Category Archives: Talking to women

How I stopped being socially awkward

It’s been a while since my last newsletter, huh? Life’s been absolutely hectic these last few months. I’ve just moved from Milwaukee, WI to Chicago, IL to be closer to my family. It took several weeks of packing, cleaning, loading, unpacking, and cleaning again, but it’s finally done…mostly. There’s still several boxes of stuff sitting by the front door and I’ll get to it eventually.

Well, that’s still not a good excuse for missing so many weeks of newsletters. As per Quietly Romantic tradition, if I go too long without releasing a new blog post or newsletter then my next one needs to include an embarrassing story.

Here we go.

MFW I get to share something embarrassing about myself on the internet.

A few years ago, I was at a conference and I had the opportunity to meet one of my heroes in person. He was a huge source of writing inspiration for me and was someone that I really looked up to. Think along the lines of…meeting Stan Lee, if you’re a fan of the Marvel superhero movies…or meeting George R.R. Martin, if you’re a fan of the Game of Thrones series. Yeah, that huge.

He’s an intelligent person, and there are so many things I want to learn from him.

  • How does he write so well?
  • How did he attract so many fans?
  • How does he come up with such amazing topics to write about?

He arrives at the conference, gives a presentation, and afterwards starts interacting with some of the guests. I wait in line, fidgeting all the while. Finally, it’s my turn to talk to him. I stagger up to him and shake his hand.

“Hey, I’m Steven. I’m a huge fan of your work! It’s good to meet you”, I exclaim.

“It’s good to meet you too,” he replied. “What do you like to do?”

“Umm…I like…video games?” I mumble. He replies with a deafening silence. “…And I also like reading?” I continue.

His feet start to shuffle away from me. “Well, it’s good to meet you Steven. Best of luck.”

“Yeah…good to meet you too,” I reply, hiding behind a smile of feigned pleasure.

Welp. Something went wrong, but I didn’t understand why at the time. I paid a lot of money to attend this conference just so I could meet him in person. And this is what I get? For weeks after this encounter, I just told myself that I never should have met my hero in person because he was a jerk.

But now I’m older and wiser, and I realize that I was the awkward one in that conversation.

Oh Steve, you were so young and dumb back then

If I could go back in time, there are three ways I’d change the past:

  1. Kill baby Hitler. This is a given for time travel, right?
  2. I’d stop myself from watching the Chicago episode from Stranger Things season 2. I mean…I love Stranger Things, but what even was the point of that episode??
  3. I’d tell myself what I’m going to share with you in this newsletter today:

Here’s what I know now that I wish I knew before.

Continue reading How I stopped being socially awkward

Socially weird or awkward? You better read this!

Today, I’d like to share with you four social blunders that I used to make with women all the time. I’ve had women not want to go on dates with me specifically because I was doing these.

The worst part about being socially awkward is that when you’re making a social blunder, people tend not to tell you. It’s considered rude or impolite to let someone know that their behavior is coming off as weird. Instead, people will do their best to act like nothing is out of the ordinary and secretly continue to let you come off as weird.

That’s why for a long time, I didn’t even know that I was being socially awkward or weird! Ah, well.

Continue reading Socially weird or awkward? You better read this!

Not a fan of cold approaches? Me neither. Try this instead!

I’ve never been a fan of cold approaches. Back when I was single, I always worried that I needed to “get good” at doing cold approaches in the same way that James Bond or Han Solo was if I ever wanted to find love. And I never liked that idea. I never wanted to be that guy who approaches every woman he sees in public places.

Cold approaches can work for those people who are more extroverted or who frequently hang out at bars and clubs. But for introverts, I don’t believe it’s the best way to get a date.

Usually when we think of flirting, we think of innuendos and playful touches with plausible deniability. You know, the kind of things people do when they’re trying to take home someone that they just met for the first time at the club or bar. And that’s fine, but it’s never been my cup of tea.

Instead, I propose my new HSP approach. This is good if you’re an introvert or a Highly Sensitive Person (see what I did there??) It’s inspired by Jeffrey Hall’s book, The Five Flirting Styles. In his book, Hall identifies Sincerity and Politeness as two perfectly valid forms of flirting—especially suited for introverts.

Continue reading Not a fan of cold approaches? Me neither. Try this instead!

The world’s most foolproof way to tell if she’s interested in you

Recently, I’ve received several emails asking me something along the lines of, “She did this when talking to me. Does that mean she’s interested?” My answer to these is always the same.

There’s one foolproof way to find out if she’s interested. That is to ask her out.

Seriously. I wasn’t there. I have no idea whether she’s interested in you. I know even less about her than you do!

Now, if you would like some help or advice around asking her out then that’s something I can help out with. But if you’re interested in someone and you’re wondering if she might possibly want to go on a date with you, my answer is always the same.

Just ask her out already!

Use these exact words to get your next date

I’m back, baby!

It certainly has been a while since my last article, hasn’t it? Throughout the summer, I’ve been taking a cross-country road trip from Wisconsin to Montana. Also, I’ve become fully convinced that North Dakota does not exist.

Seriously. I drove to the spot labeled “North Dakota” on the map and there was nothing there. What gives?

Today I want to share with you a script that you can use to get your next date. The next time you’re talking to a woman you’re interested in, feel free to use these exact words to ask her out. I’m going over this with you because there are a few good ways to properly ask her out, but almost infinite ways to suck at asking her out.

Continue reading Use these exact words to get your next date

You don’t need a reason to flirt with her

I recently got a message about a post I wrote a while ago about flirting. I wrote that when I’m talking to a woman for the first time, I like to lightly touch her on the arm and see how she reacts. One of my readers wrote to me, “But like do you just touch her in the middle of conversation? There has to be a reason for it, no?”

My response? You actually don’t need to have a reason.

This hits close to home for me because I used to struggle with this a lot.

When I was going to kiss my future fiancée for the first time, I was super nervous and super hesitant about it. The moment was right. The mood was right. But I still felt like I needed a reason to do it. So, instead of just doing it and kissing her for the first time, I just kinda let my face hover in front of hers for about half a minute. Like a weird statue.

She still teases me about it to this day.

When it came to interacting with women, I thought that if I was too forward with her or I came on too strongly then I would come off as a douchebag. So, I always thought that I needed a reason to flirt with her or to go up and talk to her or to grab her hand for the first time.

You don’t need a reason to do any of that! It’s okay to just do it.

Obviously, you do want to be aware of social boundaries. Don’t try to grab her or kiss her before you’ve even met her. That does make you a douchebag and hopefully you already knew that.

However, it’s okay to be bold when interacting with her romantically! If you’re talking to a compatible woman then deep down she already knows there’s a possibility that your interactions might become romantic. (And you know what? If you’re lucky enough that’s she’s interested in you as well, then she’s hoping for a romantic interaction!)

So, touch her lightly on the arm as you talk to her. Hug her at the end of the night after your date. Kiss her when the time is right. There’s no need to half-ass your romantic gestures by needing a reason for any of that!

How to stop running out of things to say when talking to her

A long time ago, I remember trying to start a conversation with a woman who I thought looked kinda cute. It went something like this…



“How are you?”

“I’m good. How are you?”

“Good, good.”


(Uh-oh, awkward silence! How do I keep the conversation going? What do I say next? Do I make a joke? Should I comment on how she looks? Think, Steve, think!!)

“So, the weather’s pretty nice,” I muttered. (The weather? Really Steve??)

“Yeah,” she replied.


“Umm, I need to go,” she finally said. “Nice talking to you” she halfheartedly added. Well, crap. It only took me about 30 seconds before I completely ran out of things to say to her.

How do you overcome the obstacle of running out of things to say when talking to women?

Continue reading How to stop running out of things to say when talking to her

What are you supposed to talk to her about?

A long time ago, I used to have a crush on a woman that I saw every day on my bus ride home. I wanted to just go up and talk to her but I was always afraid to. Mostly because I had no idea what I was even supposed to talk to her about.

One day I decided to just go for it. I remember it going something like this:

“Hi”, I sputtered nervously.

“Hi,” she replied.

I felt my heart racing at a million miles per hour. Oh jeez, what do I say next?

“Umm…what time is it?” I muttered. Really, Steve? The time?! You couldn’t think of anything better?!?

“It’s 3:25” she replied.

“Oh, ok” I responded.

A few minutes passed. We arrived at her stop. She got up and walked off the bus. Well, crap. I slunk down into my seat, buried my face in my hands, let out a long sigh, and started hoping that nobody witnessed my dismal attempt at talking to her.

What are you supposed to talk about when you’re talking to someone you’re interested in?

Continue reading What are you supposed to talk to her about?