’re done with you.

Whether women know it or not, above all else they want three things:

  1. Confidence
  2. Directness
  3. Congruence


Okay you need to work on at least confidence. You need to be confident that physical attractiveness is subjective. And you’d be surprised, the girls you can get if you have some swag. If you’ve got cockiness in your step. If you’ve got some attitude and some sarcasm in your jokes.

Man chicks eat that up. So get more confident in who you are, in your game, and just know who you are.

Models Mark Manson

(Related: My favorite book on attracting women with honest confidence – Models by Mark Manson)

Check it out on amazon


The second thing you need is directness.

The directness aspect is in regards to stating your intentions. So if you are talking to a girl at the coffee shop and you like her so you ask her out. That’s direct that’s when you say, “hey, you know, I actually had a good time talking to you I got to go but would you like to hang out. Are you free on Thursday?”

That’s a direct ask out. The indirect ask out is you facebook her later or something really weird like that. Well she’s not sure where you’re going with this. Are you going to ask her out? Do you like her? Do you not? Like that’s indirect. It’s weak.

It shows that you aren’t confident enough to ask her directly because you’re afraid of rejection.

So remember, be confident and direct. Last thing is congruence.


Congruence is when you ACT out your thoughts. Almost every guy messes this up because this is where indirectness stems from.

You see a pretty girl you want to talk to. And you say something stupid you like this…This happened the other day there’s a girl standing and she’s got a tattoo on her arm. A dude walks up he says “You’ve got something on you.”

And she looks and says what and he says “It’s your tattoo. Ha ha ha.”

And this guy is laughing because he’s too big of a fucking pussy to say, “hey, how’s it going? My name is XYZ.”

That’s what a confident male would do, is walk up and introduce himself because he wants that girl. An indirect man will make up some excuse, some lame joke, or something stupid that he think is witty. Because he’s afraid that she’ll say actually I’m not interested and that’s the worst she can say if he would just be a confident man.

Congruent guys like a chick and talk to the chick. They think, “I like this chick and whenever I find out if she’s a cool chick I’m gonna ask her out.” And then he does it.

That’s the congruence. It’s the follow-through. The follow-through of confidence and directness and that will take you to promise land. That’s the that’s the endgame once you get confidence, directness, and congruence down pat.

Forget physical attractiveness man. It matters but to an extent. But just like rich guys get chicks and jerks get chicks. It doesn’t matter that they’re fat or sometimes ugly. If they’re rich and they’re a jerk or something like that.

What that boils down to is it’s not the riches. The riches bring the CONFIDENCE.

Chicks don’t like jerks or are attracted to a guy because he is a jerk. Girls like jerks because they’re confident. They don’t apologize for anything. They just they always know who they are, what they’re about, and they never back down from that.

Cold Approach

You say you don’t approach girls you don’t know. That’s fine and I think what’s the problem is there’s another romanticism here with the whole cold approach, pickup community. And even in these forums there’s a lot of keyboard warriors who’ve never really gotten any dates or are going out with chicks, but they’re trying to explain the right lines and appropriate ways to run game.

When at the end of the day, sure, taking massive action does help and approaching a million girls will get you there but it’s also going to get you looking like a real weirdo and ruin your confidence and your self-esteem. Because when you act like a weirdo, when you act out of place, and wacky, people are going to be a lot more self-righteous about bringing you down a peg.

However if you’re just cool and genuine human who wants to talk to a girl and you just do it by saying something like “hey my name is…” something like that, just to walk around say your name and just something as simple as that.

I think if you aren’t ready to do that, if you don’t really want to walk across a crowded coffee shop and say something to somebody like that, your best bet is to do the strategy I told you at the very very beginning.

So sit your ass in the chair at the coffee shop all damn day and talk to the people that surround you. And don’t and you don’t have to have a 40 minute conversation for this to be a success.

Pat yourself on the back if you just ask the question to get the conversation started which is, “hey, what are you working on?” And you’d be surprised. People will talk to you. Old guys will talk your ear off.

Man I practice what I preach. Old guys will talk your ear off one dude started and told me like for two hours the the good days of real estate for him when he was mogul and somebody and how the stock market screwed him over.

Like I asked the question and we were off dude like he wouldn’t let me get back to my work! And that could be anybody.

It can be a hot chick, it can be old people, can be a fat chick, it could be a regular Joe. But if you just talk to people you’d be surprised.

Dating Is A Number Game

Dating is a numbers game. Meeting girls is a numbers game alright? It is the summation of a million little efforts. It’s not just go out and meet a girl thing. It’s not like this magic line. It’s not just like we’re out approaching hot chick, hot chick, hot chick and then they all say yes.

Talk to a bunch of chicks. Some are receptive, some are not, and then you gotta close the ones that are. That’s it.

The ones that are not receptive usually don’t make a big deal and shoot you down.

They’ll be like “man I’m busy” because you’re behaving like a normal dude. You’re just wondering what they are working on and seeing how they respond to you.

Don’t do one of those pick up things that people do, where they sit there and they just drill the chick with questions or something. There’s a there’s a term for it where you face through resistance or whatever, but that’s probably a bad idea more often than not.

I used to really study this stuff. I’ve done it all I’ve been there. I started the dating game at age 23 myself. So I was in the same boat as you. You can do it. You need to get rid of all these limiting beliefs.

I spent all this time chatting with you because these are all limiting beliefs and I wanted to debunk these. Don’t come up with new limiting beliefs now. Just put into practice the shit that I just told you and you’re going to be fine.

The time to learn to talk to chicks is always the future man, you’re going to get better every day as long as you practice. You take action. Don’t think that just because you talk to girls that you’re gonna land the chick, right here, right now.

I’m Kyle Milligan of We just tackled “is it too late to start dating after college?”

Thanks for watching and reading!

Is It Too Late To Start Dating After College? - Real Kyle Milligan
Article Name
Is It Too Late To Start Dating After College? - Real Kyle Milligan
Is It Too Late To Start Dating After College? We'll cover dating and age. College. How to get a date without approaching. As well as Tinder and OKCupid...

About the Author Kyle Milligan

I'm Kyle Milligan, I write New Adult Books that don't suck. i.e. The Hang-Ups and Hangovers series. I like to write about the challenges of being a single twenty-something in today's hookup culture. My blog offers Dating Advice For Men.

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