No two women are the same. Accordingly, when asking a girl out, the strategy that works on one girl might not work on another. Knowing where you stand with a girl that you want to ask out is of great importance; you're not going to approach a stranger the same way that you approach a female friend that you envision as more than a friend. Since there's no way of knowing when and where you're going to fall for a girl, I'll break it down by five situations you might find yourself in, and how to seal the deal in each one. Let's start with the easy ones, before getting into some of the more complicated scenarios.
1. Asking Out A Complete Stranger
Asking out a complete stranger might seem intimidating at first, especially if you don't have the aid of liquid courage (which I'll get to in the next scenario). But when you really think about it, asking out somebody you have absolutely NO relationship with is total cake. Think about the cost/benefit analysis. If you approach a stranger and she's not interested, you lose nothing, save maybe a shred of pride. If you approach a stranger and she is interested, you are #winning. If you never approach her, you lose by default. No real downside, big upside.
What to do: Just go for it, dude. Be confident. Be straightforward. Compliment her. Saying something as simple as "I couldn't help but notice that you're gorgeous. How does coffee next week sound?" can work wonders. Of course, get her phone number and solidify the date. Enjoy getting to know somebody new.
2. Asking Out That Girl You Met At The Bar
So you met a girl at a bar or a club or a house party. You had both been drinking. Maybe you danced for awhile, maybe you made out, maybe more. But you're still intrigued, and hey, you got her number! So how do you follow up a drunken encounter with a real date that shows her that you're interested? It's pretty easy.
What to do: Send her a harmless text saying something like "it was a pleasure meeting you the other night!" Odds are she'll respond saying something similar — it's just common courtesy. Then, play it cool for a day or two. At this point, she'll be caught off-guard when you do the following: call her. Call, not text. Tell her that you'd like to get to know her better...and in a more low-key setting. If you've already kissed her, be classy enough to do more than coffee. Lunch is ideal. If you're feeling good about the way things are going, I'll give you permission to use Ascher's Tried-and-True First Date Move™ — give her one sunflower at the date. Yes, one, not the whole damn bouquet.
3. Asking Out An Acquaintance/Classmate/Coworker
This could be a friend of a friend, the cute girl in your sociology class, or the secretary at your office. In any case, this is a girl you know casually and have a crush on. This is where it starts to get tricky, because if you get rejected, you still have to see her around. So, don't get rejected!
What to do: To avoid a potentially awkward situation, you want to start harmless here. Since you know this girl in some capacity already, play it cool. Just ask her what she's up to on a day she's likely to be free, and invite her to go to happy hour somewhere. Beer is preferable to a coffee date here, as you want to gauge her interest, and booze loosens everyone up a little bit. Most women I know are willing to at least get a free drink and give a guy a shot, and hey, you miss 100% of the shots you don't take. If it doesn't go well? No harm done, it was just a drink.
4. Asking Out A Friend
Getting out of the dreaded friend zone is delicate process, and you have far more to lose here than in any of the aforementioned scenarios; after all, if you like this girl, you don't want to get rejected and ruin your friendship simultaneously. Tread lightly, be honest, and keep your expectations in check. The reward here might be the highest of all, since you already know this girl well and you're still interested, but beware, the risk is also as high as it gets.
What to do: Be forthright and tell her you want to take her on a date. Make your intentions clear by asking to take her out to dinner; since you're friends, just getting drinks doesn't get the point across. Pick a nice restaurant, but nothing too extravagant — coming off as too romantic won't be a plus as she tries to gauge whether the potential for more than friendship exists. Nonetheless, be a gentleman — pull out her chair, buy her meal, and so forth. The best case is that she feels a connection too, and your relationship progresses at a new level. But you must also prepare for the worst case: that she wants to keep you in the friend zone.
5. Asking Out Your Ex
You're drunk or lonely or listening to too much Taylor Swift lately, and it dawns on you that you should ask your ex if she'll go to Valentine's Day dinner with you.
What to do: Nothing. Do. Not. Do. It.
