Get More Dates With
Captivating First Messages

Online dating sucks for most guys. They send first messages endlessly with no results and constantly tell me how useless it is.

Therefore, I have made it my mission over the years to really decipher the online dating code.

Why do some guys have success where others fail? What kind of messages get responded to? What gets ignored? And are there any consistent patterns?

In my research, I’ve found that a woman’s #1 fear online is that a guy will be awkward, creepy, or intense in-person.

They don’t know you, they haven’t met you face-to-face, and they don’t want to get stuck on a bad date. I’ve heard countless horror stories and can’t blame women for being cautious.

Your only goal in the first message is to assure her that you’re a normal guy. You accomplish this by creating a fun, enjoyable atmosphere that gets her excited to reply.

Your Photos Dictate Her Responses

To start, there’s one thing you should know that will greatly affect how women reply to you…

Fix your damn pictures!

I did a huge post about it and nearly all of the profiles I critique suffer from crappy photos.

Their pictures are unflattering and blurry. The guys don’t smile. They are unkempt and wearing baggy, ill-fitting clothes. And all their photos are sitting around doing much of nothing.

Seriously, your pictures are all a girl has to go on to determine whether or not you are an axe murderer/pedophile/stalker.

Care about taking high quality shots and coming off as a guy who has an interesting lifestyle.

11 Rules For A Successful First Message

1. Use proper spelling and grammar.

Spell check and re-read your sentences before you send them. Make sure you have all punctuation necessary. This seems obvious but I always read messages that aren’t tidy.

2. Emojis are your friend.

You don’t have to use them every time, but they can definitely help. I’ve tested this and often the responses I get are to my messages that include them. It can soften a message and convey a cheeky or flirtatious tone.

3. Don’t limit your message to info at the top of her profile.

Unless something really stands out, find something a little further in to talk about. It shows you went through and actually read her profile.

4. Keep it short and pithy.

1-4 sentences at most. Trim ruthlessly and cut out any excessive words or unimportant details.

Think in emotions, not facts. All you’re showing her is that you can be fun, easy going, and can make her laugh.

You might think that writing a thorough message would be more effective — it’s not.

5. Find something that genuinely intrigues you about her.

If there’s something you both have in common (kayaking, being a burger snob, photography), that’s always a plus. This is always a better idea than bullshitting because if you do get her on a date, it’ll be obvious that you were dishonest.

6. Stay positive and playful.

There should be no negativity in your message and don’t get into anything serious. She should always open her inbox and smile; lightheartedness is key.

7. Avoid being mundane or generic.

No asking her how her day is or saying “I thought your profile was cool, we should talk.” Stuff like only saying, “Hey” and “What’s up?” is out, too. You have to be a bit creative and put some thought into it. (Examples below)

8. Limit yourself to one compliment maximum.

Many times, you don’t need to compliment in your first message. But, the occasional genuine and well-placed one is great.

I’ve seen guys overdo it with, “You like Thai Food? That’s awesome! You have really cool taste in music. I like your pictures, they’re cute.”

She’s going to question why you’re sucking up to her so much when you don’t even know her and she hasn’t earned it. This is a big turn-off

9. Don’t be Mr. Agreeable.

Just as with compliments, a guy who tries to seem like he’s perfect for her looks desperate. You don’t need to convince her how similar you are.

One commonality is enough but avoid messages like this at all costs: “Oh my god, Community is my favorite show, too. That’s great that you are into hiking, I go all the time. And I’m a huge fan of Mexican food as well!”

10. Avoid being overtly sexual.

I always advocate being forward early on, but in online dating it sets girl’s alarm off.

Remember, she’s worried that a guy will be creepy and without seeing you, being sexual off the bat is not your strongest lead-in. It’s also unnecessary to get her out, save it for the date.

11. It’s okay to be a little challenging or flirtatious!

Let her know a quality or quirk that won you over. Ask her a thought-provoking question. Gently tease or bust on her for something she said. Even make a statement of interest about something you liked (dimples example below).

Good First Message Examples

Here are some examples and explanations of how to implement the above guidelines:

Example #1

What I’m doing with my life

“…I just like to rock out with my figurative cock out.”

The first things people usually notice about me

“are usually off the mark. But mostly it’s that I am pretty unfiltered.”

My message:

“Not sure how I feel about your figurative cock haha.

You say people misjudge you at first, how so? Tell me something interesting I wouldn’t guess about you :)”


So this girl is more rowdy and colorful with her words. This means I can be a little ballsy in my approach.

I’m teasing her about “rocking out”, showing I read her profile, and that I want her to share something personal. This demonstrates I also have standards and I’m not desperate.

Example #2

The first things people usually notice about me

I’m pretty freakin’ sassy

My message:

“How sassy are we talking? A cute, snappy comeback or a full-on “Oh no you diiin’t” with some finger waving action?

P.S. Your dimples are adorable.”


She says she has an attitude so I’m challenging her on that and poking fun. I’m exaggerating the stereotype of someone with a ton of sass in a humorous light.

I noticed how pronounced her dimples were and I genuinely thought they were adorable, so I told her. This combination of being carefree yet direct lets her know I’m attracted to her without being creepy.

Example #3

I’m really good at

“…doing accents…”

Favorite books, movies, shows, music, and food

“I love most foods, except for olives and button mushrooms.”

My message:

“Your similar distrust for olives and mushrooms caught my eye 😛

I’m intrigued, what’s your signature accent? I can do a spot-on Kermit the Frog when necessary.”


I hate olives with a passion and so does she, so why not joke about it?

I also found the fact that she likes doing accents hilarious. Asking her about it is non-threatening and a unique way to start a dialogue between you two. She’ll likely smile while thinking of funny memories and be inspired to respond.

Example #4

The most private thing I’m willing to admit

“i hated losing teeth as a kid! it was sort of traumatic, actually.

my favorite games to play are apples to apples, uno, and bananagrams.”

My message:

“Your profile made me Google “bananagrams”. Thanks, like I need something else to be addicted to ;p

Have you ever had the “teeth falling out” nightmare? It’s quite terrifying.”


I’m into board games like apples to apples so I really googled bananagrams.

I’m opening up to her, admitting I like something nerdy, and teasing her about it as well. It’s cute and again would get most girls laughing.

I follow it up by sharing a nightmare that I’ve had which relates to one of her private fears. That creates an instant personal connection and provides incentive for her to message back.

Do Your Best and Accept You Can’t Always Win

When in doubt, these two elements are always a winning combination: a tease / playful flirtation / funny joke AND an open-ended emotional question.

Unfortunately, there is no magic formula that will get women responding 100% of the time.

Some girls just won’t reply, it’s inevitable and part of the process. Accept it, don’t take it personally, and keep pressing on.

Use the guidelines to improve your chances for next time.

Always have fun with your messages and stay genuine. Girls can sense you being fake and even if they don’t at first, they will when you meet.