Austin Matchmaker


Top 5 Ways to Approach Anyone, Anywhere

IF THERE’S ONE skill that will catapult you in work, love and life, it’s the ability to know the top 5 ways to approach anyone, anywhere.  I’m willing to bet that the urge to approach someone new—a cute girl on the street, a professional hero at a conference, or a dude at a cafe who seems like he’d be a cool friend—struck you at least once this week. I’m also willing to bet that you let at least one of those moments pass, and decided not to take the leap. It takes a lot of guts to approach a stranger and start talking.

There are times when it’s act now or never see the person again, or when the strength of your feelings overwhelms you and compels you to act.

Think about all the things you do when you have a little time to fill on your own. Great places to approach anyone, anywhere are at coffee shops, gyms, museums, bookstores, grocery stores, or just standing in line. Once you look around, you’ll realize how many people are out there just waiting for you to say hello to them! If you’re thinking, “That all sounds well and good, but how?” I’m sorry to tell you there’s no foolproof formula, but here are a few methods I’ve seen work for me and other people in the past.  It is best if you are solo when trying out these top 5 ways to meet anyone,  anywhere.

  1. Use Humor

Showing you have a sense of humor is a real door-opener because it shows a willingness to be self-deprecating which can be very attractive.  When you approach someone anytime anywhere, a great opening line can be “Excuse me for interrupting. I can see you’re busy reading/working but you caught my attention so I thought I would risk public humiliation by introducing myself. My name is _________________ “ and take it from there!  Sometimes when you give strangers the opportunity to talk to you, they can actually be cool. (But you’ve seen hundreds of rom-coms, so you know that.) This is one of the top 5 ways to approach anyone, anywhere.

  1. Take a Survey

Everyone wants to feel smarter than a 5th grader so in the name of research, a survey is the perfect way to use as a conversation springboard.  When you approach anyone, anywhere, I would suggest asking something pertaining to being single.  For example, “what percentage of people at this bar are here to actually meet someone to date versus those who are just out to have a drink with friends?” It allows you to go up to anyone and just start talking… men and women! And you don’t have to worry about coming across as hitting on them. It’s all in the name of research! This is one of the top 5 ways to approach anyone, anywhere.

  1. Ante Up

Walk up to someone at a bar ideally and say “my friend and I are having a bet that whoever can meet 5 people the fastest owes the other one a free drink. All I need to know is your full name, your age and if you are single”. Then after you meet the 5 people circle back with whomever you liked best and take it from there!

  1. Make an observation

Pick something in the environment around you that you can comment on, like in a museum, ‘Isn’t that the ugliest painting you ever saw?”’ It’s something they can focus on, comment on, and it’s a non-threatening comment. Or at the grocery store, comment on what they are looking at for example in the cereal aisle you could say “life’s short, buy the Frosted Flakes—sure it’s all sugar, but everyone needs to eat like a kid now and then”.

  1. Ask for help

Ask a simple open ended question relevant to where you are at. For example, at a grocery store, “Excuse me, I’ve always seen that sauce and wondered about it. How can you use it? Is it very spicy?’ Or at a music store, say, ‘Excuse me, I’m just getting into ________ type of music. Can you recommend something?’

6. Be Upfront

This last strategy is the one that can make us feel the most vulnerable. It’s hard to put yourself out there and to worry about possibly being rejected. But when you feel like you have the most to lose, you most definitely have the most to gain. If you’ve had only brief interactions with someone you want to get to know better, it’s absolutely okay to share that you’re looking to meet new people and that you’ve really enjoyed the conversations you’ve had so far. This is one of the top 5 ways to approach anyone, anywhere.

Being direct about your desire to make new friends doesn’t have to be a big scary thing.

Casually let them know that you’d be happy to chat again or get together in a different context (e.g., “Hey! I really enjoyed our conversation! Any chance you’re open to grabbing a coffee sometime?” or “I actually just moved here and don’t really know anyone. I’d love to find a time to hang out and maybe go for a walk together!”). People are often far more receptive to this than we expect. They might even be relieved that you made the first move!

Before you go testing out these strategies, let me forewarn you that they only work with the right attitude. First of all, you have to be bold enough to accept that someone may very well respond to your flirtatious “hey” with “I have a girlfriend,” “I’m not interested,” or “I don’t know English” (it’s happened). You also need an open mind. Chances are, you won’t get a date every time you try. But if you commit yourself to having fun even if you don’t get a romantic connection, you’ll be wasting far less time than you’d spend scrolling through OK Cupid profiles or swiping right.

Potential dates are everywhere that you are, so don’t be afraid to strike up a conversation, make a comment, or ask a question when the opportunity arises. Ask for directions, ask someone if they have the time, JUST TALK!

In summary: we’re always one conversation away from our next ideal job, our next amazing business deal, and our next great love affair. Or we’re one conversation away from helping someone else reach theirs.