How To Get A Boy To Ask You Out

Dating, Humor, The Single Life

I was surprised to receive a few emails from a younger audience since publishing my last article on getting a guy to ask you out. I made a solemn vow to address the discrepancy between attitudes and behavior in men and, well, boys (early twenties and under is my guesstimate). Some turbid introspection made me realize that an article may well need to be restructured for this purpose, so here’s my take — for what it’s worth…

(if you’re a little older I suggest checking the aforementioned article, linked above!)

Boys. Yeah, I know — I Used To Be One

If he’s young, chances are he’s never woken up on a curb at three in the morning with a headache, being rained on, wondering where it all went wrong (*clears throat*). You see — as unattractive and harsh as it sounds, episodes like these teach us to weather and deal with rejection. Young men are — in the main — very scared little pandas when it comes to girls, simply because they haven’t been slapped repeatedly in the face with their own heart. Once you’ve been through it a few times, it gets easier (still hurts like hades though).

This makes inter-sexual communication a mess, because while they may be intrigued, interested and excited by a certain girl, they may try very hard to not show it. Why? Exactly! They fear rejection.

Mixed Signals

While not every boy will fit the bill with regards to my rejection hypothesis, my experience — and that of my all-knowing male friends — seem to find that it is. Now how does the element of insecurity make someone interested, but scared, act? Unfortunately, it usually results in a constant royal flush of mixed signals. Which means he may stare at you constantly but avoid eye contact, or smile at you but not be talkative. Let’s look at some other signs he may be interested but is timid.

  • He’ll be very self-conscious about touching you. He may go out of his way to avoid contact, but won’t shy away from your presence entirely.
  • His feet and shoulders tend to turn in your direction around other people and single you out.
  • If he’s outgoing, he may tease you an awful lot.
  • He’s talking too much, or too little. Basically, he’s acting very differently with you than he does with his friends.

Checkmate. But Why Isn’t He Asking Me Out?

While it may seem obvious to you that you are sending him signals, it may not be obvious to him. We men are quite dense when it comes to deciphering body language, we need you to dumb it down a little. I was quite popular with girls in high school, but only realized it ten years later! My suggestion is to drag fun into it, and a sprinkling of boldness. You needn’t do anything over the top, but holding eye contact and smiling warmly (don’t hold it too long, 1-2 seconds is bang-on perfect), touching him a great deal, laughing at his pathetic excuse for humor, and making a show of listening to his drama-queen rants, will definitely help him muster the courage — if he is actually interested — to ask you out.

But there’s some potentially bad news to consider. Sometimes, guys just like the attention. Afterall, even if you aren’t interested in someone, knowing they are is a compliment. There is only one way to be entirely sure, and that is realizing that…

Girls Are Not So Different, Are They?

Some guys simply won’t ask you, no matter how interested they are. Chronic self-esteem issues can turn eagles into pigeons (if only they knew). Thanks to the brain’s incredible way of giving us evidence of anything we chose to believe of ourselves, no matter how ridiculous, they may never choose to entertain the thought that you dig them.

The only way you can deal with this scenario is by stepping-up to the plate yourself and asking him out, or giving up. Before you smirk and claim that it’s a man’s job, realize that it isn’t indicative of a person’s strength. Inexperience is usually to blame, chances are that a loving relationship will reveal the well of strength that resides within him. Consider also that he may be reading an article on how to get a girl to ask you out at the same time you’re reading this — what an impasse!

And There You Have It

How to get a boy to ask you out? Be open and honest, make yourself approachable or just flat out ask him out yourself! Always remember that rejection will make you stronger, and it happens to everyone now and then, it doesn’t matter who you are. If you do succeed, don’t forget to remind him down-the-line that you were the one with the balls at the beginning of the relationship. He’ll laugh and thank you for it!

And so will you!


James Nelmondo

James Nelmondo

James "the Unknown" Nelmondo is a self-styled relationship enthusiast, former infant, part-time dumper and full-time dumpee.

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