dating advice for introverted men

Fellow introverts, my dating journey has been one of the toughest, hardest obstacles I’ve ever had to deal with in my life.

I’m not here to complain.

I’m here, first, to relate. I know there’s plenty of dating advice online but it likely hasn’t worked when you tried it. Or it is so far off from how you naturally are that you don’t even consider trying it.

There’s so much advice out there that has good intentions but just doesn’t hit the mark. You can easily feel frustrated, angry, or even resentful, as I have. This is because you’re told that “this is the only way” but it just doesn’t seem to work.

I’ve been told in the past that “all that is holding you back is the courage to ask women out.” But when I started asking them out, I kept getting rejected.

You may even still have faith in advice that isn’t working, hoping that your results will change. But I’ve already experienced where that road leads for you. Decades later, you’re not much better off.

Rather than give you an exhaustive list of all the advice that didn’t work and what to do instead, I want to highlight the most impactful tips to change your dating life as a shy introvert.

1. Don’t Just Be Yourself. Be Your Best Self.

A recreational co-ed sports league seemed like a slam dunk of an idea in theory.

You get to meet beautiful women your age wearing skimpy outfits while playing volleyball in the sand. Plus, it’s more relaxed and less aggressive than a bar or nightclub. For introverts, you actually have a chance to casually introduce yourself and talk to others.

Another great “idea” is to be yourself. Women love giving this advice because they hate it when they sense someone is being fake. It’s a turn off and they might have been snubbed by someone dishonest in the past.

But how does it pan out in reality?

When you’re playing the game, there’s no time for talk. When you’re waiting for a court to open up, there are opportunities to chat. But as an introvert, if you just sit there quietly, no one will talk to you.

Once in a blue moon, someone will try to make conversation with you but it’s almost always a guy. The girls just talk on their own.

By being myself, I sat there without saying a word. Maybe I was scared of talking to someone and getting rejected or maybe I was scared I wouldn’t have anything to say, I don’t know. But I went most of the season like that.

Maybe people will come up and talk to you when you try it.

What Works Better

But what matters more than random advice is being observant of how the world sees and treats you. And for me, it became a clear pattern throughout many events that I am more ordinary and invisible than my ego likes. Most people just don’t even notice me unless I make myself known.

Being yourself doesn’t mean being your shyest, most reserved version of yourself that you’re most comfortable with.

That leads me to the next advice I want to highlight.

2. Don’t ‘Just Do It’. Do a Little, Then a Little More.

“Just meet new people. Don’t worry about approaching or asking for their number.”

This is great advice at the beginning. I heard it from Tucker Max, a successful entrepreneur, and it was a great way to get over the fear of talking to women or intimidating people.

While it didn’t cure all my fear and paralysis, it definitely reframed my interactions and helped me interact socially much more like a normal person.

But my fear of hitting on someone who is not interested led to a lot of two sentence interactions with new people.

I was scared that girls would immediately detect that I’m hitting on them even if I just engaged them in small talk. I imagined them rolling their eyes, and cutting the conversation off cold. Therefore, my interactions became about getting the rejection over with, while spending the least time in an interaction.

This meant me saying something like:

“Hi, What’s your name?

My name is Will.

What do you do for fun? [or] How did you come by this [insert hobby or event]? [or] What breed dog is that?”

And then, I would turn and leave.

When I’ve tried this at Latin dance classes, yoga classes, and so on, it doesn’t lead anywhere. But I had hope.

I continued doing this for months … but all of a sudden, it had been 2 years. And I wasn’t making the progress I wanted to.

In fact, I was getting zero conversion into dates or anything romantic.

Now, I could sit and theorize why this was until the cows come home (maybe it was because I was the only Asian there and they didn’t see me sexually or I was coming off too weak or blah blah blah), but that wasn’t going to help unless or changed my behavior.

Therefore, I tested new stuff out because I knew nothing would change if I kept repeating what I did.

Here’s what worked:

Try giving compliments, taking more time to talk to them, and not hiding the fact that you’re being sexual.

Dr. Robert Glover is the best-selling author of the book No More Mr. Nice Guy, and has coached thousands of Nice Guys as a psychotherapist. He found that one key problem Nice Guys had was that they were ashamed of showing any sexual motivations in their approach or interaction when they shouldn’t be.

You might think, “But what if she thinks I’m hitting on her?”

Well, you are hitting on her.

Finally, close the deal. You have to make some solid, clear attempt that you’re interested in her romantically or you’ll always wonder if the girl even got the hint, especially since you aren’t in a nightclub or bar environment when the social context makes it more apparent.

Ask her out for coffee or tea once you get to know her. Or if that’s too much, compliment her on something.

3. Don’t Follow Strict Rules. Bend the Rules

When something doesn’t work, try something new. I’ve learned the hard way that banging your head against the wall by repeatedly following someone’s advice that isn’t working won’t lead anywhere.

A lot of advice is designed to be all-encompassing and reach the masses. The problem is that you’re an introvert and you’re unique. You have specific situations that require tailored advice.

But sometimes, the world doesn’t have the tailored answer for you on a silver platter. You have to use what you got and try out new stuff.

For invisible introverts, that can mean going out of your way to make yourself known and show why you’re attractive to women. Because otherwise, you remain that invisible man that goes unnoticed.

It can also mean innovating on the advice already given. Maybe a soccer league wasn’t the best idea because there was little time to converse. But maybe a casual kickball or bocce league would be great for you.

The Golden Pill

As an introvert, the most powerful advice I can give you is to:

Have a positive mental attitude as much as possible. Don’t feed resentment, anger, or bitterness because they will cripple you.

Improve your weaknesses. If you’re skinny, go to the gym. It may take years but it’s worth it. I was frustrated at my slow progress working out but it’s finally paying off after many years. If you don’t have much of a personality or interesting life, try out improv classes or something new. By constantly improving your value, you will attract higher quality women.

Don’t hold yourself back. I’ve spent decades learning the hard way that just sitting back and staying quiet leads to little to no results. Maybe you’ll be luckier than me but rarely did any girl ever engage with me first until I talked to her. Keep it going when you see positive signs.

Take these with you in the world and good luck to you! I wish you the best and I hope you see results.

What’s your biggest struggle as an introvert? How do you plan to use these tips to improve yourself? Let me know in the comments.

Will you laugh

Will Chou is the creator of Will’s Personal Development Blog, a personal development site for Asian Millennials, where he shares the top lessons he learned from studying the most successful people and companies in the world. Will has a gift for Introvert Spring readers. Get Will’s morning habits check list to stop procrastinating, get immediate focus, and boost your productivity.