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Be the wind to your own sails and all that, but also let’s think about this a little bit.

3 Questions to Ask Yourself Before You Ask Out That Cute Stranger

How to Ask Someone Out That You Barely Know

Be the wind to your own sails and all that, but also let’s think about this a little bit.

By Alec Cudmore, St. Edward’s University


You wanted to ask her out, but it would have been too embarrassing.

You wanted to talk to him, but he got off the bus two stops ago. You wanted to make the move, but something held you back. Was it the fear of rejection, or was it because it would have felt rude to approach them?

There are a lot of beautiful, interesting people out there, but how are you supposed to meet them? How could you possibly think to intrude someone else’s life?

3 Questions to Ask Yourself Before You Ask Out That Cute Stranger
Image via TheLastFM

When people chicken out, are they being socially conscious, or missing out on a great opportunity to get to know someone? It’s tough to know the difference. Asking out strangers can be a nerve-wracking ordeal, but I’m here to tell you that it doesn’t have to be. At the end of the day, striking up a conversation with someone, finding chemistry and asking them out on a date is a perfectly reasonable thing to do. I’ve taken it upon myself to craft a few important questions to ask yourself before deciding to approach. Hopefully they will serve you well.

1. Where Am I?

So you think the server who just handed you your tuna sandwich is pretty hot stuff. That’s great. You want to ask them out. Sounds reasonable. The only problem is that you’re in the busiest deli in the downtown area, and the customers behind you are already piling up. Your current crush looks busy as hell, and is already ringing up the man behind you. You hastily try to scribble your own number on a receipt, but you know it’s just going to get lost in the disaster that is the front counter.

You’ve found yourself in a stressful environment, and I guarantee you it is in your best interest to just walk away. In your perfect world, asking out the pretty girl in the deli would be what brightens up her day. But this is a world where we go to work feeling sick, and have bad days. Sometimes, it’s just not the right time.

A lot of men seem to struggle with asking themselves this question. Dark, decrepit subway train? Sure, seems like a perfect time to go up to the girl and tell her she’s got great legs (not the best opening line).

My favorite is the old “chase you down in the street because they just HAD to tell you that you’re the most beautiful girl you’ve ever seen” technique. Many of my friends have experienced this. These gestures are intended to appear sincere and courageous—but why is it that they never seem to work? I hear about these guys, these stories and they just disappear. It never transforms into some kind of amazing love story.

My only conclusion is that context really fucking matters. The world is filled with complex people who all have loads of stuff to get done. When you meet someone and find them particularly breathtaking, you tend to dehumanize them. You idolize them, and then forget that they aren’t a goal to be achieved. They’re a person. The server at the deli has a lifetime of memories and anxieties just like you. You are not going to just waltz in and change their life with one question, and the fate of the world doesn’t rest upon whether or not you ask them out. It can honest-to-god wait, if you really care.

So, to all men chasing women down in the street—just stop. You think you’re doing them a favor, but you’re really just serving your own ego. You really just want attention from the pretty girl. Stop and ask yourself where you are and why you’re doing what you’re doing.

2. Have We Engaged in Actual Conversation?

We live in a society where dating apps eliminate a lot of the mystery. When two people meet online and then meet at a coffee shop, oftentimes they already know there is an attraction between the two of them.

But I’m talking about the real world right now, the jungle of love, where you never know where you might just bump into someone you’re crazy about. Where the mystery is still very alive and there is absolutely no telling what’s going to happen. In this world, there are no dating profiles. There is no Facebook stalking. Everything you know about the person depends entirely on your ability to have a conversation.

So you’re thinking about asking out the girl you just crossed paths with at the bookstore. She’s cute, she seems to be interested in books just the same as you and you’ve had way too much caffeine. Before you do it, ask yourself one question: How do we know we even like each other as people? Behold, this is where the magic of conversation comes into play.

Talking to someone is how you figure out if you want to spend more time with them. I promise you, people are not as closed off as you often like to think. When you meet someone you are comfortable with, you open up. If starting with “You’re perfect in every way” or “Can I take you out sometime?” seems to result in more uncomfortable shrugs than enthusiastic smiles, it’s time to start thinking in a new way.

The next time you’re trying to come up with a cool pickup line, try just talking to them. Conversation lays the foundation for something that actually matters. If they don’t warm up to you, it’s probably not going to work out. Again, people are not prizes to be won. They’re allowed to not like you back, and you need to learn to be okay with this. Trust me, it’s not always easy. But it’s a valuable lesson that’ll make you happier in the long run.

3. Is There a Reasonable Chance I’ll See This Person Again?

Although I believe considerate thinking and meaningful conversation are the cornerstones of a beautiful romantic relationships, behind every duo is a singular moment in which someone decided to put themselves on the line.

Regardless of chemistry, context and mood, there is a moment where self-esteem is risked and hearts stop.

But does that have to be this instant? Is this really the time?

I’m not saying you need to second guess yourself. If you believe there is something special between you and another person, I can’t possibly tell you otherwise. But one must always take into account whether or not there is a true urgency. If there is a chance for you to see this person again, that gives you ample time to consider things. If things don’t have to happen this instant, it’s probably best that they don’t.

This doesn’t mean wait until you die of natural causes. It also doesn’t mean simply waiting a few minutes. But consider the foundation that can be built before throwing it all out there. If there is time, take it. Get to know them a little more. Encounter them a few more times. It’s a lot easier to agree to go on a date with someone you’ve gotten to know at least a little bit.

And of course, if you find yourself in a situation where it just might be your one chance, I say take it. Just do it in a polite way. If they say no, be nice about it. It’s a normal thing to ask someone out. Anyone who makes you out to be some sort of weirdo just for asking is a jerk (unless you ask them out in some insanely creepy way). Be a kind and courteous person, and I promise that you will meet other kind and courteous people.

You may even get to meet them for coffee later.

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