How to Approach a Charming Stranger and Ask Them Out

How to Approach a Charming Stranger and Ask Them Out

Not everyone gets the chance to fall in love with a familiar person. For most of us that charming stranger represents the person we want to be with and promises a romantic adventure that might end up with something lasting. At times a charming stranger might be coming your way or seated in a place close by. You might feel strongly that you’d like to see them again. Asking them out is the first step towards that.

However, having been rejected and embarrassed before the fear of being turned down makes us recoil to our cocoons and just watch the person disappear into a sea of humanity, mall, church, street corner or a building complex somewhere.

What if there’s something you could do? What if you could find some little courage and self-confidence would you go ahead with it? Of course once you start doing it you’ll realize how easy it is. Even if the lovely stranger turned you down you will be really happy that at least you tried. In fact, any chance you don’t take for whatever reason is a chance lost forever.

First things first

The first thing before you even open your mouth to say anything to the charming stranger is ensure that you don’t pass out as someone threatening. A smile works magic all the time. It shows you are interested, not a threat and definitely friendly. Once you smile and the person responds it’s time to move to the next step to avoid awkwardness that could deplete your courage and destroy a great chance to date someone attractive.

Start a conversation

Make a quick observation or statement related to something that makes sense of the context. If you’re in a diner, you could make a comment about their meals, or performance in a rock concert if that’s where you are. If on the street you could use the same to create small talk. It can also be about the weather. Use the context to speak about something general and end it with a question to the person about their opinion on the same. For instance you could say, “Love the way they play the banjo here. Do you think they offer lessons? I’ve one at home I’d love to play better”.

It can be a comment about their choice of fashion or accessory just to open the door for small talk. Most importantly, avoid crappy pickup lines. Most people consider them too cliché and insulting.


Once the stranger starts responding and you begin a conversation and you intend to see them again show courtesy and introduce yourself. You could say, “I’m Luke by the way.” You can leave it at that or ask “What’s yours?” Go ahead and offer to shake their hand. This point is very important. It initiates the first physical contact between you. You will also know automatically if the person is just being polite or there’s hope for something more. Do it with a big smile of interest on your face and let the person see you’re genuinely fascinated by them.

Know whether the stranger is already taken or not

It’s critical to know if your charming stranger is taken or not. Perhaps they’re married or in a relationship. It’s most important to know. You could ask the person directly whether they’re seeing anyone, married or have someone in their life. You could also go indirectly into the subject matter by saying something like “wow, that’s a lovely locket, did your husband/girlfriend buy it for you?” or “would your girlfriend/boyfriend mind if I buy you a drink tonight?”

Ask them out

Once you get an idea whether the person is in a relationship or not it’s time be specific and make the most of the moment. Ask your charming stranger out. Let the person know why you would love to know more about them and why you find them fascinating and interesting. Ask directly if the person would like to go out for a drink, dinner, lunch or just a date with you to know more about each other. Something like, “You’re so funny. I love your well-thought arguments and our conversation. Sure would love to meet you again. Would you want to go out sometime?

You can also specify a specific day, idea or date to go out and weigh their response. If it’s not possible to come up with a proper time for a future date offer to call them later and set it up. In fact, if you get their phone number it’s safe to assume the person is available and open to seeing you again.