Best dating sites for shy guys

The best dating sites for shy guys are the ones that make it easy to chat with people without having to go through the whole “putting yourself out there” process.

I know it sounds like I’m bragging, but I’m not. It’s just a fact: shy people don’t like putting themselves out there. And yet, if you want to find a date, you do have to put yourself out there—at least a little bit.

That’s why the best dating sites for shy guys are the ones that make it easy for you to just jump right into the conversation. You can start chatting with someone without having to worry about whether or not it will be awkward or how much time you’ll need to think about what to say before saying anything.

Best dating sites for shy guys

Woman at Cafe - Online Dating

Successful Online Dating for Introverted Men

What successful online dating looks like.

Let’s start with an overview and frame of mind about online dating for reserved and/or shy people, so the rest of the article is contextualized for you.

Here are five principles we hold dear when it comes to online dating for introverted men:

Principle #1: Be Selective

No matter what dating app you use, quality is more important than quantity.

Dating is not a “numbers game” in the sense that “the more numbers, the more it will magically work out!”

Rather, dating is an exploration of whether there is a quality mutual fit.

That requires a number higher than zero, but it is not a “numbers game” in the way many people (who are less oriented around genuine connections) think of it.

There are plenty of fish in the sea, but what good are 50 matches if they are all the OPPOSITE of the kind of woman you want?

It’s better to have 5 messages from a woman who seems very attractive to you on multiple levels than 50 messages from less than that.

So how do you determine quality?

Here are a few quality markers to help you be more selective:

  • You’re attracted to her profile photos.
  • You have common areas of interest/passion.
  • She shows attention to your profile details in her responses to you.

By being thoughtful and selective about who you message online, you’ll be better able to discern the value of the platform for your particular tastes.

You’ll also end up going on better dates!

Principle #2: Notice Photo Details

Have you ever shown up to a date with a woman you met online, only to see that she looks NOTHING like her profile photos?

That’s frustrating.

It’s also largely avoidable.

If you are particularly discerning about her photos, you can catch a lot that you wouldn’t have noticed at first blush.

This will help you decide if she seems consistent and reliable enough to message.

It’s not a good sign if her photos show her in…

Wildly different times of life: for example, huge age differences between photos or extremely different hair styles and colors, implying a significant time difference between photos. This often means everything you’re seeing is not completely current / accurate to today.

Hard-to-see angles and lighting: for example, photos taken from the neck up or photo angles in which you can’t discern what she actually looks like. While looks aren’t everything, they are important to showcase honestly. Otherwise, what’s the point?

Principle #3: Present Well

It’s important that you present well from moment #1 all the way through, especially with something premeditated like your online profile and with your style in general.

A shoddy photo is not an in-the-moment hiccup. It’s a premeditated hiccup, meaning you had plenty of time before you decided to publish your profile, and plenty of moments since.

I’ll go over how to present well in your photos, profile, and messages here in this guide.

For now, I just want to establish it as an important principle in online dating for introverts, and anyone for that matter.

Principle #4: Be Genuine

What good is a profile that gets lots of attention if it doesn’t line up with YOU and who you are?

How awkward would that be on dates?

I know of a dating coach who writes online dating profiles for clients, and the profiles end up being the dating coach’s unique voice, NOT the client’s unique voice.

Why? Because the client didn’t write it!

One such client told me his dates would say to him (confused and put off) that he had 3 personalities:

  • one in his profile,
  • one in his texts, and
  • another one in person.


He had been copy-pasting “techniques” from 3 different dating coaches and hodgepodged them together.

This is not a solution.

The solution is to find YOUR unique voice and showcase that skillfully across platforms: online, texts, in person, everything.

Because of this, at Introverted Alpha our coaches co-edit and co-finesse a profile with each client. We don’t write it for him.

We uncover what is uniquely attractive about him and walk him through an exercise similar to what is in this ebook.

Reason being, women are going to go on a date with HIM, not us!

Principle #5: Communicate Well

Dating, like business, is communication.

Every human-to-human interaction depends on it, including online dating for introverted men specifically.

We’ve written a guide on conversation topics and tips for introverts, so you can refer to that in preparation for your dates.

Here in this article, I’ll teach you how to do this here in the profile and messaging section of this guide, and also in the photos section because visuals are communication too.

You’ll want your written communication to center around…

  • What is most attractive about you
  • What you find attractive in a potential match
  • A sense of what it would be like to be with you

Your visual communication is through photos, which should include…

  • A good mix of photos showing different aspects of your life
  • Photos with friends so you show your social side
  • Wearing clothes that fit you well in every photo
  • Happy photos that express your personality

When you dial in your written and visual communication, online dating becomes much easier and more effective.

Man Working on Laptop - Online Dating

Best Dating Apps / Online Dating Sites in 2022

Here are the best dating apps and online dating sites for introverts in 2022.

What makes an awesome introvert online dating site?

One that has…

  • Quality potential matches
  • A solid platform

Quality is obviously important for introverts and extroverts alike, and for introverted men even more so.

Quality is uniquely important to introverted men for two reasons:

  • Limited social bandwidth, so not optimal to waste energy on low quality.
  • Being a man means you’re more often the one initiating, so it’s even more important that you are initiating with quality potential dates to begin with.

There are three categories of online dating sites and apps:

  • Short-form
  • Long-form
  • Values-based


Short-form dating apps are usually used straight from your phone. They have minimal text (no long profiles), and they are usually attached to a Facebook or other social media profile to prevent/lessen fake profiles.

Here are the short-form dating apps we recommend for introverted men.

They’re in order of our clients’ preference, from most to least preferred:


The app: Hinge

What it is: By matching users through mutual friends in their social networks, Hinge creates dating through accountability. It uses your real-life reputation as motivation to encourage honesty and appropriate behavior.

Logistics: No Facebook account required to use this app. You can create a profile with either a phone number or Facebook login, but you must choose one and stick to it to avoid profile confusion. Free, with the option to upgrade to a paid preferred membership.


The app: Bumble

What it is: Great for introverts. The woman always makes the first move, and if she doesn’t say something to a new connection within 24 hours, that connection disappears forever. How’s that for motivation!

Logistics: No Facebook account required to use this app. You can create a profile with either a phone number or Facebook login. This platform no longer requires a phone app; there is a browser-based version called “Bumble Web” with similar functionality. Free, with some optional premium features to enhance your experience, like Bumble Boost, which enables you to see users who have already swiped right on your profile, re-match with expired connections, and extend your matches for an additional 24 hours.

Coffee Meets Bagel

The app: Coffee Meets Bagel (aka CMB)

What it is: A short-form app where each day, each man is given 21 “bagels” or women to choose from. At noon, the women see their “bagels,” or the men who have already liked them.

Logistics: No Facebook account required to use this app. You can create a profile with either a phone number or Facebook login, but you must choose one and stick to it to avoid profile confusion. Free, with the option to purchase beans (in-app currency) or a premium membership to unlock special features, such as Read Receipts, Activity Reports, and Liking in Discover.


The app: Tinder

What it is: Swiping app with a reputation for more casual hook-ups, but actually has seekers of all types and the quality often varies by location. You can upload up to 6 pictures and Tinder will switch them around to what they consider the best one, so that you can see which ones gets the most attention. Left dislike, right like. If you both swipe right on one another a screen will come up for you to message one another.

Logistics: No Facebook account is required to use this app. You can create a profile with either a phone number or Facebook login. Free or paid premium version.


Long-form online dating sites are more traditional and have longer profiles with more text. They’re desktop-centric, though many now have mobile apps.

Here are the long-form dating websites we recommend for introverted men:


The site:

What it is: A site that ‘learns’ who you are based on your profile and uses a matching algorithm to suggest matches. Match holds their own member events including: expert talks, sporting events and socials that you can sign up for.

Logistics: Full accessibility / functionality on the site is not free (i.e. cannot send or receive messages or see matches unless you subscribe). Plans start at $15.99 per month.


The site:

What it is: Long-form dating site that shows potential compatibility or incompatibility with other uses as a percentage. Based on your responses to a series of compatibility questions, OkCupid will show you a percentage rating for each potential match that you score well with. “Liking” someone’s profile is a function that allows you to establish if you’re a good match with someone before you send the initial message.

Logistics: No Facebook account is required to use this app. Free or paid premium version.

Values-based options

Values-based options can either be mobile or desktop-centric. They can center around a community, lifestyle, religion: an established interest or value.

These are the values-based online dating options we recommend for introverted men:


The app: MeetMindful

What it is: MeetMindful is the first and best dating site devoted to the mindful lifestyle, created by and for people who are into health, well-being, and mindfulness. So if you’re the kind of guy who’s into health/yoga/meditation, this app is definitely for you.

Logistics: Free or paid premium version.

Christian Mingle

The site: ChristianMingle

What it is: If you’re looking for someone who shares your Christian values, Christian Mingle is the obvious choice. With both an app and a website, it has the largest user pool of any Christian dating app.

Logistics: Free or paid premium version.


The app: JDate

What it is: JDate is the largest dating site for Jewish singles, and one of the first online dating platforms. Find matches through the search function, chat rooms, forums, and tests.

Logistics: Free or paid premium version.


The app: eHarmony

What it is: Online dating site and app with a focus on long-term relationships. eHarmony bases its matching system on its 29 Dimensions® of Compatibility metrics, based on data from its user pool.

Logistics: Free or paid premium version.

The League

The app: The League

What it is: Branded as the most exclusive dating app, users must pass a review period and are screened by education level and profession. Relaunched in 2016, the app now includes a focus on events and community in addition to dating. The League is only active in select cities, but for men who make the cut, it can be a useful way to connect with ambitious professionals.

Logistics: Application must be reviewed and accepted before joining. Free or paid premuim versions available.

You can discover much more about this here.

Man with Iphone Camera - Online Dating

Online Dating Photo Tips from PhotoFeeler

This section of our guide is a guest contribution by Anne Pierce, co-founder/CEO of PhotoFeeler, a tool for getting unbiased feedback on how you’re coming across in photos.

Anne and her team have helped a ton of guys improve their dating profiles by showing them how to present the best version of themselves online. Enjoy the read!

If there’s one thing every man should know about dating apps, it’s that a woman assumes a whole lot about you from a single picture.

Researchers out of Princeton asked people to guess the personalities of strangers in photos.

Later, they found that stranger’s perceptions of different pictures of the same person varied as much as pictures of completely different people.

The most subtle cues in a picture can throw the impression off, convincing a woman to see you as aggressive or threatening, for instance, when you’re actually a kind, thoughtful guy.

Add to this the scientific discovery that we use different parts of our brain when we’re looking at pictures of ourselves (making it impossible to be 100% objective about our own images), and you see just how easy it is to choose photos that give a false impression or simply don’t do you justice.

Having worked on a startup called PhotoFeeler with millions of photo ratings, here’s some of my best research-backed tips for getting dating profile pictures that maximize your attractiveness and multiply your matches.

1. Use Natural Light

According to PhotoFeeler data, natural daylight is one of the key differences between photos of the same person with very low and very high attractiveness ratings.

That is, natural light skyrockets attractiveness by making you look healthy, friendly, and fit.

Artificial light — especially of the fluorescent variety — can be detrimental to your looks.

Not only does it adds extra pounds and years of age by emphasizing the creases in your face, but it tends to cast a sinister, creepy vibe over the whole picture.

To maximize the benefits of natural light, find a window in the daytime (preferably when the sun is on the other side of the building / not in direct view).

It’s best to take pictures directly across from the window rather than from an angle to get even light across the whole face, free of shadows.

2. Distance Yourself from the Camera

Camera Distance Example - Online Dating

According to research out of Caltech, pictures taken two feet away or less are consistently rated as less trustworthy and attractive.

Pictures taken that close-up create a less-than-ideal impression for at least two important reasons:

a. Wide-angle lenses (like those on camera phones) create facial distortion when held this close to your face. This is when your nose or forehead looks a little bigger than it really is, throwing your proportions slightly out of whack.

b. To the viewer, pictures taken very close-up mimic the feeling you get when you’re standing very close to someone. This can be a little disconcerting to women who’ve never met you before, since they’re psychologically being put into an intimate situation with you. As a result, they might think of you as aggressive or predatory.

To avoid this, ask a friend to take your dating profile picture or else use a tripod or selfie stick to get some distance between you and the camera.

3. Beat Awkwardness with this Pose

Awkwardness Example - Online Dating

Ever wonder why you feel so camera shy? A researcher from the Psychology and Human Behavior Department department of USC sums it up this way:

“Photographs really cause us to focus on the gap between the true self and the idealized self.”

As a result of this heightened self-consciousness, many people freeze up and forget how to hold their body naturally.

However, there is one pose that’s been shown to take the edge off your nervousness. Next time you feel awkward in front of the camera, simply try sitting down and holding onto something.

Sitting down makes you feel a little bit less exposed and gives you some norms to fall back on. (e.g. crossing your leg; putting an elbow on the arm of the chair.)

Further, holding something — like a glass, the back of a chair, a bag, or your friend’s shoulder — gives your hands a natural position and also subtly gives your mind something to focus on.

4. Be Wary of Your Facial Expression

Sample Facial Expression Photo - Online Dating

I already mentioned the experiment by Princeton University that found different photos of the same person give impressions as varied as entirely different people.

Volunteers in this study felt pretty certain they could guess the personal qualities of the people in the pictures. But they were wrong.

They were just extrapolating a whole lot from each picture — exaggerating any qualities that they could immediately see while downplaying qualities they couldn’t.

(Smile = super gregarious person; no smile = antisocial person, etc.)

According to PhotoFeeler data, “goofy” facial expressions rate low on attractiveness for this same reason.

When a woman sees a man for the first time and he’s sticking out his tongue, she’s not likely to understand that this is a rare but endearing part of his personality! Rather, she’s likely to conclude he’s kind of a goof all-around.

5. Get Feedback on which Dating Profile Picture is Your Best

Would you believe you tend to favor photos that don’t actually look like you? It’s true! And I’m not talking about preferring photos that show you as more attractive than you really are.

I’m saying you tend to pick photos of yourself that don’t look like you in a completely arbitrary way, thanks to a phenomenon called the mere-exposure effect that makes you prefer your more-familiar mirror image (plus other exacerbating tendencies).

Beyond that, you just can’t see yourself with the objectivity that a stranger does. That’s partly because you have too much information about yourself.

For instance, you know that you’re a stand-up guy. So when we see a picture of yourself, the possibility of looking scary or mean wouldn’t even cross your mind.

The truth is, even if you follow the guidelines above, a second (and third and fourth) opinion is key to having that certainty that you’re looking your best.

For quick and easy photo feedback from women, I hope you’ll give PhotoFeeler a try.

Photofeeler Analysis - Online Dating

And that concludes my best dating pic tips for multiplying your matches on dating apps. Give them a spin and enjoy!

Man Working on Laptop with Dog - Online Dating

How to Write Your Online Dating Profile

How to write an online dating profile to get the attention of awesome women, just your type.

Your dating profile is sending subtle and not-so-subtle signals to the women who see it.

Writing a strong profile for Tinder, Bumble, Hinge, Coffee Meets Bagel, or whatever short-form app you’re on is a cornerstone to successful online dating for introverted men. You can discover much more about this here.

Unedited Original Profile Example

“I make friends easily and am out to see as much of the world as I can. I’m always looking to make you laugh (sometimes at inappropriate times). I’m totally willing to help you shop, and help you coordinate your outfits. I have a weakness for girls with style, and a fashion sense. I can’t walk past a baby without going ‘aww how cute,’ and quickly commencing a conversation with them in baby talk…”

Be fresh and relaxed

Being a breath of fresh air is an awesome thing on a dating app where so many words and concepts are rehashed without original thought or genuineness.

There are a couple of ways in which Mark was cliched and too intense for a first impression.

Use of cliches:

Catchphrases and rehashed sentences like, “I make friends easily,” or “I’m out to see as much of the world as I can,” feels very “partners in crime”-esque (the ultimate online dating cliche).

Instead, consider what you are really wanting to say. What is actually true, before the cliches and tired phrases are inserted?

Look for what is real and raw for you. THAT is what is going to stand out online, not a phrase everyone else is saying.

You don’t have to be overly “original” just for the sake of it, but definitely apply that thoughtfulness that you as an introverted man are attractive.

Too intimate, too soon:

Sure, Mark was trying to be playful and helpful by offering to go shopping with a date, but women are not on dating sites to get help coordinating their outfits from random men.

It’s too intimate of a thing to do on a first or second date. It’s jumping ahead too far and seems overly willing.

Maintain manly strength

Masculinity is part of your attractiveness. While this doesn’t mean brutish or over-the-top, it does mean not using weak/overly-mushy words.

Mark was doing a couple of things that undermined his masculine attractiveness.

Associating with weakness:

Even if it’s playful, framing affinity and affection as weakness communicates too much softness, not enough manly strength.

Overly soft with the baby talk mention:

Babies are very cute, and if she sees you do that, it can be an endearing moment. But in the context of an online dating profile description, it’s too much.

It’s mushy, rather than strong and manly (you don’t have to be overly “macho” but definitely show your masculine side naturally in what you write and how you write it).

So how did we turn this around?

He had another part of his profile about walking through a jungle.

We took that theme and ran with it, incorporating what was true about him from the example above (love of fashion, adventure, and his warmth).

Successful Online Dating Profile Example

Successful profiles tend to be playful, relatable, and subtly sensual.

Here’s how we took this client’s raw materials and edited it into a great Bumble profile:

“I’ve walked in an African Jungle, bopped a hyena on the head, and almost got charged by a rhino. I promise not to cause so much trouble on a date with you. 🙂 Let’s go see Antonio Lopez’s creativity in his Future Funk Fashion exhibit. Or we can do Cider Week. Fall + cider + you = delicious. ”

That very profile won our client too many dates to fit in his calendar.

They were all with awesome women, so he had to start only saying yes to the absolute most appealing ones, just to fit them in!

He was stunned, as he never experienced that before. This profile worked because it reflects HIM. Beautifully, and succinctly.

Analysis of Why It Worked

There are several awesome things happening in this profile…

He’s being playful and sensual:

“I’ve walked barefoot in an African jungle, bopped a hyena on the head, and almost got charged by a rhino.”

Bopping a hyena on the head is quite playful.

You don’t have to have something that extreme, but if you can think of something really fun and entertaining that may have happened once, that might be one fun way to showcase your playfulness.

Walking barefoot is sensual. It is, feels, and sounds that way.

Playful, again:

“I promise not to cause so much trouble on a date with you. :)”

He’s being relatable to the kind of woman he wants to date (into fashion!):

“Let’s go see Antonio Lopez’s creativity in his Future Funk Fashion exhibit.”

This is strategic.

He’s building a bond through interest, and he is specific in his references, which further prove his love of fashion and help build the bond as she may be a Lopez fan as well.

Playful, relatable, sensual all in one sentence

Then he finishes up with playful AND relatable AND sensual:

“Or we can do Cider Week. Fall + cider + you = delicious.”

I love this! It’s an awesome sentence because it hits all the points:

  • His specific reference to Cider Week is relatable.
  • Mentioning cider is sensual (don’t you feel warm and spicy when you read / think of cider?).
  • Adding in “+ you” into is playful and flirtatious.


This whole profile shows his personality without him saying blandly, “I like to travel. I also like fashion and the fall season.”

Now let’s apply this to you with an online dating short-form checklist.

Profile Writing Checklist

Here are a few guidelines to keep in mind as you write or edit your Tinder profile:

  • Is your description positive and pleasant?
  • Is it written in a way that invites connections with potential partners?
  • Does it communicate clearly the type of woman you want to date?
  • Does it “show, not tell” sensual, playful, relatable details?
  • Is it clean of frustration from previous dates (i.e. Saying “Don’t Flake” on your profile after a date flaked on you… )?

PRO TIP: Always keep it positive. There is no reason or excuse to be negative in your profile. If you’d like more help on a positive mindset, check out our Introvert Dating Mindset Guide.

Woman in Bed on Computer - Online Dating

How to Get Responses from Women Online in 2022

How to get responses to your online dating messages while spending less time writing them.

Judging from our online dating survey results, “women not responding” is the chief frustration among guys who are trying to find dates through dating apps.

This applies no matter where you fall on the spectrum of messaging approaches:

Maybe you spend a long time writing a heartfelt, personal message to a woman you’ve found, just to hear nothing back.

Or maybe you’re messaging many women per week using a formula you learned from some guy, only to hear nothing back.

No matter your challenge, this 6-step online dating message structure will be a RELIEF to you and to the women you message.

It will help you write…

  • Faster, so you don’t feel like messaging is a major time investment.
  • More intriguing details, so your message will be more likely to earn a response.
  • Sincerely, which is what quality women look for in an initial online dating message.

So read on to discover how to go from “Inbox empty” to “I can’t keep up with the replies!”

The Vital Step Before You Start Your Message

Say you get a match on your dating app.

Naturally, you click over to view her profile photos.

The moment the profile displays, you’re faced with a choice.

You can…

1. Look at some images and make a determination to proceed then and there.


2. Go on to read her description before making a decision.

Something about this match intrigues you, so you pick option #2 and read her profile.

Congratulations! You’ve avoided a major online dating pitfall.

Too often, guys will make a snap judgement after a couple of photos and send off a bland, poorly-thought-out message.

This leads to nothing but cricket chirps in your inbox, which are adorable but also disheartening.

Reinforce this bad habit too many times and everything you hate about online dating will be multiplied over the long term.

In order for your online dating message to succeed, you must look over her profile first.

Here’s what you’re looking for:

  • Genuine point of commonality.
  • Detail or interest she’s included that you’re genuinely curious about.
  • Virtue or trait you genuinely appreciate (and can therefore compliment).

If you notice one or more of these things in her profile, you’re on your way to a stellar message!

And happily you, her profile description contains oodles of these goodies.

Her name is Gwen. In one of her posted images, she’s in a kayak (one of your passions). She’s your age, likes spicy food (as do you), and has traveled to every continent save Antarctica (but she’s up for it!).

Woman in Kayak - Online Dating

Principles of a Great First Message Online

Before we get into our 6-step online dating message structure, a couple of principles about messaging:

Dating is personal, and it should feel that way.

Here is a note we got from a woman-friend of Introverted Alpha about online dating messages:

“If they send me a message and it doesn’t have something personal in it, I ignore it. And it needs to be way better than: ‘Oh I’m totally into what you’re into’… That’s just cut and paste.”

Makes sense, right?

This means showing you have a genuine connection to something about her.

Good things to discuss include…

  • Something you share in common
  • Appreciation of a unique detail about her that you noticed

Avoid endless back-and-forth.

To avoid endless back-and-forth with no end (date!) in sight, stay date-focused in your messages.

There is no need to dive into details of your days that are too advanced for the level of connection you have at that point (you haven’t even met yet!).

Instead, weave her interests and vibe into a date venue suggestion.

This will make you look (and feel) awesome to her because it shows your…

  • high interest level
  • attention to detail
  • creativity

It also keeps a gentle forward momentum towards an actual date, which will therefore make it more likely that you actually end up meeting!

If you’re going back and forth with her forever, she’s going to lose interest because you’re not being bold. Suggesting a date is not pushy. It’s a normal thing to do with new people you meet on a dating app (!).

So when it feels right, go for the date suggestion to meet in person!

Get her number when it feels natural.

If you get her number “because this stupid app is hard to use” — that isn’t attractive. That is negative and disempowered. It just doesn’t sit right with a quality woman.

Instead, either get her number like this: “Would you like to move our convo to text?” or something that is more positive.

If you end up scheduling a date in the app, that works too.

You can get her number after that point if it feels comfortable.

If you don’t get her number before the first date, that is okay too because the app is essentially like Facebook Messenger or texting… it shows up right on your phone.

You can get her number ON your first date; you don’t have to have it before. Pay attention to what feels natural, and you’ll be good!

(By the way, here’s how to get her number in person.)

It’s constructive feedback, not “rejection.”

It’s not personal if you don’t hear back from a woman you’ve messaged.

The reason why it’s nothing personal is that she doesn’t even know you.

She’s not “rejecting” you; she’s simply not feeling enough resonance to put energy into it (especially when a guy’s message was a cut-and-paste to begin with!).

Distinguish yourself from the other guys out there who don’t handle this well:

If you don’t hear back from a woman, use it as an opportunity to see what you could do better.

Our 6-Part Response-Magnet Message Structure

The winning mindset is to keep things fun, detailed, short, and date-focused.

An effective dating app message stays light, invitational, date-focused, and genuine.

It may sound daunting, but it’s surprisingly easy with our proven 6-step message structure.

Here are the steps, no matter if you’re using Bumble, Tinder, OkCupid, Hinge, Coffee Meets Bagel, or any other dating app.

The best, most natural way to do this in 2022 is to start with the first 3 steps and then do the second 3 after a rapport is built. You can follow the organic flow of the conversation while also leading calmly and purposefully to the date.

Here are all the 6 steps together

  1. Awesome X.
  2. You seem Y.
  3. I like that because Z.

Then, once you’ve developed a conversation of two to three back-and-forth’s, say…

  1. I’d love to take you to ___.
  2. I think you’d enjoy ____.
  3. Would you like that?

Notice how it all builds on a specific profile detail and develops from there.

It’s respectful and bold to acknowledge what you like about her, and being so specific and personalized opens all kinds of options for her response.

From there, you’re into a conversation, which is great!

These days, it’s common for conversations to go on for a bit before a date is set up. Just be sure to keep leading it gently towards the date while you go.

This way, you won’t each get frustrated with endless back-and-forth going nowhere.

IT IS NOT HER JOB TO LEAD. It is your job.


So if you’re complaining about a bunch of dead-end conversations, it’s because either you’ve…

  • (a) not established enough of a connection for her to see you,
  • (b) not explicitly led towards a date, or
  • (c) misread her as someone who would follow through, when in fact she’s not likely to follow through at all.

Here’s what to do about each case, (a), (b), or (c):

  • (a) work on Steps 1-3 above.
  • (b) work on Steps 4-6.
  • (c) analyze her profile and first messages to you for early warning signs (they’re there if you look with an open and analytical mind!)

Now, let’s apply this to Gwen.

If you’re on the bolder side, go for sending all 6 steps at once, although it’s feeling more and more natural online to just send one small sentence at a time.

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