Okay boys, it's almost Valentine's Day. Time to man up and ask that pretty girl you've been eyeing out on a date! C'mon, you can do it!

I know, I know. It's scary. What if she says "No"? What if she's not interested? What if she doesn't even know who you are?

Well, here's what you can do.

There's a mantra I often repeat to myself. "It's better to try something and fail at it, than to walk away and regret never having tried at all." This mantra has served me well in business, in life, and in love.

Translated to dating, it would read:

It's better to ask a girl out and get rejected, than to walk away and regret never having asked at all.

Just imagine how you'd feel, twenty years from now, seeing the girl of your dreams just as a friend and nothing else. Maybe she's dating, maybe she's married. But since you never asked her out, you never found out how she feels about you. You never found out what could have happened, if only. What Ifs plague your thoughts and haunt your dreams.

Agonizing, isn't it? The regret is always worse than the temporary feeling of rejection you'll face, since regret can last a long, long time. Your body can handle the bee sting of rejection. But having your heart cleaved by the sword of regret is a deep excruciating pain.

With that said, here's how you ask a girl out:

  • Ask Her Out

    Well, duh. There's really no magic to it. You go up to her and ask her out.

    Ask her if she wants to get dinner tonight, a musical this weekend, or a ball game next week. Or if you want to play it more low-key, make it a coffee.

    What's important here is that you make sure she knows it's a date. Make sure she knows you're interested in her and want to get to know her better. Don't play the friend card with the hopes of turning the dinner into a date later. You'll just fill her with confusion and a sense that you don't really like her. At best, she'll put you on her Friends List. At worst, she'll put you on her Wimps List.

    You don't have to declare your love for her or anything that dramatic. Just make sure she knows you're interested in her.

I know, I know; easier said than done. What if you're paralyzed with fear every time she comes near? What if you're pretty sure she's more interested in shoes than you? What do you do?

If nervousness, sweaty palms, and a clenched throat are your adversaries, consider a relaxation instrument. Like yoga, meditation, or even alcohol (otherwise known as liquid courage). Get yourself calm enough, and brave enough, to go up and ask her out.

You could also tell your friends about your intentions. This isn't so they'll ask her out for you; immature tactics like that rarely work out. This is so they'll push you. Sometimes we need the encouragement of good buddies. A cheering squad on your side can pump courage in spades.

If she doesn't even know you're alive, letting her know you like her is a great way to change that. Sometimes just the flattery of being liked by someone can make us like that person, even a little bit. You can play it smooth and do nice little things for her to let her know you're thinking about her, or you can be overt and send her flowers and chocolates.

(Stop at following her home and calling her every night though. A disarming guy doing sweet things is persistent. A threatening guy studying her every move is a stalker.)

And what's the worst that could happen? She could reject you and you wouldn't be dating her? Well, you're not dating her now, are you? So what did you lose? Nothing!

Finally, if she's a good catch, chances are that if you don't ask her out, someone else will. Just like good parking spots, good catches don't stay available forever. If you see a window of opportunity, take it now, for it could slam shut tomorrow.

So what are you waiting for, stud? Man up! Ask her out! Do it now, so you don't regret never having asked at all!

. . .

What advice would you give a guy who's afraid to ask a girl out?