We have spent quite a lot of time discussing the wrong approach to dating. And while there will always be plenty of mistakes to go around, we should not feel defined by our failures. If you’ve been a back-door-boy in the past, here’s  your chance to try the front door instead. If you have been settling for back-door-boys as a woman, here is what you’ve been missing out on.

Remember, the method determines the message. If all of the fearful, lazy and ignorant ways of boys are indicative of someone who uses the back door, then it makes sense for the opposite to be true of the front-door-man: he would be bold, diligent, and aware.

He is bold: He recognizes that rejection is a legitimate possibility, but that doesn’t stop him from asking. Why? Because she is worth it.

He is diligent: He recognizes that pursuing a woman requires considerate effort – especially with those who are not immediately attracted to him. He works hard to pursue the woman because she is worth it.

He is aware: He knows how to ask to be in a woman’s presence in a way that is both winsome and flattering without being sleezy, cheesey or over-the-top. He has taken time to learn how to approach the woman of his dreams because she is worth it.

So, as Nacho says, let’s get down to the nitty gritty.

Let’s say there’s this guy named Bob. He meets Sue at work and is quite taken with her. He quickly finds out she is single and decides to ask her out. Fortunately for us, Bob is a front-door-man so watching him will give us a great first-look into how to ask a woman for a date.

A few days after noticing his attraction for Sue, Bob decides he is going to go through with asking Sue for a date. So, he gets out his calendar and considers his schedule before asking. He finds a weekend that he knows he is free and thinks that she might be free as well. He has in mind the day and time of the date before ever approaching her. In fact, he probably has some alternates in mind too – just in case she isn’t free on the night he asks for.

Bob heads to work the next day, Wednesday, prepared and ready to ask Sue for a date on Friday night. He patiently waits for the end of the day and catches her just as she is leaving the office.

“Excuse me, Sue. My name is Bob, I work in accounting. We met last week during Larry’s presentation.” Bob is calm, confident and has a pleasant smile on his face. Of course he made sure to shave and dress nicely that day.

“Oh, yes, hello, Bob! Good to talk with you again.” Once Sue gives Bob her eyes, he makes sure never to look away from them. She is his focus – he wants to communicate that.

“Thanks, Sue. Do you have a minute?” Bob doesn’t assume that Sue has the time to stop and talk. He also does not assume that she actually wants to talk with him.

“Sure, I’m just walking to my car to head home. What’s up?” Bob is relieved that although she had the opportunity to move on she didn’t. He rightly takes that as a positive sign and decides to ask before circumstances change.

Calm and very matter-of-fact (because he knows he’s not asking for her hand in marriage – just dinner), Bob makes his request: “Sue, I really enjoyed talking with you after the meeting last week and I was wondering if I could have the pleasure of taking you on a date Friday night.  Would you like to have dinner with me?”

“Sure, I would like that. Thank you, Bob!”

“Great! You’re welcome. How about I pick you up at 7pm and we’ll go to a casual dinner?” Bob isn’t sure of when the next time is he will talk with Sue before the date, so he wants to make sure she knows what the date will be (girls like to know what to wear).

“Sounds good!”

Bob then wraps up by asking for directions to her house and for her phone number and then lets her go on her way.

Bob just knocked on the front door. Although circumstances will differ for each man, the basics will remain the same in any scenario:

  • He had a plan in mind before he asked
  • He asked about 3-4 days in advance
  • He asked her at the end of her day (not at the beginning or middle)
  • He gave her good eye contact
  • He paid her a compliment
  • He used the word “date” in his asking

Now, how should the woman respond? The man has done his part. He stuck his neck out. What if the woman isn’t interested? What if she’s not available, but is very interested? What does this look like from a woman’s perspective? We’ll cover that in chapter 2.5.


How does this sound? Any suggestions on how you would do it differently?

[Ladies, your input here will be most valuable for the men to hear. If this is the way you would like to be asked out – this is a great place to let them hear you say so.]