How to Ask a Man on a Date - Cool Dating Advice

How to Ask a Man on a Date

You really like a certain man but he has not asked you out but he has shown interest. What do you do just go through life not taking any chances? Should you ask him out and how do you ask a man out? This is really a straightforward answer you just go up to him and ask him if he would like to do coffee or lunch one day next week.

I know that sounds hard to do plus you are scared of rejection. The worst thing he says is no but the best thing is he could say yes. We need to look at some strategies for a woman asking a man out in today’s world.

You need to ask him out at the right time and place

You want to ask a guy out when there is not a lot going on and it is casual. Pick a time and place where you can get him alone with nothing pressing going on. You could maybe ask in a hallway at work when you see him or maybe if you know him from the gym ask him after he has worked out.

The keys:

  • You could walk over and say, “Hey can I talk with you a second?” Then pull him to a private area to ask the question about meeting out some time for coffee
  • You need to make sure you have privacy. You do not want to do this in front of a crowd
  • Do not text asking to go out or call over and over only to hang up when he answers. This is creepy and you would seem more like a stalker than someone that wants a date
  • Play it smart making sure what you do is casual and no big deal

Have what you want to do with him in mind

  • It is better if you are decisive instead of vague. When you ask him out say,” Hey did you want to meet at 8 AM tomorrow morning for coffee at Starbucks?” If he cannot make that date he will tell you, then hopefully he gives you an alternate day and time.
  • If you know something he likes to do such as go to a football game. You could say,” Hi Jim I have an extra ticket to the Chicago Bears game did you want to go with me?” Make sure he is a fan of the team you want to take him to see.

Can you have an exit strategy if he says no


You never know what is going on in their mind when you approach him to see about meeting out. If you come up to him and you are not feeling good vibes then maybe hold off.

  • You get the sense he is not in the mood or the timing is bad for you to ask him out. Just switch to an alternate question to get out of there. You can always ask at a time that may seem better, where he is maybe in a more jovial mood
  • Make sure you have an alternate question before approaching him

The extra ticket ask out

We mentioned this earlier but lets elaborate.

  • You can walk up and start a conversation with the guy you like. While talking casually mention the event you have tickets saying your friend bailed and you are stuck with an extra ticket. You can even say,” Hey don’t you like the Cubs did you want to use the extra ticket and go with me?”
  • Make this a casual ask but do show interest in him. You don’t want him thinking its just a friend thing because your other friend bailed. You want to give him some hints you are interested

The only big issue is the guy could go just to see the game and not really be interested in you. I would at least have a small idea that he has an interest in you before trying this technique.

Group date

You can use the group date approach if you think it will work with the guy. Call or text to say you and some friends are going bowling did he want to join.

  • You can do this with bowling
  • Group dinner
  • Group movie
  • Everyone going to a popular club
  • Dancing

The things you can do as a group date are endless. A group date takes the pressure off you both. You can now both interact to see if there are any sparks or if there is any chemistry. If there is some chemistry maybe he will ask you out for a second get together.

Movie or concert strategy

You like someone and you are talking about general subject matters. You want to ask him out to do something so how do you go about doing it?

You need to mention a movie that is popular with both men and women. If he says I really want to see that movie or a concert you mentioned then you say,” Great did you want to see it this weekend with me?”

You can go on to say,” Many of my friends do not like that band so that is great that you like them like I do.”

The old note-passing technique

We did the passing notes in school, where the note said do you like me with two boxes one saying no and the other saying yes. You would check the box and pass the note back. Here you can leave a guy your number on a card or napkin.

The note can be real casual like,” I talked with you tonight and had a good conversation, did you want to grab a coffee next week? Call me at phone number” This way if you do not get a call you know he was not interested but it was not an in your face rejection.


You can also use the phone to ask someone out if you know them a little bit. Just give a call and talk with them for a little bit to see how they are reacting. Once you have a good vibe then see if he wants to do something next week.


You can also do this with texting but like we said earlier make sure he knows who you are before texting him to go out.

Face to face

You can also just do it old school. You can go right up to him at the right time and place to ask him to go out. This takes more guts but you have nothing to lose. The only thing he can say is no but if you never ask then he will also never say yes.

Times have changed in today’s dating world. Women can now easily ask a man out if she is interested in him.

Use some of the techniques we have listed above to help you land the guy of your dreams or at least land the guy you like now. Remember if you do nothing you get nothing so get off your couch and go meet some men.

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