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The Dating Guy

How to Ask a Man for a Date

Updated: Oct 19, 2023

Pre-Date


Well well well, look at you, I’m surprised you got this far. I joke I joke, I’m proud of you. You finally approached a man and successfully got his number. Now what? That’s it. Your life is complete, retire and live. SNAP THE FUCK OUT OF IT. You literally just climbed the first step of the staircase. Be better.


In this section, I’ll guide you on how to ask a man for a date, what/how to text him or say to him in order to get/confirm a date. If you didn’t ask for his number with a statement such as ‘let’s have dinner/lunch/drinks some time’, then you still need to GET a date. When I say confirm, this means you did ask him for dinner/lunch/drinks as you asked for his number but now you need to CONFIRM when and where you’re going, what cuisine you’re going to eat if you’re getting food amongst a few other things. So, I’ll split this section into two parts – Getting a date and Confirming a date. ARE YOU READY?


But first, I’m going to give you some advice on texting. Since this is the first time you guys will be texting, its best to keep the small talk limited. Now ladies, since you were so charming and funny when you approached him, he’s gonna want to text you, so be ready! What I would recommend is to keep is as limited as possible. Don’t ask too many questions about him because you don’t want to ask him everything now and then on the date you just sit there awkwardly sipping on your drink and twiddling your thumbs – do people even twiddle thumbs anymore? - because you have nothing to say. DON’T BE AN IDIOT.

A picture of a man proposing to a women in front of a sunset.

You want to know a secret POWER MOVE that will literally make him want to propose?? Well not literally and it might not even work but it’s a great way to build confidence and just try something that might be a home run! You ready?!!! CALL HIM TO ASK FOR THE DATE. You might even get him to want to meet your parents with this move. I’m kidding, don’t be that girl that’s already planning the wedding.


The reason why I call this a POWER MOVE is because WHO DOES THAT THESE DAYS. You’d be surprised at how refreshing it can be to see someone do something so uncommon. Let’s be honest here, YOU’RE NOT SPECIAL. You’re probably not the only girl who’s asking him on a date. Shit, if you found him attractive, I’m sure atleast a few others did too.


But you can be the ONLY GIRL who actually called him and that would definitely differentiate you from the other girls. Now, what do you do when you call him? Easy. You breathe loud on the phone for a bit, say nothing and then hang up the phone. IM KIDDING, PLEASE DON’T DO THAT. Keep reading.


Calling him to ask for the date


Keep it quick. Keep it simple. Keep it to the point. Pick a date that’s close to the day you guys met, no longer than 5 days and better to do Friday or Saturday as that’s when people are usually free. So as long as you met him before Friday or Saturday, even it’s a day before, you can ask him for the Friday/Saturday. Remind him who you are by saying your NAME and if you want, you can make it funny.


Another piece of gold here, MAKING FUN OF YOURSELF in moderation can be very attractive. It means you have the confidence to acknowledge your flaws and laugh at them.


So, for example, you could say something like, ‘hey it’s the girl who awkwardly complimented you – insert what you complimented him on – today, how’s it going?’. Then, whatever he replies, which will likely be, ‘oh hey HAHAHA how’s it going?’, you GET TO THE POINT. You can maybe be like, ‘yup I called you, cut me a break, I’m trying to be confident here haha’.


Wait for a reply. Then say something like ‘Figured I’d just call you and see if you were free Friday at 730pm for dinner’, he may say yes and he may say no. If he says he’s busy, RESPECT THAT. ALWAYS HAVE A SECOND DAY READY. Offer him that day as well.


Now, if he says YES, end it with something like, ‘Great, I’ll see you then’ or something funny, like, ‘get your stomach ready for tacos’ if you’re going to get tacos. Whatever it is you have planned to eat, MAKE SURE HE LIKES IT. ‘But How do I make sure he likes it??”. GOD do I have to tell you everything??!! Alright, you ready for this? ASK HIM.


After you say 730pm, ask something like, ‘by the way, do you like tacos?’ and LISTEN TO HIM REPLY. If he says yes, then great, if not, then say, ‘Alright, well, be ready for 730 anyway, ill text you some options.’ This shows that you’re committed to the date while also showing him that you CARE ABOUT HIS PREFERENCES.

A picture of two cartoon tacos in love.

Now, I’m telling you this because I’m a funny guy, as you clearly can tell. So, if I were a woman, normally I would say something like this if he said YES to tacos, ‘Okay great! Because if you said no to tacos, I was about to hang up and delete your number HAHAHA’ and if he said NO, then, just run. IM JOKING, NOT EVERYBODY LIKES TACOS.


You can say something like, ‘YOU DON’T LIKE TACOS?!!! This isn’t going to work out, bye’ Then tell him YOU’RE JUST KIDDING hahahaha. You might even be able to gauge here whether he enjoys your humor or not, because that way you can adjust your jokes accordingly or if you don’t like that about him then maybe he isn’t for you and that’s okay.


NOW WHAT IF HE SAYS NO TO GOING ON A DATE WITH YOU whether it’s right away or even after you’ve asked him multiple times. Then it’s simple. Don’t ask him why not. Don’t ask him why he gave you his number. Don’t question it. Just say, ‘Oh, that’s alright, I respect that, it was nice talking to you, hope you have a great day’. That’s it and you’re done. MOVE ON. Buy some ice cream, put on a romantic movie and just cry. OR JUST DON’T GIVE A FUCK.


Texting to ask for the date


Keep it quick. Keep it simple. Keep it to the point. Honestly you can say exactly what I’ve told you in the calling section above. Then after you’ve received an answer, DON’T TEXT HIM TILL A DAY BEFORE THE DATE.


If he texts you, that’s great because then you know he’s not busy but even then, don’t overdo the conversation. Ladies, men enjoy when you take the initiative to flirt a little so if you want, you can do some light flirting or a fun conversation but DON’T OVERDO IT.


Leave some mystery/curiosity to it, give him vague answers because it’s better to save it for an actual face to face conversation. Otherwise, it’s alright to assume he’s busy.


Plus, you want to wait till the date to showcase your humor and GET TO KNOW HIM. A day before the date, send him a SIMPLE MESSAGE. ‘Hey, just wanted to know if we’re still good for tomorrow?’ That’s it. He says yes, then you just say ‘Great, see you then!’. If he says he can’t then DON’T ASK WHY, just respect it and offer him another day. That’s it. If he still says no, then ASK HIM WHAT DAY HE’S FREE. Guys, this is easy conversation. Just keep it casual.


WHAT IF HE KEEPS PUSHING THE DATE OR CANCELING? Well, what I advise is this, if he cancels or reschedules more than twice, then RESPECTFULLY tell him to schedule it. Tell him something like, ‘Hey, it seems that the days I’m picking aren’t working for you, I’d be open to you scheduling a day that works best for you, let me know’. THAT’S IT.


A picture of footprints in the sand with a quote saying, move on.

Don’t keep waiting for him reply. Don’t keep asking him what day. NOTHING. JUST KEEP ON LIVING YOUR LIFE AS IF YOU NEVER MET HIM. You don’t want to seem as desperate as we all know you are. IM KIDDING.


The art of NOT GIVING A FUCK. Remember that. If he replies, that’s great, if not, it’s because you smell. IM JOKING. Maybe he’s not interested but he didn’t know how to tell you. It’s alright. You JUST MET HIM. MOVE ON.



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