“Helping questions are great conversation topics because when a person helps you it forms natural bonds. When you help another person to figure what an item is on the buffet or locate the restroom, it lowers your defenses. For example, if you’re at the grocery store, ask ‘Do you know how to tell if this fruit is ripe?’ It makes you look open to learning more and will help the conversation flow naturally.” —Dawn Maslar, MS, author of Men Chase, Women Choose: The Neuroscience of Meeting, Dating, Losing Your Mind, and Finding True Love. These magic phrases can save any awkward conversation.
Compliment something other than someone’s looks
“Instead of complimenting something generic like their eyes, highlight something that shows their personality, like their purse or a book. This is simple, elegant, and great if you are interested in someone or anytime you want to boost their likability toward you for business or social reasons.” —Paul DePompo, PsyD, ABPP, psychologist
Bring up a shared interest
“Many people think they have nothing in common with a stranger but if someone is at a grocery store, restaurant or bar they are there for a reason—one which is likely similar to yours. You’re both there so you both share a common interest. Ask questions to find out what that interest is. For instance, ask about what their experience at that venue has been like or why they chose it.” —Shannon Battle, licensed professional counselor
Go simple… yet bold
“Give a genuine smile and say, ‘Hi.’ It sounds too simple but people are so used to other people staring at their phones that a simple smile and hello can be a very bold move. It shows the other person that you’ve noticed them and you’re interested in getting to know them better. And you’ll almost always get a hello back. (If you don’t, let it go. You don’t want to date a rude person anyway.)” —Suzanne Casamento, dating expert and the creator of Fantasy Dating
Ask for their honest opinion
“Asking ‘I’ve been really thinking deeply about something and wondering if I can share it, and get your feedback?’ shows your interest in the other person and solicits new and interesting information that is fun to discuss. Pretty much anyone will want to share their opinions with an interested party and they will think you are nice and fun to be with, as well.” —Melissa Orlov, therapist and author of The Couples Guide to Thriving With ADHD
Tell a bonding joke
“Jokes work well because they are disarming and work on a biological level. If a woman laughs at a man’s joke, he feels assured that she has a level of comfort with him. For her, laughing releases oxytocin, the ‘bonding hormone.’ These two things together create an opening for more conversation.” —Dawn Maslar
Give an out-of-the-blue compliment
“I always tell my clients to try out a compliment. It breaks the ice and these days it’s completely unexpected! You can test out doing this by just giving people walking down the street a compliment and see their reaction, most times people will give you a smile and possibly engage in more conversation. After all, who doesn’t like to be complimented?” —Stef Safran, a matchmaking and dating expert in Chicago and owner of Stef and the City
Get (pop) cultured
“Make a comment or joke about something big in pop culture that most people would be familiar with—something light, NOT political. If you need ideas look at what’s trending or are hot topics on Twitter or Facebook.” —Stef Safran
Ask a fake favor
“People love to help so asking for a small favor is a great conversation topic. If you don’t have a favor to ask for, just make one up. Ask the person you find attractive to help you reach something on a high shelf or hold something while you look through your wallet. At the very least you’ll end up with a fun story to tell your friends.” —Suzanne Casamento
Make them your accomplice
“This can be as simple as waiting in line at the post office and saying something like, ‘You ready to go rogue? Let’s start another line so we can get this thing going.'” —Shawn Schweier, relationship coach and founder of Alter Shift
Show your silly side
“Asking a question with a little humor is a great move. Say you’re in a grocery store, ask, ‘This is very important: What is the best apple ever? Granny Smith or Red Delicious?'” —Suzanne Casamento
Invoke Ikea or the Queen of England
“My favorite conversation topics are something relevant yet funny. My favorite at an event is ‘I just came here for the free Swedish meatballs, why are you here?’ If I’m meeting someone new, I like ‘You look really familiar. Did you and I attend the same private dinner at the White House with the Queen of England?'” —Nicole DiCristofaro, dating and relationship coach at InvitingRight.com
Use a self-deprecating line
“A self-depreciating line is a good opening when someone is engaging in a positive type task and you comment on it. For instance, ‘I’m jealous that you are so good at that!’. This can actually show confidence because you are not trying to appear like you’re awesome.” —Paul DePompo
Tell a really dumb joke
“My favorite conversation topic is to say, ‘OK, I’ve got a dumb joke, not a good joke, just a dumb joke for you.’ People are usually more receptive to dumb jokes because it doesn’t require much effort and they don’t have to worry about not getting it. Need an example? What does a fish say when it runs into a concrete wall? Dam!” —Hunt Etheridge, dating and relationship expert
Blow their mind
“Most people enjoy trivia, facts, and riddles and they’re also a good way to keep the conversation going over an extended period of time. You can drop in and ask someone ‘What are the only 3 countries that start with J?’ [Jordan, Japan, Jamaica] or ‘How many state capitals are west of LA?’ [Six. I wouldn’t believe it either until I saw a map] or ‘What starts with “e” and ends with “e” andcontains only 1 letter?’ [envelope]. Then circle back with them later to see if they have an answer. They’ll be thinking about it—and you—all evening.” —Hunt Etheridge
Get deep
“Try using a light philosophical twist to an opening such as when you see someone enjoying a coffee you can highlight the beauty in the moment. Say something like, ‘Isn’t this what’s it’s all about?’ This is good for getting to see if this person is open and up for talking without making it seem like you are trying too hard.
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