NEWS: The Gentleman's Guide to Asking Out A Lady

CULTURE: The Gentleman's Guide to Asking Out A Lady

Good afternoon, Gentlemen.

Please. Come in. Sit down. Can I offer you a drink?



Perhaps a nice ale?



Gentlemen . . . We need to talk. I have been hearing from the ladies that some of you still don’t know the proper etiquette for asking a woman out on a date.

This is a serious issue, and I cannot allow you to continue on this course. If you continue on this course, the only people you will have left to kiss will be each other. And some of you simply aren’t pretty enough to be gay.

If I may, gentlemen, I have asked my charming assistant, Steffania, to join us, to act as a model for our scenarios.



Hands off, gentlemen. She’s taken.

Let us proceed. Steffania, if you please.

First thing first, gentlemen. I would like you to look at Steffania. Pretty, isn’t she? Well, I have a surprise for you.

She is a person.

She is not a mythical creature. Nor is she a statue on a pedestal. She is a person. She has good days, bad days, days when she wants to do nothing more than watch TV all day in her pajamas with a bag of chips and a jar of salsa. She thinks, feels, reacts, and understands life in much the same way you do. This is very important to keep in mind when approaching a strange woman to strike up a conversation.

You are going to need some good observational skills. Say you are looking (NOT ogling) a woman in a bar. How is she sitting? Where are her eyes going? Is she looking at people as they go by, or is she staring down into her drink? Is she sitting hunched over, as if presenting a shell to the room? Or is she leaning back, with her shoulders open and her head up? Is she slamming down her drinks, or is she playing with her glass?

These are all important things to pay attention to. If she looks like she does not want company, do not approach. She is not there to meet someone, and bouncers will act in her favor with just a wave of her hand if you persist where you are not wanted. It does not matter if you think she is the future mother of your children, at that particular moment you are something nasty that she stepped in.

Once you have determined that she is willing to converse, make your way up to her. But again, be wary. Is she there with a group of her friends? Is she seated alone at the bar? Is she seated at a table for two and keeps looking at her watch? None of these are insurmountable obstacles. But, keep in mind, if she is out with friends, she is there to have fun with them. She might welcome your attention, but there is also a good chance that she is more interested in doing tequila shots with her friends than meeting someone new.

Now, you have gotten close to the woman. It is time to start with some non-verbal communication. Steffania, if you please. Watch, gentlemen, as I catch her eye and give her a friendly smile. Not a leer, not a cocky grin. A smile. Note how she reacts. She smiles back at me as she assesses me and determines that I am not a threat to her.

If she does not return your smile, gentlemen, I would suggest backing off. You don’t know why she isn’t returning your smile, and 999 times out of 1000 it will have absolutely nothing to do with you. Don’t take it personally. She is not being a bitch. She just doesn’t want to be bothered.

Once she smiles at you, you have permission to approach and start a conversation. Now, I cannot stress this next part enough.

Do Not Use A “Line”! Don’t ask if she’s tired from running through your mind all day. Don’t ask if it hurt when she fell from heaven. Certainly do not flick a drop of water on her blouse then suggest that she should come home with you so she can get out of those wet clothes.

There is no such thing as a guaranteed line. In fact, there is only one thing to say that isn’t going to make you look like a complete and total ass.

“Hi. I’m _________. How are you?”

That’s it.

Now comes the hard part. You’re actually going to have to talk to her. Keep it light, keep it upbeat, and keep your eyes on hers.

If all goes well, the two of your will share a nice conversation. You will learn something about her personality, she will learn something about yours, and if the two of your are compatible, it is time to move on to the next step: asking for a date.

Do NOT ask if she wants to “get together sometime and do something, maybe?” There is a very good chance that she is busy “sometime” and did “something” yesterday.

Be specific.

Remember that nice conversation you just had? Take a few hints from that. If you were paying attention, you will be able to think of some activity that will interest both of you. Ask her to join you for some specific activity on a specific day and time. A concert? A museum? A new restaurant? A walk in the park? An art gallery? A roller derby match? Whatever works. Just keep a few things in mind:

1. The activity should not involve removing clothes;
2. The activity should be something BOTH of you enjoy; don’t fake it.
3. The activity should allow time for the two of you to talk further.

Once you have agreed to meet at a later date, it is time to retreat. Exchange phone numbers, tell her you had a nice time, and leave the premises.

There. You have a date.

Now, I have to warn you. This will not work with every woman, for the very simple reason that all women are different. But if you modify it for the situation and remember some very simple rules:

1. Be Polite.
2. Be Respectful
3. Be Honest

Women are people. Real people. They’re not some sort of mythical creature, sent to frustrate you in your quest. Most do like nice guys. But what they like more is confident men. Men who know who they are, know what they want, and don’t give a damn what anybody thinks about them.

These tips are only for trying to meet someone and potentially start a relationship. It is not for one night stands. But then, gentlemen do not engage in such activities.

Now, if you will excuse us, Steffania and I have a date.

Shall we, my dear?

I love this series.

Better then the first, I thought! Bravo!

At What point do I display my Mating Plumage?

You have a faux-hawk?

That ale doesn't look that nice. I mean, what kind of pour resulted in that kind of misshapen head?

A gentleman wouldn't point that out.

A gentleman would offer me better beer.

A gentleman would be grateful for something freely offered. Besides, you could have the scotch instead.

too much work. i'll just stay single.

I know I'm one of the ladies that you're writing about, but damn if I couldn't go for one-o-them ales.

but that -let me get you out of those wet clothes - line is one of my favorites to use.
true.

Well done, again, sir. And you're quite right. That next bit after the "Hi, I'm..." is always the difficult bit.

If I may request one expansion, your suggestions focus on the public house as a venue of introductions. For myself, I take my libations more rarely and in private company as often as public. For me and those like me who are more likely to meet compatible souls in a non-alcohol-mediated-venue, do you have any modified advice for how the conversation should be begun?

That's actually a nice, foamy crown and I would not turn it down.

It becomes easier outside of a public house, because the place often has some sort of common ground you can use to start a conversation. Bookstore? Talk about books. Coffeeshop? Talk about the people around you. Museum? Take a guess.

I wouldn't recommend approaching a woman at her job, as she is busy and has her mind on other things at the time. She might welcome the distraction, but you can't know that from the start.

Feel free, both of you. Just tell the bartender to pull you a glass from the AGS (Academy of Gentlemanly Studies) Reserve supply.

Good stuff

Well done sir. The politeness policy is the way to go. I appreciate that you shared just what needs to be shared so you're not just giving guys a Gentleman's Diploma so to speak. Take it from there men. Get creative and be awesome..... and thats a good head.... if when that beer is gone and there are foam lines all the way down the glass... thats a good beer... and a clean glass... and your bartender loves you.

Round cleared.

Welcome to the next level: Context free spaces.

The boss for this level:
Girl who just smiled back on the subway.

Bonus round:
Girl on the other side of the street who just glanced away and blushed when you spotted her checking you out.

You say this like it isn't every day of my life. I guess that's why I'm not at the bar getting picked up by gentlemen.

At that point, you're on your own. But I wouldn't recommend an approach in such situations. Too much of a creep factor.

And DO NOT HONK AT HER!!!

Good article, btw.

Drat! Now what am I supposed to do with this clown nose?