How to ask woman on a date

Since being a teenager I always remembered having high libido.All I could think of was the girls in my school. Unfortunately, I was one of the least popular boys so any kind of dating was out of the question.

I was too shy and awkward to ask anybody out anyway.

When I was 19-years old I remember my first time asking a girls phone number. She smiled at me and said no…

Beautiful woman sitting

My biggest progress was when I actually got a girls number but later fucked it up by being too needy in my text messages which turned girl off.

I was a 19-year old virgin. How am I supposed to lose my virginity if I can’t even get a girl a date with me? What am I doing wrong?

I was crushed, I felt like a total loser and outcast. But I didn’t give up, thanks to my high sex drive I was willing to get rejected  time after time. My attitude reminded Jeff Allen´s journey in his diary “Get laid or die trying”

At age of 21, I finally got a girl agree to go on a “date” with me, yippee. She was a cashier girl 2 years older than me working at the supermarket where I worked as a security guard. We clicked so I stalked her on Facebook like a creep. She approved my friend request which was a step forward.

I made up a story how I got these tickets from work to aquarium zoo. I bought them myself 😉 Pretty sad I know.

This time, I wasn’t acting needy which was good,I only became needy after the date which once again killed my chances with the girl.

Holding a flower

Anyway, it took years for a social retard like me to learn whole dating thing and asking girls out. It was really hard for me. It was quite awkward.

I used online sites likes OKCupid a lot. I spent a lot of time on online dating, it was like an obsession at one point.

These days asking a woman out is not a problem,it has become automatic. If I m interested in somebody I will ask them out.

Asking a woman out shouldn’t be a big deal to you. Even if it is, don’t show it. Play it cool. You are interested in somebody and somebody might be interested in you, it’s natural. There is nothing to ashamed for. We are wired for this.

The most important thing I learned over these years is to keep things as simple as possible. The girl either is interested in going out with you or she isn’t. If she isn’t interested why waste time on changing somebody’s mind? Just move on and find a woman that is interested.

Woman in red dress sitting on the couch

I did this mistake many times in my younger days where I tried to get the girl to go out with me, it never turned out good for me.

So how to ask a woman out?

After interaction on the phone (I interact only on WhatsApp)

Say “You are kinda a cool. We should go on a glass of wine together”.

“You are kinda cool I want to take you for a glass of wine”.

“Lets go for a glass of wine

Recently I say “we should go for tea/glass of wine sometime”

Tinder conversation

Tinder conversation

Tinder conversation

Tinder conversation

Saying it like this is affirmative and conveys value. You are interested in her and you want to have a drink with her. You are already assuming that she will go out with you instead of asking. This shows confidence in yourself and we all know that women love confidence.

Do not use these:
“Would you like to go with me…..”
“Can you go with me”
“Do you want to go with me”
“Can I see you”

They sound low value and needy. It’s asking permission and it´s putting the girl on a pedestal. Women don’t like that kind of a behaviour. Using lines like that make you look like a guy who doesn’t date much.

Wonderwoman & Superman

Even if you don’t, don’t make it obvious, fake it till you make it.

At times I was nervous as fuck when asking a girl out but I tried to play it cool as best as I could.

Avoid also using word “date”, it makes things too formal and sets a too serious tone. The girl might get anxious going on the date. You are just going for a glass of wine to see if you have any chemistry together.No big deal.

Pretend that she is some cool guy who you wanna have a drink with me. You don’t ask a guy “Hey dude would you like to have a drink together “.

You say “Hey dude lets get a drink together”

You assume that another person is already interested in hanging out with you. These days I interact with women like I would with my buddy, laidback and relaxed.

You see how much little small things matter.

Now back to the wine.

I like to drink (in moderation) in a good company. When you drink things get to be more interesting at least in my case. It loosens and relaxes us. But don’t get too drunk…

Women love wine.It’s romantic and socially acceptable drink. What girl can decline a glass of wine? When I picture wine I always get a picture of candles, romance, flirtation, french kisses but then again I have a very good imagination. 😉

A glass of wine is a low investment for a girl, it’s only one drink. You are not asking much. There is no pressure of any kind. Even if you don’t have chemistry on a date its okay you drank some wine, time was not wasted ;).

Girl drinking wine

I want to make the girl as comfortable as possible, she can just sit and sip a wine with me.
I expect nothing, it’s like chatting with an old friend.

Of course, if you can’t drink then its ok to drink tea or juice on a date. I just like wine more. I recently use Tea/wine option with a girl in case she doesn’t drink at all.

Tinder conversation

I m also lazy in this kind of things so to me going for a drink is much easier than going to a restaurant to eat or taking a girl to zoo hang out.I know people who take girls to play mini golf or pool but I don’t do it. I suck at both by the way so I would just embarrass myself.

Asking a girl to play mini golf or to do some form activity may trigger her insecurity, playing mini golf with a total stranger is not very pleasant experience. If a totally random girl asked me to go play golf with her I would say fuck no. That’s too big investment and is not casual.

Woman drinking at the bar

Drinks are my favorite thing. Easy and simple.

When asking a woman a date make sure to make the date as soon as possible. My period is 3-9 days. People have short memories and can lose interest quickly. 2 weeks ago she was interested now she doesn’t remember you. The vibe on the phone can die quickly, so it’s important to go on a date as fast as possible.

If you have lots of time before date make sure to be on her radar. Send a funny text or a picture 2-3 days before the date. This will keep warmth in interaction.

I myself love posting cute stuff like my friend’s dog or some funny meme. This keeps easiness and comfort between you two.

Cute chihuaha on the bed

I did a lot of mistakes when going cold on a girl, then before the date, she would cancel.Then I would try to slit my wrists in my bathroom crying….Just kidding.

Where to set the date?

I love lounges and bars that don’t have a lot of people. Too many people irritate me and it’s not as intimate. I have my own places that where I feel like I m home. That’s a good thing when you feel comfortable in a dating environment. If its summer you could always go to a park and drink wine there.


Asking girls out should be easy and natural. But for guys like me it took years to learn the art of dating. Some of us aren’t comfortable with dating. But the good news is that with a little bit of effort we can learn new things.

You don’t lose anything asking a girl on a date.Except maybe your ego will get hurt and your self-image gets a hit. It’s not life threatening unless if she is a girlfriend of mob guy 😉

If you are interested in some girl, go ahead ask her out on a glass of wine. How could she refuse? Just go for it, tiger.


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