30 Days Mastering Tinder

Welcome to Bailey’s Magical Lifestyle Blog~~

Where to begin? One night in the waning days of summer while my roommate was out having sex with a mutual friend’s love interest, a thought struck me. What are the best opening lines on Tinder? How can you find out? Who can you trust to get the answer? That is where I come in.

For the next thirty days I will document each day on Tinder as I fine tune my craft. Will I, perhaps, find love? (No, no I will not)

I will choose one “Match” from each day to test my approach on making first introductions.

P.s. Each lady matched with were later asked for permission and informed that their conversations will by shared on my blog.

Day 1:

I have created my Tinder portfolio. Decked out with a gloomy photo that makes me look sad and creepy as hell, I started my journey in this modern bar scene nightmare. I left my bio short and sweet, “Call me Ishmael” (Why you ask? Whale, because of the puns, baby.) During this time I was working as a Sales Representative at a Wine and Spirits distributing company, it was an awesome gig that kept me busy and entertained; I drove around selling alcohol. Could I complain?

After a few minutes of swiping, (Okay, maybe it was an hour or two.) I got my first match.

Chloe. Already my heart skips at the sound of her name! Could this be love? You can tell this is a woman of class, of such elegance that the approach must be wonderful. We had only one mutual friend in common but our friend was a woman that I had been on several dates with so I knew a lot about her. Our Mutual Friend came from a very wealthy family and only hung out with super upper class citizens, so I could take a chance on Chloe having a wealthy family. By the body language in her Tinder Profile I could also assume that she had wit and sass beyond measure. This was my opening line:

I chose this opening in hopes that being intellectual and witty will get me a response. Now the waiting game!

Day 2:

No response from Chloe. Will I spend the rest of my life alone? (Bro, she could just be busy.) Not getting a message back got me a little discouraged, but how do you get to the Opry? Practice. Spending the evening swiping, with a bottle of Larchago Crianza to please my thirst, I stumbled upon this wonderful Match.

Thinking that maybe my downfall with Chloe was writing to soon I decided to wait a little while before I approached Hannah. (Beautiful though she may be)

As I waited to introduce myself to Hannah I decided to write to another Match from the night before.

Her name was Carley. Her photo asked as many questions as it answered. Why was she in a bathtub? How do her eyes speak such danger while promising pleasure you have never known? She also reminded me of Zelda Fitzgerald, a major turn on for me, which I promptly told her.

I wanted to try the weird quirky opening line once more. (I have a good feeling about this one)

Day 3:

Yeah, my good feeling didn’t play out the way I hoped. Forcing my mind to not linger on this crushing defeat I wrote to Hannah. Feeling that 16 hours of waiting was perfect; I chose to turn the quirky-ness way down on my opening, but keep the intellectual feeling present. Best move ever!

In just 26 minutes I got a response, and it was a wonderful response! You can immediately tell that Hannah is sharp as a tack with an incredible sense of humor. (Two of my favorite qualities in women) I can’t prove without running more tests if turning the quirky-ness down was responsible for the fast response or maybe Hannah just happened to check her phone sooner then the rest. At only Day 3, we still have much to learn. After finally getting a response, it is time to start working on getting a date set. Thinking of just starting small, getting a cup of coffee, I began the dangerous dance of a conversation. One foul slip up can cost us all that we worked for. After analyzing the situation I decided I will propose a meet up on the third message. Time to test lucky number three!

As my sales manager always says, start with an exclamation to get their attention, ask a question to gain their trust, and make a statement to earn their respect. I hesitated with adding the “in the near future” it might make me look like someone in a hurry, which will only come off as creepy over Tinder. Once again falling back on my sales experience I know that if you don’t propose a time statement then your question can get lost in limbo. Plus using the word “near” adds a sense of urgency. Will my theory hold? Let’s find out!

Day 4:

Got a response from Hannah. It wasn’t a no…

At least she noticed my smoothness. It looks like this is going to take a little more work then originally thought. Was suggesting a meet up on the third message to soon? Due to the fact she didn’t say no, I gathered my remaining moral and charged forward! Feeling that pushing the “Meet Up” in the fourth message would have felt weird and desperate; I decided to wait until the fifth message to get back on target. My unwillingness to change the subject could scare her off but I felt for the sake of this Blog I must power forward. Time to test if being a little assertive can work in my favor.

Day 5:

Total silence from Hannah. Doing some research on Tinder profile photos, the best way to increase your Match capabilities is to follow these steps:

For men:

1. Look into the camera. It is best if you are looking up to the camera and a little to the right.

2. Smile, but don’t show any teeth. (Umm, okay?)

3. I felt like this would go without saying, make sure it is just you in the photo. No woman wants to play where’s Waldo while looking at you and all your bros

For women:

1. Don’t look directly at the camera. (I thought that was a little weird)

2. Smile while showing your teeth.

3. Be alone. Finally, something that is not just the opposite of what they tell men to do.

Speaking from my experience with Tinder. Women, please stop using Snapchat filters. You are all beautiful and hiding behind dog ears will only cause me to swipe left. Wanting to test the ideas they laid out I updated my photo.

Now let’s see if it increases my Matches!

Day 6:

Okay, first off can’t we make the “super like” a little harder to swipe? I swear to God, if I accidentally “super like” one more person I will lose my shit.

The photo worked well. Noticed a major boost in matches. I have been doing mass introductions with the “Hey! So fill me in, what are your dreams and aspirations?” opening, so far 100% success rate. Still testing different approaches on finalizing a meet up. Let’s examine the encounter below.

Jessie is a beautiful young lady. She has such stunning eyes with a touch of daring splashed into her gaze. Our conversation went as followed:

Channeling my inner Gaston I went with a compliment right out of the gate. I received no acknowledgement for my effort. She responded though so I buckled. I count this as a failure on my behalf. A much better response would have been, “You don’t think you relate to the modeling career?” keeping the focus on my flirting but giving her an option to talk about herself would have been a much better tactic then retreating into small talk. Gaston would have been disappointed.

Day 7:

Dear Reader, if you haven’t changed your Tinder profile pic, do it! My Matches have tripled. I am putting that test to bed. Major success! Change your photo!

That is all.

Day 8:

Today my “Hey! So fill me in, what are your dreams and aspirations?” opening took a hit. I sent out mass introductions and I didn’t get a single response…

Fearing that maybe my line is a little stale I went back to the drawing board. Due to the success at first, I wanted to look at the pros and cons of what I was working with.

Opening in question: “Hey! So fill me in, what are your dreams and aspirations?”


Threat level is low. You can use this line and never come off as a creep.

Intellectual and relaxed. Shows that you can have an adult conversation while not coming off as condescending.

An instant conversation starter. Asking someone what their dreams and aspirations are is a great way to get them talking while being polite. It being an open-ended question is also a plus.

Simple and straightforward.


Not very exciting. With the insane amount of bros on Tinder shouting out the first thing that comes to their mind, your more “adult” opening can get lost in the shuffle.

Takes some thought to answer. You would be surprised at how much a “Damn girl u b lookn fine” will work, a simple “Hey thx” is a lot easier to type out compared to “Looking to get my astrophysics degree at the University of California in Santa Cruz.”

Doesn’t compliment your match. Whether you mention something from their photo or talk about something in their bio, people like to be complimented.

Simple and straightforward. (Yes, it made both lists)

Rating 3.5 out of 5

All in all I would say it is a good opening. Can break the ice if you have no other options or just not sure what to say.

On our quest for a 100% success rate we are far from over.

Focusing on keeping the pros while getting rid of the cons, I put my mind at work.

Day 9:

After a good night of rest I came up with an opening. Wanting to test it out on a difficult match, I decided on Sophie.

Sophie was a tough match to read. Shy, guarded, and strong my opening will need to feel truly unique in order to get her attention. Unfortunately, a truly unique opening is hard to mass produce. Wanting to test out a more bro-ish opening I went with the following.

Is it perfect? Probably not. But keeping the pros from the last opening and going to the extremes on the cons we have a way to work towards the middle and find the Ultimate Tinder Opening, which is crucial in our journey of becoming a Master of Tinder.

Day 10:

Just as I feared our last opening was a total failure. The conflict between bro-ship and intellectual-hood fought in a glorious battle, who won? No one.

The flow of the opening was lost and it quickly became a problem. Needing to gain my direction I took to the drawing board. Starting from scratch I came up with a line I have the highest hopes for! Now to find the perfect match to test it on…

P.s. What the hell is with “running out of likes”!? I feel cheated.

Day 11:

As if out of a glorious dream, my line came to me. Doing a lot of research on women’s psychology I have found studies stating that women are 40% more likely to respond to a question if it is about food. I shit you not.

Using that knowledge I have came up with the following:

If you put all my accomplishments in a list and ordered them from worst to greatest I would put this opening line on top of the list. Simple, elegant, funny, and witty, this opening has it all. Now let’s take a look at Amber.

Pretty eyes and a beautiful smile. I went with the second photo because someone hasn’t read Bailey’s Magical Lifestyle Blog *shame* and used a group photo for her first picture, as if trying to hid her natural beauty. Like I keep saying, all of you women are beautiful! Own that shit, girl!

Day 12:

The new opening is off to a tremendous start! I feel like I have struck gold. I chose to talk about Amber because of the difficulty in getting a conversation started with her. Just read the following below.

She gives me nothing! One word responses, no sign of interest, but due to the amazingness of our opening we can turn this around. Check it.

See what I did there? Turned our opening into a joke and got her talking. Now we have earned her trust and the power to take the conversation anywhere we want. (Also did some harmless flirting and kept the conversation jovial.) The versatility of this opening is what makes it so amazing.


To get back on track of Mastering the “Meet Up”.

With Hannah I tried a very pushy tactic and that didn’t go very well. (I was a young man back then, I didn’t know better!) Taking a slower approach I went with a more casual question banking on her giving me a chance to ask for a meet up in her response.

I was really torn on including the word “like” in my question. I chose to leave it because it gives Amber more control over which way she wants to steer the conversation. (But wait, I thought we wanted to gain control?) This far into our conversation it is time to see where Amber stands, and how do you find out which decision your enemy will make in war? Give them the illusion of control.

Day 13:

Bad news. I had to bail on Amber. Look at her response…

She is still wanting to talk about her dog! I gave her a chance to talk about anything in the world and she keeps the subject on her pet! Seriously women, a man can only go through so much! If you are using a dating app and want to socialize with other human beings, when they give you a chance to talk about anything interesting or exciting in your LIFE; don’t talk about your dog.

On that note I quickly responded with a polite, “Well it was a lovely day for it!” and then got the hell out of Dodge.

In the mean time I have started up a lovely conversation with a young lady by the name of Corrie.

Dark, mysterious, and alluring, I would be proud to land a meet up with her. Setting my sights high I sent in our faithful opening and got a quick response back. Using the Bailey’s Magical Three Message Approach (Patent Pending) our conversation took off.

Ahhh, the joy of success! Off to a great start, now let’s begin working our way towards landing a date.

Day 14:

Today was the most uneventful day ever. Stay posted.

Day 15:

What a difference a day makes! Managed to land a closing line today. Went out a limb and went with a more quirky closer.

Will it work? Honestly, I am not sure. Our conversation has gone well so far but she gave me nothing (literally) to work with. Feeling pretty confident that the approach I took with the closer was the best option we had. I went with my instinct and did the best I could, can you blame a man?

Day 16:

Damn Corrie can dodge a question!

I am beginning to think that Snapchat is where all the “planning” takes place. Could it be that we have been doing this all wrong? Should we try getting a phone number or Snap account before working on a “meet up”? Only one way to find out. This was my response to Corrie.

I chose to keep the topic of the “question” in play for fear that if we didn’t her deflection would have worked. Now, to master our conversation in Snapchat. (Who would have thought we would be crossing platforms??)

Day 17:

Still waiting on an “acceptance” from Corrie on Snapchat. I started talking to another young lady by the name of Lily.

Looking directly into the camera (I told you I thought it was weird that they said not to do that.) while flashing her pearly whites, I was hooked. This time rather then working on a “meet up” right off the bat, I will attempt to get her number, then work on the “meet up”. Going forth I went with our handing dandy opening line:

Waiting for her response I put my mind to work on a strategy for getting her number.

Day 18:

Transferring over to Snapchat has been rough. I feel like a young lad who has just taken his first steps into a new world. (Maybe that is a little dramatic.) Not sure how to make an introduction I went with the following.

I panicked! Should I have sent a photo first? Would a simple “Hey” have worked better? This got a lot more complicated then I originally thought. When we started our Tinder journey I never would have thought we would end up so far from home. I went with a quirky/funny opening in hopes that I could get a chuckle out of her that would translate into a response. I didn’t take into consideration that all of our history went out the window now that we jumped platforms. I feel we would have had better success if we just started fresh. Also, it might of told her I took a screenshot of our conversation before she even got a chance to read it, I have a feeling that won’t work in my favor.

Day 19:

Spending hours looking for a solution on how to take snapshots of Snapchat conversations without alerting the other user came to no avail. I then was left with two options, don’t take a screenshot and just leave you all in the dark, or take a screenshot and hope Corrie won’t notice. I went with the latter; she noticed.

With just a few options left, I decided to come up with a crafty story that she might believe. (All this because I didn’t want to leave you in the dark. See how much I care?) I am really not sure if I will ever be able to repair our relationship with Corrie. She could have been the “one”.

From now on I will swear off of Snapchat. I will go for a phone number or an actual “meet up”, nothing less.

Reading more about different tactics to use on Tinder I found a new skill to test. The theory is that if you get no response from you first opener, you can send a second message. This is known as the Follow Up Technique.

Not getting a response from Lily, I thought it would be the perfect chance to begin our practice.

Yet one more skill for us to learn before we become a Master of Tinder.

Day 20:

Yet another uneventful day. No response from Lily.

Day 21:

Having two days in a row with no matches I decided to read into our new dilemma. Based on the info I could find it seems that Tinder puts the most “active” users at the front of your feed; this means that after awhile, you end up swiping on people that haven’t used Tinder in a long time.

Is this the world telling me I kinda over did it?

Needless to say I am embarrassed that I had to include my dysfunction in my blog. Please forgive me.

Day 22:

We’re back in business, baby! Few new matches and a response from Lily. Check it:

I love that she responded with humor. Not wanting to lose the feel of our conversation, this was my response.

For those of you outside of the states or reading this in the future, on August 21, 2017 we had a solar eclipse that spread across the U.S.A. Living in Nashville we were all in the path of “totality”, it became a major event. Hence my remark about it in my response.


I kept the quirky/witty style in my response due to the nature of our conversation. Depending on her response I hope to try closing the deal with the next message. Stay posted.

Day 23:

While we wait for a response from Lily I have sent out an opening to another match. Her name is Victoria.

Dearest Victoria, my heart melts at the perfection of your profile picture. (Even though it goes against everything that is recommended for a woman’s Tinder pics. Seriously, what the hell is with the tea kettle?) Something about Victoria speaks volumes to me. Could it be love? Let’s find out.

Went with Old Faithful for our opening. If we get no response in a day or so, we can fall back on our Follow Up Technique. At Day 23 our power, knowledge, and wisdom has grown.

Day 24:

Got a reply from Victoria. Responded back with.. yada, yada.. you know the drill.

One thing we know at this point, if you want to surprise a lady with breakfast in bed, bring waffles instead of pancakes.

Day 25:

99 Matches, and haven’t meet up with one. If you’re having Tinder problems, well shit, we all are.

Day 26:

I almost don’t believe it, folks! After years of constant study and perseverance we have found the chosen one.

Jordan. Playful, innocent, (In all the good ways. Don’t judge.) and impressionable (Again. Don’t judge.) Jordan has it all. But what makes her the chosen one? I am glad you asked.

Jordan chose pancakes! I didn’t think it was possible. I am so honored that I would be the one who discovered this unicorn among women. Knowing I had to act fast on this one I cut straight to the chase.

Some of you might have guessed where I plan to take this conversation, others will need to wait and see. One thing is for certain, I have big plans for this unicorn.


By using the Follow Up Technique I got a response from Victoria.

Sounds kinda fishy, I will need to keep an eye on this.

Day 27:

Nailed a closer with Jordan. Pretty proud of this one.

I know, I know, it’s a long shot and even longer winded. But I knew I needed to take a chance. About five minutes after I sent it I received this.

So, it started a little weird. (Who sends a first text with, “What are you up to?”?) Now that we crossed platforms I knew we couldn’t pick up where we left off on Tinder, (Remember Corrie?) so I started a little small talk.

And that was the end of my small talk. I’m sorry, I love you guys but I am not going to drive an hour out of town to meet up with her. I did tell her if she is ever in Nashville to shoot me a text, and she agreed. If she reaches back to me I will come back to inform you all.

Day 28:

Today I sent out an opening to Samantha.

I know I say this a lot, but she is just wonderful. She has such an inviting smile and incredible eyes. If we get no response by tomorrow we can resort to the Follow Up Technique. It is only a matter of time before we start our inevitable conversation. (Mwahaha!!)

Day 29:

One day left with nothing to report. Sad day.

Day 30:

Well folks, it is Day 30.

Total Matches: 101

It is tough to describe how this experiment went. Looking back on when I first started Tinder I can see major improvement on my Tinder Game. I definitely learned a lot and no longer feel like a beginner; do I feel like I have Mastered Tinder? No, I don’t. But, as Malcolm Gladwell says, mastery takes 10,000 hours of practice. I roughly put in two hours of practice a day, so after thirty days that puts me around sixty hours total. Unfortunately, the next 9,940 hours I must walk alone…

Stay tuned for my 8 Favorite Experiences of this experiment. (Here)

As always thanks for the support and comments! I look forward to next month’s 30 Day Challenge. (30 Bars in 30 Days)

Bailey’s Magical Lifestyle Blog~~


19 thoughts on “30 Days Mastering Tinder

  1. Bah, I came here too soon. I should’ve waited until the 30 days were over so I could binge-read this Netflix-style. I’m excited to read how the test of the 30-days go.

    Liked by 1 person

    1. To be honest, that was a fear of mine when I started this experiment! Hopefully, I will just die alone to save me from needing to show “The One” my Blog. Fingers crossed! šŸ¤žšŸ¤ž

      Liked by 1 person

  2. I found this fascinating, as I am not from the online dating generation. (I’m 65!)
    We actually had to meet people, face to face, leaving our houses to try and find them in public places. :).
    I was surprised you wouldn’t drive an hour, to meet Jordan. At your age, I would have.
    Thanks for following my blog, which is much appreciated.
    Best wishes, Pete.

    Liked by 2 people

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