13 Foolproof Ways to Start a Conversation With Someone You Admire



Imagine yourself at a conference, music performance, party, or other event. Across the room, you see someone you’ve always admired. What do you do? Do you skulk away? Or do you walk up to the person and start a conversation. And if so, what will you say?

Here are some conversation starters that will work with almost anyone. Use them to get some interaction going between you and the person you look up to. You’re smart enough to take it from there.

1. I really like your work.

From movie stars to CEOs to authors to researchers, this opener works with nearly anyone. It tells people you’ve been paying attention to them–and in today’s over-stimulated world, your attention is one of the greatest gifts you can give. One caveat: Do not use this opener unless it’s true. If you really haven’t been following someone’s work, don’t pretend that you have.

2. I really enjoyed your presentation.

If the person has just given a speech or performance, or if you’ve seen them onstage elsewhere, then saying that you enjoyed listening to them will win you points. Again, don’t use this approach if it isn’t true.

3. I liked what you wrote in your last blog post.

If the person you want to talk with has written a blog post or article or book that you agree with or enjoyed, saying so can be a good way to get the two of you talking. It may also work to say you disagree with something they wrote, but that can be a much riskier strategy and you’ll need to have a very sensitive touch if you try it. Saying you liked or agreed with something usually works better since few people are immune to flattery, even if they think they are.

4. I found some further information about something you’re interested in.

I was at a conference recently where Gail Sheehy gave a presentation. She talked about many of the famous people she’s written about, including Margaret Thatcher who–to my surprise–she described as quite sexy. I had to know more, so I looked up some images of Thatcher and sure enough, she had long and very shapely legs that she often showed off to her advantage. I showed Sheehy one of those images and we wound up talking off and on for the next hour or so.

5. Where did you get the idea for…?

If the person you want to talk to has done anything creative or innovative, asking where the idea for that product or work came from is likely to work well. Most people enjoy talking about their work, and there’s often a good story behind a good idea.

6. What’s your opinion about…?

These days, there’s a lot of prognostication around the coming presidential election as well as the state of the economy. Just about everyone has an opinion about what’s going to happen and most people love to be asked what their opinions or projections are. If there’s a big sports event coming up, such as the Super Bowl and you know the person is a fan, asking for their predictions is another great way to get a conversation going.

7. What’s your next project?

Most people love to talk about what they’re working on or planning, but not everyone. So this will be effective often but not always. Have a change of subject ready in case you hit the rare person who doesn’t like talking about works in progress.

8. Are you having a good event?

Asking someone if he or she is having a good time is always a good conversational gambit, even with a total stranger. Since you’re both at the event together, it subtly reinforces the bond between you as well.

9. I really love your pin/scarf/hat, etc.

If the person you want to talk to is wearing anything unusual, or unusually lovely, complimenting that piece of clothing or accessory is usually a good bet. My husband once started a conversation with Nicolas Cage by asking what kind of cigar he was smoking. Complimenting someone on their personal appearance,  such as their hair, tends to be riskier–don’t do that.

10. Join an existing conversation.

If there’s already a group of people gathered around your target with a conversation going on, don’t let that keep you away. Walk up and stand at the edge of the group, and listen for a while till you get a good sense of what they’re talking about. If you just stand nearby, chances are the group will gradually open up to include you. And if you have something of interest to contribute on the topic at hand, then wait for an opening and jump in.

11. Can I bring you a beverage?

If your target is surrounded, he or she may not be able to get to the drink or food stations. Offer to fetch something to drink, even if it’s just a glass of water. Your thoughtfulness will win you points, even if they don’t take you up on your offer.

12. Can I ask your advice?

Most people like to share their wisdom, so asking for advice is often a good way to get someone talking with you. One approach is to ask what advice they would give a young person who is just starting out and wants to succeed in their profession. (You can always invent a nephew or niece on whose behalf you’re asking the question.) Or if there’s advice you want on your own behalf, then ask for that.

13. Would you consider…?

In some situations, you only get a few moments to talk to someone high-profile and you have to make those moments count. If that’s the case, the best strategy may be to quickly ask for what you want since you might not get another chance. “Would you consider…?” is usually a good way to phrase such requests. It’s respectful and indicates that you’re not assuming they’ll say give you what you want. Besides, all you’ve actually asked them to do is think about whatever it is you want from them. That’s a lot easier to say yes to.



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