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Your First Time Asking Someone Out / Picking Someone Up

User#6517

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I am very much an introvert, but I’m trying to become more social and less.. reserved. As weird as it sounds, one of my goals for this year is to take initiative and approach a man for the first time. I’ve never done it, due to fear of rejection.

It seems like most people on this board aren’t afraid to take the lead, so I am curious to know what your first-time experiences asking someone out or picking someone up were like.

How did it go? And if it was not a good experience, is there anything you wish you could’ve done/said differently?

Thank you in advance :)
 
It's like going for a swim for the first time. You feel like you are drowning, because you are drowning. :p

But there ain't much point in thinking what could have been done or said differently, if you don't drown you'll eventually learn how to swim. :D

In your case though, if you don't get a positive reaction from a guy it's only because he is trying to collect his brain from the floor in order to understand how this gorgeous girl was talking to him. :eek:
 
I'm a natural introvert. It took working some (admittedly horrible) sales jobs in my youth to learn that you don't get what you don't ask for.

Surprisingly, generally the worst thing that could happen is that you don't get what you want - and that was already the situation to begin with.

Sure, there's the risk that someone's going to cut you down or say something cruel, too - but in that case, you've learned what kind of person they are, and you can be happy that you DIDN'T get with them.

And all that said... I'd have a hard time picturing a man saying no to you unless he was married or otherwise attached, gay or asexual, or a member of the clergy in one of numerous backwards religions.
 
a man saying no to you unless he was married or otherwise attached, gay or asexual, or a member of the clergy in one of numerous backwards religions.

My beer is on that all of that and it's still fifty-fifty chance he says yes.
 
I am very much an introvert, but I’m trying to become more social and less.. reserved. As weird as it sounds, one of my goals for this year is to take initiative and approach a man for the first time. I’ve never done it, due to fear of rejection.

First time I asked someone out was in college, back in the time when dinosaurs walked the Earth. ;)
Like you, I kind of kept to myself and wasn’t very outgoing - fear of rejection was high for me.
But if I could go back and talk to my younger self, I’d tell him don’t even waste your time worrying about it.
(And invest in shares of Apple and Google) ;)

In your case though, if you don't get a positive reaction from a guy it's only because he is trying to collect his brain from the floor in order to understand how this gorgeous girl was talking to him. :eek:

Seriously though Hana, you are amazing and you have nothing to fear. I agree with @MikeH , the only thing you have to watch out for is slipping on the guy’s brain juice. ;) Any man would be lucky to have you in their life. :)
 
Take a little time . Drink your first drink and carefully check out who's checking you out. Somebody definitely will be. Then smile at him for one second. One second. Look for his reaction. If he acts mean ignore him like the pile of useless dog shit he is. If he looks shy like he doesn't know what to do then approach him. Use any line - "Didn't you work with Frank Sinclair at Morgan Stanley?" let the conversation flow from there.
 
A little more...

A woman once picked me up - back when I was young and good looking - by standing with me and some buddies drinking, waiting until I finished my beer at which point she said "Can we go now?"

She wasn't even my type. But we hooked up and saw each other when things worked out.

That was 1992 - and we're still in touch.
 
You are so young. 20.. I was a completely different girl at that age. Don't compare yourself to people older than you because contrary to what magazines say age can bring you a lot of positive things.

Best way to overcome shyness, introvert tendencies, anxiety, etc is to throw yourself into life. Things can go awkward, but see it as part of a bigger plan. When I was a child my dad took me and he threw me into the sea. I flapped my arms and legs and realized I was able to swim. I was shocked and very scared, but now I know why he did this.

And never ever do things you're not comfortable with to please other people. You're worthy of love and respect.
 
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I was scared to death of rejection when I first start approaching women with social intentions (not sexual ones, the *only* thing I knew about sex at that time was that I wanted some very badly), and I invariably got rejected for quite a long time (by my standards at that age).

What eventually worked for me was when I came to think of it the way I now think of buying a lottery ticket. I don't expect to win; I go in essentially certain that I will lose the price of the ticket, but that doesn't bother me at all because the cost is so small. However, if I ever win, the gain will be huge, so it is amusing to play.

Once I started thinking of approaching women with a similar attitude, my "batting average" quickly went from zero to respectable. It probably also helped that my voice got deeper and that I grew taller than most of the girls my age. :D

What you absolutely should not do imo is screw up all the courage you can muster and force yourself to approach a guy you feel you "must" have with an "I'll die of embarrassment and disappointment" if he doesn't respond well attitude.

Summary, don't be confident and don't be desperate. Just do it without over thinking it...without thinking about it at all to the extent possible.

Alternatively, save up some money and contact @Synapse for lessons. :D

-Ww
 
I have always been timid and shy [I still prefer books and computers than people]. First time I tried to ask someone out, I was 17. She was my classmate in uni. She was a year younger than me (she actually looks like you @MissInsomnia, just with eyeglasses. Her dad is part spaniard. and her mom was part chinese--that probably explains the similarities in looks)...it didn't turn out so well. She was the first person to break my heart.

The strange thing is we became best friends. Maybe, I was too obvious that I was very much into her before I tried to ask her out. That must have spooked her. A few months after I tried to ask her out, we figured out that we had some things in common (we are both bookworms and into drawing. But she is a more talented artist than me).

We still keep in touch to this day.

In retrospect, I should have tried to get to know her first then asked her out. I will just have to live with what could have been.
 
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i dont approach too often. a lot of the time the woman makes initial comment or question and i pick it up from there ^.^

I dont remember my first cold approach however in general my trick is to usually find something in and around close proximity to remark on, suggest, point out, ask about. AND do it with a smile and half laugh. You come across as fun casual and not creepy.

Thats the best imo..its harmless, you dont come across as a sleezy pickup artist, there isnt ever a rejection and it gets them talking.
 
I'm a full-on introvert and I've been asking girls out since I was in elementary school. That's little to do with it :) . Introvert is how you recharge. Meaning you should be coming out of your cave at 100% charge and as soon as you start talking people your power quickly starts to go down. I'm saying this because most people cannot change this quality about them, and I want to reassure you that introverts can knock it out of the park with the rest of them.

Before you even ask, you've gotta know the signs if there is mutual interest already, right? Even if there's like a 20% chance, I take that as a GO

As for getting rejected, you'd be surprised how quickly you get over it when (a) you didn't invest a lot of time thinking about the consequences of getting rejected and (b) just ask in the most frank and silly way possible. Don't make it too serious or it's hard to walk away from a no with your spine.

Think of the activity beforehand and set it up. "I wanna go to X with you, clear your calendar! If you say no our friendship is over!"
 
By the way I realized I didn't explain how I approach guys. I approach them physically and then go for a kiss once our eyes lock. But then again I'm a bit rapey. So far no one has slapped me or pushed me away and said "ohmeygewd why did you kiss me"..

haha please be mindful :) if a guy's just trying to wrap up the night and get back to his wife and you've locked a lipstick footprint then you've condemned him
 
For most of my life I did not realize I was an introvert until after having a discussion with a friend about what I would rather be doing than *insert group function's name here.* Once the realization hit me, somewhat of an emphany, I was dragged into an extended period of self introspection. I started inventorying life experiences and specifically regrets that were impacted by my introversion. Among those were of course my fear of rejection from women. I am not sure I have ever asked a woman out, even to this point in my life. Most of my encounters and relationships were intiated by others, girl, woman, or a third party (p4p excluded and even that has its own anxieties attached) rather than from mustering the courage to do so of my own volition. However, I have come to the conclusion that introversion has nothing to do with my fear of rejection, but rather it's protecting my pride and ego.

I am my own fan club, never have I ever not believed I am incapable of doing anything I set my mind upon. However, I have always increased my odds of success by controlling variables to stack the deck. And therein lies the difficulty, I know I am not an attractive individual and I recognize that fact. Therefore I am afraid of injuring my pride via the obvious rejection I will receive, most likely the "I would just rather be friends" response, which can only be taken in the most harshest way possible (not interested in you, but I also pity you too much to be candid).

Could introversion stop someone from asking someone out, yeah maybe. But I would think it would depend on the setting, but I do better one-on-one, and since it only takes two to tango, well. For group activities I don a persona, who would want to date my persona?

But Hana, seriously, if it is pride, then you fail to recognize what many of us know, you are a breathtakingly beautiful woman and person. I would have to echo previous comments, they guy (or girl, sorry had to have a little fantasy, it's my post afterall) has other issues that have nothing to do with you. My goodness, if you had approached me at your age when I was a much younger man I would have been floored and looking for the hidden camera.

Perhaps if you still feel it is because you are shy, try to control the setting to an environment that makes you more comfortable. And please accept that if you get rejected, they have their own issues, and you are probably better off not learning first hand why they are such idiots.
 
@JackB the good thing of course is guys can be ugly and still score. Girls seem to be way better than guys in looking the person and ignoring the outside.

But I just now realized what should have been the obvious first reaction to OP. Of course telling which pub you are tonight and then promising to be a practice target for easy pickup.

Just goes to show how impossible is the thought she would not be able to pickup anybody she wants anywhere.
 
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I only approached the girls who looked interested and it seems like my interpretations of the signs were right :D
 
I like the dichotomy of « asking someone out / picking someone up ». It’s actually two very different things. I asked someone out at the tender age of 5 and stole a ring from my mum to give it to her. The funny thing is that she was the daughter of the local head of police, which even to this day makes my mum laugh hysterically. Yes , you can be madly in love even at kindergarden.
Picking someone up is much less romantic...
i dunno, i must have been 16, half-drunk, and it didnt go very far
 
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haha please be mindful :) if a guy's just trying to wrap up the night and get back to his wife and you've locked a lipstick footprint then you've condemned him
That's why I only wear nude lipsticks.
I'm not a home wrecker. :D :)