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

Step 1: The Opening Message

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

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.

  • 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.
  • 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.

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.


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.



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