How to Shoot Your Shot
By: Emma Austin
Tags: Sex, Dating, Life, Advice, Relationships

Unless you have inhuman levels of confidence, shooting your shot probably makes you feel nervous, hesitant, and maybe a little embarrassed.

But it’s still worth doing. Because for all those uncomfortable feelings, it can also make you feel hopeful and optimistic. When it doesn’t go as you hoped, you can still feel satisfied that you tried. And when it goes really well, it can result in some of the best experiences of your life.

As soon as you’re in your teen years and then basically for the rest of your days, your life is going to be filled with missed opportunities, connections that came close to happening but never did, and tons of “what ifs” that exist because you waited just a little too long to tell someone how you feel about them.

That’s why it’s so important to shoot your shot once in a while. Because if you don’t, all you’ll have are regrets.

I almost missed out on some of the best, most exciting, and formative sex I’ve ever had in my life because I was too shy to shoot my shot.

I met a stranger on a train and I fell for him fast. We spoke non-stop throughout the entire ride and I felt a strong connection with him.

I also felt incredibly horny. After hours of deep conversation, I wanted nothing more than for him to kiss me, touch me, and fuck me.

But I couldn’t bring myself to make a move. The train reached the station, we parted ways, and I was left full of frustration and regret.

Thankfully, the stars lined up for me that week and we found ourselves in the same train car again for my return trip. This time, neither of us wasted the opportunity. We found a mostly secluded section of the train and spent the night fooling around, fucking, and cuddling.

It was like a fairy tale moment, but with casual sex.

It wasn’t my first one night stand, but it was the first one that made me realize they could be beautiful, pleasurable, and completely worth pursuing even if they don’t lead to anything more.

And I almost missed it because I didn’t shoot my shot the first time.

And I would’ve missed out on something even better if my husband hadn’t shot his.

I didn’t even know who he was until he sent me an online message out of the blue. I fell for him very quickly and couldn’t stop thinking about meeting him in person.

When I finally got to, that was it. Being with him felt so wonderful that I decided never to leave his side.

So, shoot your shot once in a while because it can definitely work — as long as you do it well. I’ve seen it done the right way (I mean, I fucking married him), but I’ve also seen plenty of backfires and complete misses.

If you want to let that cute girl know you think she’s fine, let that sweet lady know you’d like to date her, or feel compelled to get to know that hot and smart chick you keep seeing online, these are the best ways to approach her.

Actually Introduce Yourself

The vast majority of people trying to shoot their shot are Hey Guys.

Instead of introducing themselves, they kick things off with a greeting. They’ll send a “hey,” a “hey what’s up?” and sometimes they won’t even bother with words and just send a waving hand emoji.

I know they’re just trying to get a conversation started so they can get things going, but a simple greeting is not a strong opener.

If you think someone is clever, sweet, or sexy enough to DM randomly, there’s a good chance you’re not the only guy who’s doing it. She’s almost certainly getting hit up by other guys and she probably stopped responding to most of the messages she gets.

So, you’ve got to do something to stand out so you’re not just a generic “hey” in her notifications.

Whatever DM you send her, it should give a clear indication of who you are.

Most of the time, when someone slides into my DMs, I don’t know anything about them. They could be 20 or 70 years old. They could be somewhere in Canada or halfway across the world. They might have listened to my podcast or read my articles, or they might just be messaging me because they saw me use the word “pussy” on Twitter and decided to go for it.

Unless you’re sure she already knows you, give her a couple of details about who you are. Give her your name if it’s not clear from your handle, show her a photo of yourself (but not your dick) if you don’t have one as a profile photo, and maybe make a joke or two so she can get a quick sense of your personality.

It’s a lot more effective than just throwing a waving hand emoji at her. She’ll feel a lot better about replying if she knows what kind of person she’s replying to.

Make Your Intentions Clear

No one wants to feel like they’ve been whiplashed into a dirty conversation.

I’ve received messages that come across like innocent conversation starters. They’ll be things like “Hey, I have a question I was hoping you could help me with” or increasingly “Hey, I love your podcast!” And sometimes, those are just people genuinely looking for advice or a quick chat.

But often, the guys sending these messages have other motives.

Once I reply, they start quickly veering things into a flirty or sexual direction. They want to talk dirty, they want to see if I’ll have phone sex with them (I won’t), or they just want to share their sexual fantasies in lengthy detail and encourage me to share mine.

At first I found it weird. Why was I getting such G-rated openers from guys who wanted to pivot immediately to something dirty?

Then I realized it was probably a tactic.

They probably assume that I won’t write back to them if they ask me to send them nudes, look at their dicks, or share some dirty banter. But I might if they just want a bit of advice or have an innocent conversation about blogging.

I guess they figure that once I answer their initial messages, I’ll be locked in. When things get dirty, it’ll be too awkward for me to back out, more difficult for me to say no, or make it more likely that I give them the benefit of the doubt even though I can tell they’re trying to lead me down a very dark alley.

And that kind of thing will never work. No one wants to be tricked into having any kind of conversation, especially dirty and flirty ones.

So, make your intentions clear. Tell her why you’re messaging her. Tell her you thought she was cute and wanted to see if she’d be down for a little conversation. Tell her she’s really funny and you wanted to show her a meme you thought she’d like.

It doesn’t matter what it is, as long as that’s the real reason you’re DMing her. Don’t tell her you think her cat pics are cute if all you want to do is talk about her pussy.

Don’t Ask for Her Contact Info

The stereotypical thing to do when you approach a girl is to ask for her number.

It happens online, too. Guys will ask for a girl’s contact info so they can go from DMs to texts. If they’re somehow not phone phobic they might actually want to get on an actual phone call. If her DMs are closed, they might reply to her tweets to ask for a way to contact her privately.

But that’s backwards.

The right approach is to give her your contact information instead. Let her know that you’d love for her to hit you up. Tell her not to be shy and to text you if she feels like it.

That puts the power in her hands. It gives her more agency and lets her decide whether she’ll get in touch with you or not.

When you do get a text from her, you’ll know it’s because she’s genuinely interested, not because she’s replying just to be polite.

Giving her the opportunity to make a move works in your favor, too. She’s more likely to be intrigued by you, think about you, and get curious about you if she feels like she’s invested something in you. That’s what happens when she escalates things by sending the first text. But she won’t get to do that if you’re the only one pushing things along.

It’s also just plain polite and respectful, which shows good character on your part.

And it also displays more confidence, which is another attractive quality.

The guy who asks for her number looks insecure. He’s convinced that she won’t text him if she’s the one in control, so he holds on to it.

When you give her your number instead, you come across like someone who knows his worth and knows he has something to offer. And that’s always more charming.

Assume She’s Busy

The internet is full of screenshots showing men with no chill. They’ll get annoyed when a girl takes longer than an hour to get back to them. Sometimes, they start texting “Hello????” after only fifteen minutes.

That might just be a bit of misguided behavior, but it comes across naive at best and really entitled at worst.

When you’re sliding into a girl’s DMs, you have no idea what she’s doing. But it’s safe to assume she’s doing something.

She might be at work. Maybe she’s fifty texts deep into a debate with a friend. She might be showering or going through her skincare routine.

You could be dinging her while she’s trying to follow a complicated recipe she found on YouTube. She could be doomscrolling while doing a bit of solo evening drinking. Maybe she’s 46 minutes into a movie she’s watching with her cat, doing some online shopping, or fighting on the phone with her mom.

And maybe she’s just bummed out over something and isn’t in the mood to be sweet and flirty with anyone.

It doesn’t matter what it is. What matters is that she’s got a life and she’s living it. And because you’re not a major part of it yet, she won’t drop it all to reply to you the minute you make her phone buzz.

Even if she’s really interested in you, she’s probably putting the same kind of thought into her replies that you put into yours. She might be leaving you simmer because she doesn’t want to look too eager. Maybe she’s texting her friend so they can workshop a really good reply. Or she might follow some arbitrary rule she swears by, like not replying to anyone for the first 24 hours.

The best thing to do is just roll with it.

Showing some patience is good. It makes you seem less desperate, less needy, and like you’re not starved for attention.

Even if she was planning to reply, she might change her mind if she feels like she’s being pushed into it. So, assume she’s busy, ease up on the follow-up texts, and let her reply when she’s ready.

Be Honest About What You Want

There are a lot of guys who think girls don’t want to fuck. So they think the only way to get in her pants is to start playing games.

They’ll pretend to be interested in something sweet and intimate. They’ll act like they want to start a romantic affair with them. Sometimes, they’ll start a friendship and try to slowly build something sexual into it.

If all you want is some casual flirting and fucking with no strings attached, that’s fine. But you should be completely open about that.

Plenty of women are down for casual sex, and if that’s all you want you should make that known.

First off, the girls looking for a one-night stand or a few screws over a weekend might be put off if you act like you’re falling for them. So you might actually miss your shot by shooting it wrong.

It’s also just a dick move. I know some people believe that this is just the way it works, that this is the kind of playing and pretending you have to do to get anywhere with someone. But there are a lot of ways to be seductive and even romantic without being misleading.

Being clear and upfront about what you really want is how you avoid regrets and broken hearts.

If you’re open to seeing if a string of dates with her could turn into a relationship, then you can go with the flow and see where it takes you. But don’t feign falling in love if all you want is to exchange nudes, jerk off on cam with her, or spend a night rocking her world. You’re more likely to actually get somewhere and she’s more likely to remember you fondly for it.

Always Give Her an Out

Feeling unsafe is a total turn-off.

That’s a really big consideration when you’re hitting on someone in public. You have to make sure you’re not standing in her way and making them feel trapped, and it’s best to avoid making a move in any situation where she’ll feel pressure to say yes.

And this applies when you’re shooting your shot online, too.

You can make someone feel unsafe online if you don’t give them an easy out of the conversation.

Let her know that you’d love to hear back from her but you get it if she’s busy. If it sounds like she’s trying to make excuses to leave the conversation, don’t question it and just let her duck out. And if she’s showing very little interest in talking, bow out gracefully.

That way, you can make sure she feels comfortable and relaxed. She also gets to be as flirty and playful as she wants to be instead of worrying that she’ll be stuck in an awkward situation if she does.

If she ghosts, she ghosts. But if she stays, you’ll get to enjoy her at her most fun and frisky.

Take a Chance

I almost never shoot my shot, but that’s mostly because I’m demisexual and almost never crush on anyone. When I have feelings for someone, I usually find a way to let them know.

I’m really shy and I have massive social anxiety. But I also realized all the way back in high school that trying isn’t all that bad.

Showing someone that you’re interested in them, macking on them a bit, or coming right out and saying “Hey, I like you” are good moves. If you do it respectfully and can handle rejection well, it never blows up in your face.

Yeah, you’re putting yourself out there. And yeah, getting turned down can sting. But it’s usually better than always having to wonder what could’ve been. Not to mention feeling like you missed out on a lot of intimacy, romance, and sex.

Like most things, though, you can do too much of it. Pickup artists love to talk about practicing your approach by going up to dozens of girls each day and trying to get their number or asking them out on a date.

That’s a bit much. And most people will be able to tell that you’re taking such a scattershot approach.

But when someone really catches your eye, you develop a crush, or you just feel the urge to know someone and you know they might be open to it, there’s nothing wrong with approaching them and seeing what happens.

You might not have mindblowing train sex or meet your future spouse, but you’ll always be happy you tried.