8 Lessons from 8 Months of Online Dating


A long time ago my dad taught me to always eat my fries first because otherwise your girl will steal them.

My uncle gave his own sage advice. “For the first date, you want to take her out for soda pops. And then for the second date, you take her out for ice creams (sic) And if the dates don’t go well, then you’re just out the cost of the soda pops.”


I went in trying to find a girlfriend. The hook up culture doesn’t really interest me.


I used Okcupid and Tinder. I bailed on Tinder after a while because it required more work (lots of swiping for few matches) and had low quality dates. I almost never went past the first date with the girl. I also like Okcupid more because you get substantially more information about the girl, and you can search by filters.


I had a few rules when I started.

No vegetarians
No feminists
No single moms
No smokers
No one under age 20

I ended up adding some new rules

If the girl sounds dumb online, she’ll be WAY dumber in person
Never help a girlfriend move


Meet up in person as soon as possible
Make the first date cheap/free
Go for a kiss on the first date, if it’s meeting for coffee/ice cream and it’s short, the second date is the make or break point

If you’re at a restaurant, and you order fries, observe what the lady does

A) if she orders her own fries, great
B) if she doesn’t want your fries, great
C) if she ASKS if she can have a fry, fine, I’ll give it to her, not a problem
D) if she takes fries WITHOUT ASKING that’s a red flag

You’re going to go on a lot of first dates. It’s important to find one that works well for you. I’m not a bar guy, but it works for other guys. I liked either going to a park or ice cream. Ice cream is a good default date for me. It’s easy to go on a walk after if it’s going well, or you can just be done.

Coffee is another option. I don’t drink coffee, but I’d order hot chocolate.  That’s under $5 a date, plus however you value your time. Making the first date short is not a bad idea. It’s courtesy to give them at least, say, 20 minutes if you want to bail, but 40-60 minutes is plenty to get an impression of if you want to continue. If the date is going well, it’s fine to keep it going. Some guys will recommend “leave her wanting more.” I’m not big on playing games or manipulation. With me it’s pretty much what you see is what you get.

On to the lessons:

1) You have to have an interesting life to be interesting to girls

I find so many people with boring lives. They have no ambition. Work some job they probably hate, come home and play video games or watch Netflix, and repeat. Maybe on the weekends they’ll go out and drink, or hang out with friends, which means sitting around drinking.

Maybe your life isn’t boring. Maybe you have some cool hobby. That’s great, show it off in your profile, and you’ll attract people who think it’s cool. I had some very fun dates – archery, rock climbing, I even bought a fishing license for one date.

Fill out your damn profile. I saw so many profiles that said “I like to laugh, have fun, hang out with my friends, and travel.” “Maybe I care about some sports team.” “This is my job” “This is my pet, if he doesn’t like you I don’t like you.”

That’s very generic. The girl I ended up dating wrote an extensive background about who she is. I did the same. This leads to my next point:

2) Put the effort in

I put a lot of time in. I wrote and re-wrote my profile. I had to go take pictures, since I didn’t have the right kinds on Facebook. You should show your face, your body, and your personality. Far away pictures showing you at some landmark, mirror selfies, you and tons of friends, those don’t help me figure out who you are.

The person is going to find out what you look like the first time you meet. Sometimes the girl would have a compelling profile, but I had no idea how she actually looked. I gave a lot of girls chances, and I always got burned. If you don’t know what she looks like, move on. If the profile tells you nothing, what do you think you’re going to talk about?

3) Women love to talk about dating

I also found online dating makes small talk significantly more interesting. Normally I have difficulty successfully getting to deeper levels of conversation. I got a lot of feedback and encouragement. Women also have single friends and love to play matchmaker.

4) It’s a numbers game.

Guys have to message/match/swipe a ton to get any kind of response from women. Girls above a certain threshold will have their inboxes flooded. I asked girls about this, and a good percentage of the messages are straight propositions for sex or nude pictures. I didn’t ask if they complied.

*Note for both guys and girls: If you’re going to send the first message, say something more than “Hey =)”

I always tried to meet the girl in person as soon as possible. My goal was to find a girlfriend, not make friends. If the girl is dancing around meeting up in person, she’s wasting your time. You need to find out if she’s a good match for you or not as fast as possible.

Step 1) Read her profile. Don’t just look at the pictures
Step 2) If you like her, send her a message, if not, look at another profile
Step 3) if the exchange goes well, ask her out, if not, look at another profile
You need to decide your own pace, but if you have at least one date set up a week, that’s a good baseline.

The numbers game means you by necessity need to date more than one woman at a time. It’s not mean, it’s reality. It would take far too long to message a girl, wait for her to respond, message her a few times, ask her out, see how that date goes, and then have to start over if it doesn’t go well or she doesn’t click with you.

The numbers game can also work to your advantage. It allows you to experiment. There’s always another girl. You can see what kind of messages get the best response. You can try wild hail Mary’s. That aspect made Tinder a bit more fun for me.

And even if a date goes bad, you might be an entertaining story to some of that girl’s friends at worst. Most of the dates I had where we didn’t hit it off, I just don’t remember much of them. So it’s likely that it just won’t matter. And the next girl doesn’t have to know.

5) The best way to get over a girl is to find another one

You’re going to find multiple profiles of someone who seems just absolutely perfect for you. You’ll write a beautiful, heartfelt message, be so excited, and get no response. Keep in mind that it doesn’t matter how perfect they appear on paper if you can’t meet them in person.

Another thing that can happen, you’re messaging a girl, and then she suddenly drops off the face of the planet. No response, maybe even her account shuts down. You’re never going to learn the reason. That’s a frustrating reality.

Another frustration is that you’ll never get an honest answer of why a girl doesn’t like you, or breaks up with you. So don’t ask. She may not even consciously know. But she won’t want to hurt your feelings. So it’s on you to try to be aware of what you’re doing, see if you recognize a pattern if it’s a perpetual problem.

Last summer I was in a wedding. I fell hard for a girl that I knew I wanted to marry. We hit it off that night, and went out again the next week. She was supposed to come visit me after I got my tonsils out, but instead I got a text that she was getting back together with her ex-boyfriend. That was probably the hardest break up to get over. I felt cheated. I didn’t “really” get my shot with her. It took at least a month to not feel sad, and the pain kept creeping up occasionally even months later. All for a girl I spent a total of 2 days with.

It’s so interesting to me that I honestly don’t care about a girl once I find another one. New relationships are exciting, and I think my mind just discards what’s not important —> the girl that dumped me.

6) It only takes one to make it all worth it

I wanted to take a break from online dating. When I started this article, I was ready to be single. But the day I was going to freeze my account, I got a message from a girl. I decided to go on one last date.

She did message me “Hey =)” so I decided to make her develop the conversation. She did a good job, and I wanted to meet her ASAP, because of the rule, plus it was close to Christmas. I didn’t want to lose momentum.

She messaged me on Wednesday, and that Friday night we met for Ice cream. I got there a bit early. The store was pretty empty so the guy behind the counter kept giving me weird looks. I told him I was waiting for someone.

She walked in about 10 minutes late. She said “Hi” and hugged me. She told me how she hates getting gummy bears in her ice cream, but she ordered them anyway. When she went to pay, her card was declined. She ran to the car to get some money. I paid for her ice cream and sat down. She came back, went to the cashier, he told her what happened, and then she spilled her change all over the floor. I helped her pick it up.

Then we finally got to sit and talk. She was flustered, but still in a good mood. Also, she paid me for the ice cream, which was a huge green flag. The conversation went well, and I offered to drive her to her car. We stayed in my car for quite a while talking. She was paranoid about the employees walking out the back of the building.

I told her she needed a distraction, pulled her in and kissed her.

She was laying on my lap, looking up at me. “You’re really pretty. I’m looking at your nose hairs and all I can think is how pretty you are.”

I didn’t know what to say. I looked like a stereotypical nerd growing up, so I’m not used to being considered good looking.

That night she sent me a message asking me out for lunch the next day. She offered to pay.

We kept going out, and talking on Skype pretty much every night. I went to her parent’s house for New Year’s. I wrote her a handwritten letter asking her to be my girlfriend.

We’ve been dating for about 3 months now. It sounds like a cliché thing, right when a person is about to give up on dating, they find someone special. It happened to me at college, I had spent a few months trying to find a girl, and the day I decided to give up, I found her that night at dinner.

I was honestly ready to be single, but being with this girl has improved my life so much.

She’s helped me learn what an adult relationship should be like. She treats me so well; it makes me wonder how I put up with women before. She also helped me significantly purge and upgrade my wardrobe. She also cooks, is happy as a default, and makes me laugh all the time. Sometimes it’s involuntary since she learned I’m ticklish.

7) People will give you crap for online dating

I got called a man-whore so many times. Sometimes it was intended as a compliment. Some people were saying I should meet a girl at the gym, or take a class or something. That’d be a better use of time. It might be. If I was in an acting class or something, I’d know what the girl looks like, and that we had one interest in common. When I’m online, I know for sure she’s looking for a guy, and I get a little broader spectrum of her life.

The criticism didn’t bother me. I knew I was taking steps to create a reality I wanted. People project criticism often because it’s holding a magic mirror up on their own inaction – i.e. all the teasing I get about working out.

*Side note – I saw it was common on profiles to see a girl write something like “no gym pictures, no mirror selfies, if you’re in shape don’t message me, I don’t need that kind of pressure in my life.”
Fitness is a pretty big aspect of my life, but this makes me sad. I had a bunch of girls say something along the lines of “I feel like I’m not good enough for you.” They weren’t just talking about our comparative fitness. Fat acceptance isn’t the answer. Education about health and making it a priority should be.

8) Write down the stories

I wish I could remember specifics about the girl that inspired the rule about dumb girls. She was the first and only date where I wanted to leave the second I saw her. I don’t think anything catastrophic happened on any of the dates I went on. I got turned down for kisses, blown off after the first date, dumped out of nowhere via text, but nothing that made me feel like the world was ending.

I think that was a big key for my success. I wasn’t feeling pressure. “This girl HAS to like me. OMG what did she mean by that? Did I screw up? What if she doesn’t call me back? Was my shirt too ugly?”

I just went out and tried to have a good time. I was pleasantly surprised that I never felt nervous on a date. I’m not a people person.  I’m assuming others have similar experiences. Maybe for the first few dates, you might crash and burn. Once you go on a few dates, you’ll get more comfortable. Meeting women is a skill like anything else. Think about how nervous you were when learning to drive.

My last advice to keep in mind is on a date, keep in mind that the girl ALREADY LIKES YOU. She agreed to show up. She’s hoping for the same thing, that you guys hit it off and have a great night.

And if all this seems like too much anxiety or effort, think about the impact on your life.

“Hey Bill, what’d you do this weekend?”

“I pulled a 48 hour Call of Duty marathon, I got a golden gun from this sick 360 no scope. What about you?”

“I went on a few dates. One girl accidently set the bar on fire when her scarf got too close to a candle, and we ended up being chased through a park by the bouncer. We escaped by hopping in a horse drawn carriage who brought us to this awesome pretzel stand. We’re going out again on Wednesday.”

What kind of life do you want?

Prize at the end of the rainbow

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