How To Ask A Woman Out On A Dating App: A Guide For Men

10 min readJun 30, 2017


Hello and congratulations! I hear you have come across a dating profile that you enjoy. This is, of course, the first step to any online dating interaction. Maybe you like her photos, maybe she said something that made you laugh in her bio, maybe you were lucky enough to find a combination of the two! Either way, you are probably wondering, “What do I do next? These women, these mythical creatures, they are just so complicated! How ever will I move forward?”

Now while you could easily have already done such things as “Listen to your female friends” or “Observe women on Twitter talk about dating and be thankful for the free and plentiful advice,” we won’t dwell on the past, dear reader. We will pretend you haven’t chosen to willfully ignore all information that has been presented to you in the past, and we will instead look to the future…a future that hopefully ends with you and this wonderful profile you see before you, deep in love.

Step 1: The Opening Message

Now, how you begin a conversation will depend on what app or site you are using.

If you are on a non-matching site like OKCupid or PlentyOfFish, you have more of a profile to work with and make conversation from, but you also run more of a risk that she will not respond as she has not already signified interest via swiping. Please don’t take this personally; however, please don’t see this as a reason to make no effort either.

If you are on Bumble, you unfortunately have to wait for her to message you first. When she does, you might want to try this crazy idea called “responding.” It’s really that simple. Respond. See what happens.

If you are on Tinder, you are free to make the first move if you want. Now here is where things start to get tricky…I’m going to need you to resist all urges to just say “hey” or “how are you.” I know that every fiber of your being is willing you to write the most generic and boring message possibly known to man, but reader, please resist! Your brain might be telling you, “She will be unable to resist the charms of this ‘hey,’ this is surely the move,” but allow me to act as your heart and your conscious and tell you this is an awful idea. You can say almost anything else. Ask a question about one of her photos, make a witty comment about something in her bio, please just do SOMETHING to stand out from the crowd.

Step 2: Don’t Suck At Conversation

Reader, do you enjoy job interviews? Do you enjoy being peppered with boring questions that you feel you have answered a million times before? I am assuming the answer is most likely no. So, I implore you, please do not inflict this pain on women.

There are any number of ways to make good conversation, and I can’t possibly list them all as they are so situational. But here are some good starting points:

  • Ask about where one of her photos was taken if she is clearly traveling and when she responds, follow it up with a story about your own travels
  • Ask about something in her profile, and when she responds, follow it up with a story about you or someone you know that relates to what she is saying
  • Ask about her job, but more than just what she does, ask why she does it, how she got into it, what she likes and dislikes about it and if she doesn’t ask you some of these questions in return, she probably isn’t all that interested
  • When something she says reminds you of a television show or movie, ask her if she has seen it. If she says yes, discuss. If she says no, describe the show and why you like it and recommend it.
  • Ask about any pets in her photo but only if you have something interesting to follow that up with such as “I volunteer with an animal shelter in my free time.” If all you have is, “Cool, I love dogs” then just skip this line of questioning.

Are you sensing a pattern, reader? A conversation should flow. It should be two people sharing information and asking each other questions. If you are asking a million questions and not sharing anything about yourself, you are boring her. If she isn’t asking you any questions or is responding with very short answers, she probably isn’t interested…that may be because she is just not interested, but it may be because you aren’t doing a good job at making conversation. Try a new technique, but if she continues to not give much, then just move on.

Here are some things you should not say when making conversation:

  • How are you?
  • How was your day?
  • How was your week?
  • Where do you work? (you sound like a stalker)
  • What do you like to do with your free time? (there are other ways to gather this information without asking this question)
  • Have you had any success on here?
  • Have you gone on any dates from here?
  • Do you like this app?
  • Have you ever hooked up with anyone from here?
  • Why are you single?

Step 2a Through Infinity: Don’t Send a Dick Pic

Now, reader, I know that you, as a man, may not be able to understand why a woman would not want to gaze upon your penis at any possible opportunity. I know you may be enjoying a conversation with a lady and think to yourself, “I bet I know what she wants…and that is an unsolicited photo of my junk.” I understand that as she tells you some of her favorite TV shows and movies, you may interpret that to mean, “But I would rather look at a photo of your dick than the television.” I empathize with the fact that as she is telling you what she does for a living, what you might be hearing is “But what I WISH I could do for a living is look at photos of your penis all day long.” Reader, I am here to tell you, that these interpretations are not accurate. Please do not ever send a woman a dick pic.

The only instance in which you may consider sending a woman a photo of your dick is if she says the exact words, “I would like you to send me a photo of your dick.” Even then, you might want to pause and consider the context of this situation. Was there a build-up to this request? Did it come out of nowhere? Can this person be trusted or might they be doing this to post on Twitter or to laugh with their friends? I know this may be news to you, reader, but you are not legally required to send a photo of your penis, even if it is requested; that said, a request is the only acceptable circumstance to ever send one.

I know as she is sending you photos of her dog, or her breakfast, or a cute selfie she took this morning, you may feel compelled to reciprocate with a photo of YOUR favorite thing, but please, reader, try your best to refrain.

Step 2b Through Infinity: Don’t Insult Her

At some point in your conversation, this woman might go awhile without responding. Or, she might say something you don’t agree with or don’t like. Or, she might just politely tell you she is just not interested and wish you the best. I know that in these moments, your natural reaction might be, “Say something mean, that will win her over.” I understand that if you don’t hear from a woman for 24 hours on a dating app, you might think, “If I call her fat, that will get her talking to me, and then she will surely go on a date with me!” If she tells you she isn’t interested and wishes you the best, you may think the only logical step is to tell her that you were actually never interested in her and were only messaging her to be nice — the way that people in movies quit a job after they’ve already been fired. Again, reader, I am sorry, but I must tell you that your natural instincts are leading you wrong in this case.

When you find something mean about to flow through your fingers, onto your keyboard, and into the dating app abyss, I urge you, to instead just…not do that. Say nothing. Or even try saying something nice. I know that calling a woman fat or ugly or any number of other insults might seem like the most logical way to get a date, but a woman’s mind is like a labyrinth; I do not expect your simple male brain to be able to navigate the convoluted twists and turns of what makes a woman tick. That is why I am here, to help you understand that a woman is probably not going to want to date you after you call her ugly. I know it seems counterintuitive, but just trust me on this.

Step 3: It’s Time To Ask Her Out

Here we are. The crucial step. You have been talking. The conversation has been flowing and both parties have contributed to it equally. You have resisted all urges to send photos of your penis and to be mean. You are ready to ask her on a date.

Now, I will admit, every woman is different in terms of the amount of time she likes to message before going out on a date, and the type of date she likes to go on. Some woman want dinner, some just want coffee or a drink. Some woman hate going to the movies for a first date. There are no hard and fast rules when it comes to this step but there are general guidelines.

Guideline One: ASK CLEARLY

However you are going to ask, actually ask! Don’t do things you think are cute or coy such as “How would I go about asking a beautiful woman such as yourself out on a date?” I know you think that is very charming, but it’s not. Just ask.

Guideline Two: Use Previous Conversations

If she mentioned that she can’t live without coffee, ask her to coffee. If she mentions that she loves whisky, invite her to a whisky bar. If she said she likes trying new cuisines, invite her to a restaurant that serves original food. If you don’t know enough information about her to suggest a good date, your conversation thus far has probably not been that great and you should probably find out more before asking.

Guideline Three: Actually Pay Attention To Her Response

Women can respond to being asked out in a variety of ways. Some might apologize and say they are not interested. Refer to step 2b here and avoid all urge to say something rude. You might feel like you wasted your time getting to this point only to be turned down for a date, but the reality is, sometimes this is the nature of online dating. Wish her the best of luck in her search, and move forward.

Some might say they are enjoying your conversation thus far, but they need to message a little longer in order to feel comfortable meeting. Now, reader, I know that when you hear this, your first instinct may be to erupt in a fit of rage, and demand this woman tell you why she is even on a dating app if the intention isn’t to meet up. You, as the problem-solving man you are, might try to come up with some solutions to her worries such as “We can meet in a public place,” “We can FaceTime so you know I’m real.” You might want to give this woman a run-down of your resume, pointing out that men who do your specific job would never harm women. And while these may seem like excellent ideas, they are not. If you are really interested in this woman, the only logical response is to say, “Okay, I understand, I’m enjoying this conversation and would love to meet in person sometime but I don’t want to pressure you so please let me know whenever you are feeling comfortable and ready” and then continue to message her and make good conversation for awhile. No one wants to get into a cycle of endless messaging, so at some point if she never says she is okay meeting, it is okay to back off. But if you’re really interested and have been messaging consistently, my advice would be to give it at least a week or two before giving up. Every woman is different here, but the key is, respect that women have real safety concerns.

Some women might say yes, they’d love to go on a date with you. Now, I know this next part might seem like it should go without saying, but unfortunately it needs to be said — actually plan the date. People these days are very busy, it might be another week or even more before you can meet up. But actually suggest dates. If a woman says she’d like to go out with you, you might feel like the appropriate response is “Okay great!” Reader, this is not how you make plans. If she says she is interested, capitalize on said interest. Make the plans. Do the damn thing.


Congratulations, reader! You have set up a date with a woman! By following these steps of things-that-shouldn’t-have-to-even-be-said-but-apparently-do-actually-have-to-be-said, you are one step closer to finding the woman of your dreams.

On the morning of the date, text to follow up! “Just wanted to make sure we are still on for [time] at [place], looking forward to meeting you!”

Now, I will admit, a million things could still go wrong. She could ghost. The date could be boring. Making it to the date stage is just the first step, but it’s unfortunately a step that doesn’t happen often enough.

Hopefully you will enjoy the first date and she will be willing to go on a second. But regardless of whether or not this is the case, please continuously refer back to rule 2a, and do not send her a picture of your dick.




Lover of dogs, food, coffee, bourbon, and exploring new places.