Insider Dating Tips from Real Women for Online Messaging


Hello, fellas. I’m back with some feedback and advice for writing those online dating messages. First, a disclaimer, heed the following advice but remember there are no guarantees that every woman you want to respond to you is going to. No pickup artist, or wingman is going to supply you with a 100% effective technique. I’m only giving you material that I’ve gathered from a group of ladies that supplied me with their opinions when I asked them about online dating messages.

Okay, first off you got to realize that everyone deals with rejection. It’s a huge part of dating. Learn to brush it off and keep your spirits high. Like my mama always said, “You are not a gold coin. Not everyone is going to like you.“ If they don’t respond, don’t magnify it and make it personal. Quite honestly, I’ve gotten messages where the guy seems attractive but when I’ve looked at their profile, I realized that they are just not someone I could see myself with. It’s just the way life goes. Just as you are selective of whom you message or which women attract your attention, so are the women. Those women that didn’t respond to your nice messages… I can 100% guarantee that they’ve experienced unrequited love themselves. They’ve been rejected before. We all have. No use in wallowing in self pity. Move on. You are that much closer to finding the right person.


The Do’s And Dont’s of a First Message

Now for the tips on how to write that first message. Use the KISS principle. It’s something I learned in design school and it means, “Keep it simple, stupid”. I don’t really know if the stupid part is necessary… or maybe it is. When we don’t know something, I guess we are all stupid. No one enters the dating world with all the answers, right? My point is, keep it short and sweet.

Think back to when you were a kid on the playground. When you saw another kid that you wanted to play with, you just went up, said, “What’s your name?” and offered them one of your toys or suggested a fun game to play. It was so simple. Now as adults, we’ve made things more difficult for ourselves. We have to deal with fear of rejection and lack of confidence. We’ve put that other person on too high of a pedestal. You might approach women with words such as, “Wow! You’re beautiful!” or “What a gorgeous smile! “ and if those techniques haven’t worked, it’s time to change up some things.

No Worship
First off, don’t use the worship approach. It immediately places you on a different level than her. And that’s an uncomfortable position to start at. Especially for the woman. She wants someone at her level. Someone that exudes confidence. Remember to channel your “playground attitude”. You see someone that piques your interest, and you approach them in a “ Hey, we’ve got something in common. Let’s play!” manner. If they aren’t interested, it’s no biggie.

No Sexy Sauce
Lay off the sexy sauce when you first message a woman. Keep it friendly and casual, not creepy. Leading with comments about her looks can come off as insincere. We know that “ Beautiful eyes!” can be used in hundreds of mass emails.

On a side note, please don’t take this advice as me saying to stop complimenting. All I’m saying is, simmer down on the compliments before you’ve met her. Once you’ve met her and start to get to know her, by all means, we like hearing sincere compliments. It’s always nice to hear nice things from someone we like.

Credit: Adriana Green

Do Read Her Profile
When writing to a woman, start with one or two hints that you read her profile and a simple question to engage her.

Something like…

You’ve got great taste in music! I’m a big fan of The Walkman too. Were you at the show at The Fox last summer?”


Is that Yosemite in your pictures? Where is that waterfall? It looks amazing, I’ve got to find it.”

No Homework Questions
Don’t use any of those what I like to refer to as “homework questions”. These are those generic “icebreaker” questions that I just know someone is doling out to poor guys seeking dating advice. I just see them all too often. These include messages like, “What is your favorite color?” “Tell me about a childhood memory that shaped who you are today? “or “What are three things you’d like to accomplish this year?”.

No Autobiography
Don’t send out lengthy messages that include autobiographical information or your resume. In fact, the less about you, the better. It’s never a good idea to brag. If you are accomplished, you look much better if you don’t lead with that and then the woman is pleasantly surprised by your achievements after she’s gotten to know and like your personality. This goes for your profile too. It’s one thing to mention your career if it’s something you enjoy but when a guy starts to get into all the awards they’ve received or all the times they’ve saved the world, it starts to look like you are showing off. And no one likes a show-off.

In researching for this article I sorted through a bunch of dating messages sent to some women and categorized them based on whether they received responses or were ignored.

Messages That Get a Response:

(Profile mentions that she is allergic to cats.)

How’s it going? I am with you on the cat thang…”

(Profile mentions her fondness of hot sauce.)

I love dousing my pizza with hot sauce!
What is your favorite sauce?
So yeah, it sucks to realize that people are too insular to make connecting in person possible. Alas, here we are.”

(Woman is a creative type.)

Hey, you seem like a really cool person. Forgive me for being forward, but I just thought I’d ask if you would like to grab some coffee with me some time? Maybe even bring some pencils and draw some sweet doodles on paper? Caffeine and creation do go well hand in hand. Have a wonderful night!”

Messages That Are Ignored:

Hello how are you sweetheart? We should go out sometime?”

Hi dollface. You are gorgeous. I would love to talk to you. Message me back! :)”

Hola Hi! ;-)”

u sure u 34? u look 20″

Hello I am that super sweet funny man you are searching for”

You are so sexy! Check out my profile and Q&A’s. Let’s chat.”

I mean wow, just wow!”

You are very beautiful… Wanna talk on the phone?”

Hello. How are you. Interesting name.”

Do You Notice the Differences?

The messages that were responded to are short, casual and customized to the woman’s profile. They don’t state anything sexual or generically complimentary. Of course the woman needs to check out the men’s profiles to see if she has an interest but she can’t disregard these guys on their messages alone. The fact that the messages are short also help the men out in case the woman doesn’t respond. They didn’t devote 30 minutes of their time into a message that doesn’t get a response.

Tips from Courtney

In the messages that didn’t get a response, the commonality is that they are generic pickup lines. Women get those messages all the time. The thing with that is, the guys that are sending them do not stand out. The truth is, those pick up lines are only going to be effective when a woman is naïve, insecure or you just happen to have looks that she can’t resist. If that is what you are looking for, then you’ve got it easier than the rest of us. But if you are looking for someone who is comfortable in her own skin, selective and has heard the same lines too many times to take them seriously, I suggest you don’t take that route.


When You Get a Response

If that woman that you had your eye on does respond, do yourself and her a favor and try to meet in person as soon as possible. Only when you meet face to face, will you know if there is possibility for a love connection. As fun and seemingly “bonding” as the messaging can get, you don’t know that person and us humans tend to create an imaginary version of that person, filling in any unknown information about them with our own ideals. Trust me, it’s never accurate. And when you’ve had all that time to create this idealistic person in your head, there is no way the real person can compete. It can be something as simple as you imagining that she has a sultry voice and then when you meet her in person, she’s got a high-pitched tone that annoys you. Or she reminds you of an ex that you really don’t like anymore. At the same time, the real you might be a disappointment in comparison to the “you” that she had made up in her own mind. It’s just best to prevent that from happening and meet up before those idealistic versions have had a chance to form in your minds.

One other important thing… I mean it guys, this can make or break your chances with a woman. When you make a date with a woman and she gives you her number, always confirm via a phone call or text. Do this by the night before at the latest. Especially when it comes to online dating, which is a place where a lot of disposable interactions occur. If you ask a woman out on a Monday night for a date that Saturday, and she gives you her phone number, confirm with her during the middle of the week. It’s super important to show that you are making that time commitment for that first meeting. Before you actually meet, she has no idea if you are a flake or are using her as a last minute date unless someone cuter comes along during the week. Same goes for her, many guys could be chatting her up and if you haven’t confirmed the date she’s not going to want to turn down Saturday invitations based on a loose plan that you gave her. It’s a mutual respect of both your time and hers if you get the plans confirmed. Remember, you only get one chance to make a first impression. When a person confirms plans, it shows them as someone who not only respects your schedule but their own, as well.

Bonus Points

So we all know that it’s part of great dating etiquette to text to confirm a date, but you are going to stand out if you take that bigger leap and make a phone call. In this day and age where so many people are afraid to communicate without the use of a keyboard, you will stand out as a man amongst boys if you call. To make my point, I’ll describe two times I knew that I was dealing with considerate and confident men before even meeting them in person. One of my dates not only impressed me that he didn’t take the easy road and text, but when he called, he was down-to-earth and made a few jokes that got some laughs out of me. This was great because it definitely got me to look forward to the date and meeting this new person. The fact that this man made the call showed me that he had confidence and knew what he was doing. The great thing about this technique is, not very many men call so if you do call, you’ve definitely placed yourself head and shoulders above the rest.

The other time I was impressed by a date was when he called me a few days ahead to set up the date. He provided a list of really nice restaurants to choose from and I have to admit, the fact that he was putting so much effort into the planning, really impressed me. It made me look forward to a real “adult” date. He made reservations, we both dressed up, he picked me up, the restaurant was lovely, he was good company… and that date is amongst my top first dates.

It was a refreshing change from the standard coffee shop dates that are commonplace in the modern dating scene. It’s just hard to get excited or invested when it’s just a quick coffee date. I know that there is so much advice about keeping your first date short in case the date turns out to be a dud. But what is that really saying? It’s prepping you for a dud date. You are not leading with the self-talk that it will be fun to meet this person. You are basically showing up to the date with that one hand ready to open that parachute and make that escape. I’m not saying that having a positive mindset will repel any dud dates, I’m just saying go in with a positive attitude and wait till the red flags are visible before you politely end the date. Then go home and enjoy some time catching up on your own interests, hang out with friends or keep looking.

The most important thing I’m trying to get across is to relax when it comes to dating. Make effective decisions and have fun. In the meantime, you are honing those dating skills so that when you do meet that special woman, you’ll be bringing the best version of yourself to the table. Remember, the dating world is a mix of painful lessons and even more pleasant surprises. Good luck out there!

unnamedConnect with Adriana Green at AdrianaGreen.comTrig & Polished, Instagram, and Twitter.




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About Adriana Green

Adriana Green always roots for the good guys. She also enjoys making good people look great. She runs a mens street style site called Trig & Polished (, in which she scours the streets for stylish men with the mission of promoting good men's style. She appreciates more than just well-dressed men; see what else by checking out her photography at Connect with her on Instagram @adrianagreenphotography & @trigandpolished

About Adriana Green

Adriana Green always roots for the good guys. She also enjoys making good people look great. She runs a mens street style site called Trig & Polished (, in which she scours the streets for stylish men with the mission of promoting good men's style. She appreciates more than just well-dressed men; see what else by checking out her photography at Connect with her on Instagram @adrianagreenphotography & @trigandpolished