The 8 Step Guide to Online Dating for Men

You are entering (or re-entering) the dating world. Online dating is a very good way to meet the right person for you. You can use, e-Harmony (for Christians), Tinder, Bumble, and so many more.  Here we have tried to compile our quick start for men. A few things to understand: this guide is intended to give you the best possible chance to have a relationship with a woman. Some suggestions you might take issue with as they may feel manipulative or deceptive. I think you should understand what works best and then decide from there what works for you. 

The best advice I ever received was to try more than one type of online dating. For example, try (traditional)  and Tinder as you will get different potential matches and you can express yourself in different ways. 

1. Pictures are everything

  • Your pictures are the most important part of your online profile. The words you write, unless they are exceptional, will blur together with everyone else’s. 

Statistics show 90% of a decision is made on the pictures you post. So if they are so important, then what should you post?

  • For guys you should have at least one picture where you are NOT smiling and NOT looking at the camera. Be doing something interesting. Have someone else take the picture. 
  • A picture of you with an animal tends to work well.
  • Humor – if you can show that you have a great sense of humor it cuts through all of the concerns. Women want to be someone that is fun. 
  • If you are insecure about your weight or how you look don’t hide your size or looks but definitely try to highlight your best features. That is what makes you unique. 
  • If you travel, show yourself traveling. If you like staying close to home then by all means show what you like to do close to home.
What SHOULDN’T you have in your pictures?
  • Pictures of you in your favorite costume
  • Dick pics or anything suggesting it.

2. Words are something

What you write in your profile isn’t as important as the pictures but you can easily turn off a potential mate with your words. Here are some suggestions:

  • Use good grammar and spell everything correctly.
  • Be open to new opportunities. Tell people what you would like to learn.
  • Be funny!!!! If you show any anger or resentment, or anything else negtative in your profile women will skip past you faster than a balloon in a fire.
  • If you have kids at home then you need to be upfront about it.
  • If you have something that you feel strongly about then make sure you write it down. Political affilliation? Smoker? Religious?
  • Ask a question of them. 

What SHOULDN’T  you write?

  • You don’t have to say what you are looking for. You may or may not know.
  • If you are just looking for sex, relax. Many women want sex as well but leave that out of the profile. It’s a turn off as an opening line most of the time.

3. You found a match. Now what?

Congratulations! Usually there is a bit of messaging back and forth. I’ve found that being fun and witty matters early on. With messaging that is easier as you can take the time to compose your response. Studies have shown that you will move to the next level if you don’t message back immediately. How long do you wait? More than a few seconds, less than a day. Also, the more messages you have exchanged the more quickly you should respond. Playing hard to get makes a potential mate feel like they is actually a connection between you. 

Don’t EVER say “What’s up?” as your first message. Take the time to be at least a little creative. Be personal. Be FUNNY!

I have found that timing is everything of when to ask to meet or exchange phone numbers. If you are seeing interest from the match then say something like, “I don’t like messaging back and forth, it’s hard to get to know you. Can we talk on the phone or meet sometime?”  From this simple question you find out how interested she is and what her comfort level is. 

4. The first conversation

The first conversation, assuming she gave you her number is incredibly important.

Rule #1, if you get her phone number DON’T SEND A DICK PIC!. I have heard from so many women that the first message is a picture they don’t want. I don’t care if you have an amazing body or not. You will likely waste the time and effort you have spent with this woman. 

Be confident, listen, ASK QUESTIONS. Look for common interests. These don’t have to be deep questions and they don’t have to be surface level either. You are trying to figure out if you two are a match. If you are just looking for sex then you can gently lead the conversation that way. One woman asked me if I like kissing. It was a simple yet rather interesting question. That certainly led to more questions but it let me know what was important to her.

If it seems like a good fit, ask if she would like to meet. If it isn’t a good fit then let her know. It’s okay to just say “This doesn’t feel like a good match to me and I wish you well.”

5. The first meeting

OK, now it getting real. Meeting someone for the first time? Where do you meet? What do you do?

The first woman I went on a date with after my ex moved out was amazing. She was gorgeous, smart, and extremely sexy. She gave me lots of advice and now I share it with you:

  • If you are looking for sex don’t go for coffee. It isn’t romantic. Go to a dark, distinctive bar. Be original. 
  • If drinks work out then walk somewhere close for dinner. Dinner should also have a cozy atmosphere. McDonalds is not sexy, neither is Chili’s. 

More tips I have learned:

  • Do something unique and something where you have an opportunity to touch each other. It has to be relatively public. Dancing, a haunted house, painting workshop. 
  • Give both of you an “out”. Start small: drinks first or a short walk.
  • Let her know before you meet that you are giving her an “out” such as saying, “Let’s meet for a drink at this place and if it goes well then we can go dancing afterwards.” She will know that you are confident and she doesn’t have to fake it. 
  • If it doesn’t feel right it is okay to say that at the end of the date or follow up with a message afterwards.
  • If it DOES feel right then it is perfectly okay to say, “I’d like to see you again. What do you think about that?”. If she says, “Yes, that would be great” then rock on! If not, then politely end the date. 
  • If she agreed to a second date then ASK if you can kiss her. In my experience that kiss is an indication of how outgoing or reserved she is. Pay attention! 

6. The second date

In my experience when using Tinder the second date is the deciding date about what kind of relationship you are going to have. The first date was to see if you are compatible. Both of your guards are up.  The second date has some level of mutual interest and acceptance of each other. This date has to be awesome. Awesome doesn’t mean expensive. Dancing, a comedy club, a live band. Painting at a workshop, TedX event, a hike, frisbee golf, a corn maze, pool, serve at a soup kitchen, a picnic on a lake, etc. The goal is to do something that is truly enjoyable to you and her. I recently had one at a “Blind cafe” where we ate completely in the dark. Our vision was gone so all of our other senses were lit up trying to eat in the dark. 

So how do you behave/talk? We all try to look our best early on when we are interested in someone. We are selling ourselves. The trick is to not oversell yourself. Try to show her the person you really are. If you hide from her its not a very good foundation for a relationship. So be vulnerable. Showing her you aren’t perfect goes a long way with anyone. If you have anger towards your ex then 1) you need to deal with that 2) let her know if she asks. Ask her more about her and who she is. Listen. 

7. Don't be afraid to end it

Ending relationships peacefully may be harder than getting into one. However, if you are truly seeing the relationship is a good fit then you need to end it. Not next week or if you can get them to change. Just end it. It is perfectly okay to say “This relationship doesn’t seem right to me. Here is where I am at: ” You finish that sentence with why it didn’t work for you. Not things that she did or didn’t do. She was being who she is. You have the right to say why it wasn’t what YOU needed and there is a big difference between them.

More information:

This article is compiled from multiple sources as well as my own experiences. If you want to know more details or are curious about really understanding modern dating I recommend the book: Modern Romance by Azis Ansari. Yes, the comedian. He wrote the book after struggling to understand the dating landscape. It is not a comedy book. It is a researched and deeply insightful book about how dating works these days. 


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