Conversation Topic: Make a bet

Conversation Topic: Make a bet
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“Walk up to someone and tell them you need them to settle a bet between you and your friend. For instance, say ‘Can I get your help with something? You see, my friends and I have this bet going on and we need an outside perspective. My friend says that the moon is its own planet. I say that the moon isn’t its own planet.’ Now, obviously, the moon isn’t a planet. Everyone should know that including this stranger you just asked. But it gives you a great in to start a conversation.” —Chris Seiter, author of Ex-Boyfriend Recovery

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Conversation Topic: Offer to help them

Conversation Topic: Offer to help them
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“Being helpful is always a great way to get a person’s attention, especially when they are struggling to do something or seem overwhelmed. The one thing people always enjoy is relief but you don’t want to add to their stress or come across as creepy. So try something simple like offering to hold something for them.” —Alexis Nicole White, author and relationship expert.

Conversation Topic: Disarm them with your vulnerability

Conversation Topic: Disarm them with your vulnerability
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“Sometimes the quickest way to make another person comfortable is to be vulnerable yourself. At a cocktail party? Tell the person next to you, ‘I don’t know a soul here. It’s so hard to talk to strangers.’ On a flight? Tell your seatmate, ‘Flying makes me a little nervous.’ People are more likely to connect with you if you are real, authentic, flawed like the rest of us.” – Jacqueline Lewis, founder of the World Gratitude Map, a crowd-sourcing project and online map that encourages users to document and celebrate the good things in life, and author of Life Begins at the End of Your Comfort Zone

Conversation Topic: Be brutally honest

Conversation Topic: Be brutally honest
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“I find that being honest and cutting to the chase is best as it doesn’t waste anyone’s time. This may sound too bold but it’s worked great for me over the years. ‘Hi, my name is Alan and I have to let you know upfront that I have absolutely no interest in being added to your stable of purely platonic male friends in the near future. For me, it’s romance, sex, or nothing.’” – Alan Roger Currie, author of Mode One: Let the Women Know What You’re Really Thinking

Conversation Topic: Tell them their celebrity doppelganger

Conversation Topic: Tell them their celebrity doppelganger
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“I tell my clients to think about a celebrity that the person resembles then approach the person and say, ‘Did anyone ever tell you that you look just like Sophia Vergara?’ This approach is always effective because it seems genuine, and the person on the receiving end will blush, lighten-up and say thank you. Because you will now have shifted that person’s energy to one that’s illuminating and positive, it will act as a great lead-in to the rest of the conversation.” – Tom Kersting, co-host of A&E’s Surviving Marriage and author of Disconnected: How to Reconnect Our Digitally Distracted Kids

Conversation Topic: ‘Cheers’ them

Conversation Topic: ‘Cheers’ them
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“If you are in a bar and looking for an excuse to talk to someone, just go up and raise your glass and say ‘cheers!’ This is effective because it’s non-threatening, polite, and will most likely be reciprocated.” —Laura Bilotta, matchmaker and founder of Single in the City.

Conversation Topic: Size them up

Conversation Topic: Size them up
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“People love to be seen as useful and if you ask someone interesting for advice, you’ve got an instant conversation starter to boot. For instance, if you’re shopping ask them what they think of a colour or a fit because the person you’re buying for is about their size or you want a man’s or woman’s opinion.” —April Masini, relationship and etiquette expert and author of the Ask April advice column

Conversation Topic: Ask to share their Uber

Conversation Topic: Ask to share their Uber
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“With the advent of ride-sharing services, it’s become easier to get from one destination to another so if you spot someone interesting on their phone trying to hail an Uber or Lyft, offer to share a ride if you’re heading the same general direction. Sure, it might take a little longer to reach your destination but it’s a great way to have a conversation. At the very least, you’ll both save on the cost of getting to your destination.” —Brandon Wade, relationship expert and CEO of several dating sites

Conversation Topic: Plan a dream holiday

Conversation Topic: Plan a dream holiday
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“Ask someone ‘If you got a free ticket to anywhere in the world tomorrow, where would it be?’ This line works for both in person and online conversations. There isn’t anyone on this planet that wouldn’t take a free ticket and it’s a great way to learn about them. Are they adventurous? Would they rather stay in the country? Follow up with ‘What else is on your bucket list? and share travel stories.” —Marcie Rogo, co-founder of Stitch.net

Conversation Topic: Scare them (just a little)

Conversation Topic: Scare them (just a little)
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“One of my favourite conversation starters is asking ‘What was your childhood pet?’ It immediately takes the person back to their childhood and may lead to them sharing other information about their early life. Then I follow up by joking, ‘You know that you just gave me the answer to one of your online security questions, right?’ People usually laugh because it’s true, often launching into a conversation about other common security questions, online identity theft, mistaken identity or some other all-too-common modern woe.” —Jenny Korn, PhD, scholar of identity at the University of Illinois at Chicago

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