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Why Don’t You Ask Her Out?

My dear Jack, you’ve got to summon up courage to ask her out. You’re going to die in silence wishing for her if you don’t summon the courage to ask her out. Granted if she says no it’s going to hurt, and damage your pride a bit, but what if she says yes! You keep dancing around her, circling like a wagon in a Western B Movie, imagining all sorts of scenarios in your head. You’ve seen her going down the aisle with you, even seen her having a baby for you. You’re a couple in your dreams. But dreams don’t produce a wife. And all the desire in the world will not produce a marriage. Ask her out. If you don’t bite the bullet and ask her out, you’ll be friend-zoned. She’ll be the wife you never had. You don’t want to watch another man take her, do you? You’ll have regrets. Right now you’re like a sub on the sideline getting ready to come on the pitch as the referee is about to blow final whistle. If she says no, laugh over the whole thing with her. Make fun of yourself. Continue your life. What else are you going to do? And she may change her mind later – who knows these things! But if she doesn’t, you have your life to live. Seek another.

What I suspect is that you really don’t know how to approach her. Not many men will admit that. It’s anti macho. I’ll pretend I’m not giving you a few pointers in this mail. Let’s keep it between us. (Wink!) Your greatest asset is your sincerity. Approach her sincerely. There’s something about sincerity of heart. Sincerity says, I really don’t know how to say this but I’d really like to ask you out. Would you like to go to the movies? If not that at least compliment her and just have a conversation. Ladies love compliment. There must be a reason you want to ask her out. Obviously you consider her attractive. Just tell her so. Sincerity. Forget “the game” – all that trying to talk smooth. At a certain level, it’s actually childish. Just tell her the truth. If you do all that funky stuff and she agrees, know she just wants to have fun. It’s not really the artificial jibe. It’s because she already likes something about you, had made up her mind on the possibility before you came.

Women are always ahead. Truth is, it’s the women who date us not the other way round. They just make it seem so. All the toasting in the world will not make her budge an inch if you don’t fit into her strategic intent and pursuit. Women are always miles ahead of men when it comes to the toasting thing. They just wait for us at the bus stop. She knows if you’re preparing to ask her out. And she has her answer ready. It’s not your proposal that elicits the answer. She can only be blindsided if she has her eyes on someone else. A woman thinks miles ahead. By the time you’re making your move she’s already made her determinations. Even if she drags it out. That’s a game. And if she wants you, whilst you’re still planning first date, she’s already planning wedding anniversary. Sit down there! So just approach her. Compliment her in the most natural way. Tell the truth about her look, something you admire. “I think you’re such a beautiful woman…I think you’re a wonderful person…I admire your talent…” Whatever! Just be sincere.

What makes us want someone is a combination of so many factors, it’s not just looks. Now, what makes a woman want a man is a combination of factors too. And most of the time it’s not what men think. Some of those things can’t even be formed into words. She just knows the man for her. If you can’t do a fancy date be honest about it. “I’ll like you to have Coke with me” should do for honesty. If you blow half your salary for the month on a date you’re not going to be able to sustain the relationship. So be honest even with yourself. Cut your coat according to the tape measure of wisdom. You want to somehow market yourself on that date. But you can’t be blatant. That’s too aggressive. She wants to know you’re a serious guy, that you’re not just looking for thrills and frills. A woman who wants to marry has no room for thrill seekers. Only serious guys. Doesn’t want to be confused with amusement park. She wants to know you’re going somewhere, that you have drive and ambition. That you have a plan. She can sense it. She wants to be sure you’re dependable. She wants to know you care, that you’re a nice man, a kind-hearted fellow. She wants to know you can both get along, that there’s a chance somewhere. She wants to be sure she can be happy with you. She wants to know you respect her. And that you love the whole of her, not just fascinated with feminine attributes. It’s why you sometimes hear beautiful women say they appreciate someone who truly values “me not just my body.”

She wants to know a little bit about your background – your family, your parents, where you’re coming from. She’s assessing whether she can handle your family set-up, whether it’s healthy and conducive to happy marriage. She wants assurances on many levels. And that’s your job on that first date. Or you won’t get a second. Just be yourself. Don’t try be proper and fastidious, you’re going to be clumsy, artificial. Like someone acting a script. You’re wise to allow her do her share of the talking. Have a conversation. She won’t feel satisfied deep down otherwise. Just have fun! There’s something called fun. Enjoy her company. Let her enjoy yours.

Now, be a gentleman after the date. Take her to her house or put her in a cab. Ask her to call or text you when she gets home. That you just want to be sure she got home safe. Shows you care. Now, I know your generation splits fares but I’m not sure you should be splitting the bill with a woman you invite on a first date. Even if she volunteers and you’ll really appreciate her input I’m not sure it’s wise to take money from her on a first date. Romance is very old-fashioned despite all our modern modifications. There’s something old in all of us. And please don’t ask her for transport fare after a date. Not sure you’ll get another date after that. You cheapened yourself. When she tells her friends about that you’re going to hear things like, “You must be kidding!… Don’t tell me he asked!”

If she had a good evening, chances are you’ll get a second date. And it will aid her decision-making. She has a lot to think about. She’s going to run the whole evening through her mind, cooperate with her emotions. And please when you get home, be kind enough to tell her you had a good time and that you enjoyed her company. That’s actually your opening gambit for a second date. Unless it didn’t go well. If after the first date she refuses to pick your calls or reply your text… Well, you’ve got your message. Move on. But we won’t know if we don’t ask her out, would we? So summon the courage. Ask her out.

Your mentor, LA

© Leke Alder |

For related letters, search for Sincerity, Toasting A Woman, The Girl Of My Dreams, at

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Tags : Value, Courage, Attraction, Confidence, Dating, Sincerity, expressiveness

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