No man is defeated without until he has first been defeated within. - Eleanor Roosevelt
Question #64962 posted on 10/16/2011 2:06 p.m.

Dear 100 Hour Board,

How do I properly ask a girl that I like on a date? This may sound stupid, but I honestly have no idea how to ask a girl on a date unless she's one of my really close friends.

-small town guy without a clue


Dear small town,

First off, good job for wanting to ask out girls even if you don't know them already. That's one of the purposes of dates!

Here are some thoughts from Anne.

How NOT to ask a girl out:

  • Via text message, facebook chat, facebook message, twitter, or any other form of text-driven media.
  • On the phone (note—this may be acceptable in some situations, e.g. the girl is currently out of town and you cannot contact her in person.)
  • Ambiguously—without indicating a definite time, place, activity, etc. The girl should know that this is a DATE, and should also be aware if it's a double, triple, or group date or if it will be just the two of you. Actually using the word "date" is a good thing, because it means that the girl really doesn't have to wonder about what exactly just happened. 
  • In front of other people. This leads to awkwardness for both of you if she isn't really interested.

How to ask a girl out:

"Hey, would you like to go on a [group] date to [insert activity/event/etc., preferably not a movie if it's a first date] with me on [date, time?]"

"Hey, I wanted to go do [activity] on [date] and I thought it would be fun if we could do it as a date- is that something you'd be interested in?"


Basically, you want to tell the girl that you'd like to do something with her, specifically—preferably a specific something at a specific time, rather than just "Hey, we should go get pizza or something sometime." It doesn't need to be a big confession of your budding feelings for her, it just needs to be an expression that you're interested in doing something with her and getting to know her better. Don't make a big deal out of it, just go for it! 

Good luck in your dating adventures!

~Anne, Certainly


Dear Basil,

I'm just going to throw out my one pet peeve, if you are going to ask a girl out, give her some warning. Do not ask her to dinner the day of (or even the day before) and then be sulky when she can't (or, in my case, won't) go. I mean, really, it just looks like you don't have anything better to do so dinner with her is a last resort.

Other than that, I completely support Anne's suggestions and wish you all the best in your dating endeavors!

-Marguerite St. Just


Dear small town guy,

Okay, look. You've got a couple of opinions up there, but I'm here to tell you what's really up.

So, you like a girl. Good for you! Assuming she's not already dating me, here's how you should ask her out:

  1. Smell good.
  2. Walk up to her, preferably when she is surrounded by friends.
  3. Without saying a word, get one foot away from her and then...smolder. (At this point, you might want to shift your body weight to prepare to catch her, as she will inevitably swoon.)
  4. As you bring her back to her feet, whisper, "Dinner...7 o'clock...I'll pick you up," gently in her ear.
  5. Then, as you are pulling your face away, VERY GENTLY smooch her on the cheek. This seals the deal.
  6. Remember to actually pick her up at 7.

There you go, friend. Repeat a week later with her friends.

-Rather Dashing