Wondering how to start a conversation with a woman on a dating app? You’re not alone, I was too. 

I’m average looking and don’t have exotic travel pictures. So when I matched with a woman on a dating app it was up to me to make the first move. This is a critical point in the dating cycle because it’s how you set the tone and is the first impression of your personality.

You can’t just say, “Hey what’s up” or the American Pie classic, “Blow me beautiful”. The former is too boring and the latter may be too aggressive. Woman even say in their profiles to not just say hi to them (even though they do it too). You think F@$# her for saying that because you can say what you want, but she is right. You have to come with some sizzle to spark some excitement in her.

For every one woman you match with she probably matches with five or more men so you need to say something to differentiate yourself from the pack. With that said, here are a few tips to help you start a conversation with a woman on a dating app, make a great first impression, and most importantly – really get noticed. 

Actually Read Her Profile

You should be doing this already because this is free ammunition for your ice breaking gun. What school did she go to, maybe your alma maters are rivals or maybe they have a big game coming up and you can comment on that.

Look at her pictures, maybe she has a picture of a beach in Thailand. If you’ve been to Thailand you can connect over your travels. If you haven’t traveled to Thailand, you can ask where the picture was taken because you want to plan a trip to Thailand in the future, even if you’re not.

Check out her hobbies. I once matched with a girl who liked to rock climb, so I innocently wanted to ask her where she liked to climb. But the auto-correct on my phone changed rock to rick. I noticed this but after thinking about it I went with rick climb anyway because I thought it was funny. She thought it was funny as well and we had an immediate connection and a mutual inside joke about rick climbing.

Where is she from? Are you familiar with the area and can bond over a local bar or hamburger-shack that only the locals frequent. I once matched with a girl from a small Texas town and with a little google map research I was able to strike up a conversation and make her laugh by asking which was her favorite stop light in town, because there were only two. If she doesn’t give you much to work with in her profile then why are you interested in her?

Take Time and Think of What to Say

This is going to be the first contact, so make sure you are happy with your “first message” before pressing send. There is no rush, no timer ticking down that requires you to say something now or forever hold your piece. Think about what to say that will peak her interest. Maybe come up with a few options and run them by a friend. This may not be efficient because I’m sure you match with a glut of women, but maybe for a few you really fancy.

Be Unique and Creative

You can bet that she receives four or five times as many messages as you do, so you need to say something that stands out. If she’s got five messages in her inbox you want yours to be the one that she has to pause and think about. This is an opportunity to demonstrate your personality and plant a seed in her imagination.

You want to be unique but also succinct. It may be counterintuitive but you don’t want to bombard a woman with an essay on a first message. Don’t send anything over two sentences otherwise she may not read it all. Give her a taste and let it spark her interest, and if she likes it you can elaborate later.

This is will be harder than it sounds because you need to make sure your message is clear and she can understand without being too wordy. The challenge is the balance between the two.

If you’re struggling with creating short first messages, Emyli wrote a great article on the Best Tinder Opening Lines for Guys that will guide you in the right direction. 

More on Conversation Starters

Your first comment shouldn’t just be to introduce yourself or demonstrate your personality but should also be a question to start a conversation. You’re reaching out to her because you want to get to know her better so beyond saying something unique and humorous you need to spark a conversation.

Also never let the conversation drop, keep asking questions. When this gets tiring or you think you are boring her then bookmark the conversation and give it an open ending to continue later. You can say, “It was fun talking tonight but I have to get up early tomorrow” or “I’m meeting friends for dinner, I’ll hit you up later.” Woman like it when they know they will hear from you again and it’s a subtle way of showing that you are interested in her and want to continue getting to know her.

Read your Audience 

Funny and clever are good ways to get her attention but try to gauge her personality from her pictures and what she’s written in her profile. If she has pictures with her boobs hanging out or talking about no strings attached then maybe go the more aggressive, risqué route. If she has a picture with grandma and talks about teaching Sunday school then maybe make it G-rated.

Timing

Just like the stock market or buying a home, timing is everything in dating. If you don’t think you can be unique then maybe time your message for when you think there will be less competition for her attention.

I found women to be most responsive to opening messages on weekend mornings. They are likely to be less busy compared to during the week and maybe they hung out with friends the night before and are feeling a little lonely or vulnerable. They are looking for a relationship but woke up alone in their bed again and boom here comes a funny message from the guy she matched with a few days ago.

Ok, So When Should I Message Her?

If you match on Monday I wouldn’t wait until the next Saturday – but if it’s Thursday or Friday maybe save that message until Saturday. Or if you want to plan ahead don’t look at your apps in the beginning of the week but start getting some connections in the pipeline on Wednesday or Thursday so you can match and strike by Saturday.

Examples of How to Start a Conversation With a Woman on a Dating App

How to Start a Conversation with a Woman on a Dating App if She’s a Kindergarten Teacher

Example 1: How do you like your little monsters? – That’s good, funny gives her something to work with and respond to.

Example 2: How do you like your little monsters? When I was that age I couldn’t figure out which shoe fit on which foot. – Good as well, cute, clever and a little self-deprecating.

Example 3: How do you like being a kindergarten teacher, I have niece in kindergarten and she is so cute? – Good and it gives you something relatable to discuss.

How to Start a Conversation with a Woman on a Dating App if She Just Traveled to Belize

Example 1: I love your pictures where was that, it reminds me of the ruins from Indiana Jones (Tomb Raider for those of you under 30)? – Funny, creative and again gives her something to work with.

Example 2: The parole board took away my passport but I have always wanted to travel someplace exotic; do you have any suggestions? – Funny and gives her something to think about. You would have to gauge her sense of humor for something like this.

Example 3: Look at you Dora the Explorer, did you find any lost civilizations on your expedition? – Clever, G-rated comment.

How to Start a Conversation with a Woman on a Dating App if She Moved Here From London

Example 1: Is there a translator between proper English and what you speak? – Clever and kind of a smart-ass remark, so you would want to gauge her sense of humor beforehand.

Example 2: What do you miss most about London, the rainy weather, warm beer, or bad food? – Again, another smart-ass remark so gauge your audience.

Example 3: I’ve always wanted to go to London. I recently got into the Premier League and love Crystal Palace. – Unique as most Americans would have no idea who Crystal Palace is, but make sure she is a sports fan.

Don’t Over Message

My last recommendation is about being over reliant on messaging. If you create a good rapport, then get her number and don’t be afraid to call her. You will definitely stand out if you do so because men don’t call women anymore. After I matched with a woman and we hit it off, I always gave them a call before the first date. They were surprised but they appreciated the old-fashioned gesture and respected my confidence and courage.

Woman like confidence and going out on that limb to call her is a good demonstration. I also used it as a kind of screening process. In my mind if you can’t have a conversation for 10 minutes then maybe you shouldn’t waste your time with a date.

In Conclusion

It’s tough out there and there isn’t a magic recipe or secret formula that works on every woman. Steph Curry didn’t immediately start draining three pointers when he first picked up a basketball, and dating is a skill like everything else. It may come easier for some but for the majority it will take a lot of trial and error and tweaking of your approach to refine your message, image, and vibe you want to exude. If you take the extra effort and assimilate some of these tips with your own gut instincts you will give yourself a better chance of catching her eye.