Ask for his opinion. You could tie it to what’s currently happening in the room, current events, or whatever else you may want to discuss. Delve into “life story” topics. Ask where your conversation partner is from, how he grew up, and so on.
People you know well: ask him how he is, whether anything interesting has happened this past week, how his project or study is coming along, how his children are and whether he’s seen any good TV shows or movies lately. People you know but haven’t seen for a while: ask him what has happened in his life since you last saw him, find out if he’s still working in the same job and living in the same area, ask about his children and whether he’s had more (if relevant); perhaps ask if he’s seen a mutual friend lately.
Do you play or follow any sports? Do you like to hang out online? What do you like to read? What do you do in your spare time? What kind of music do you like? What kinds of movies do you like to watch? What are your favorite TV shows? What’s your favorite board game or card game? Do you like animals? What’s your favorite animal?
Do you have any siblings? How many? (If he has no siblings) What was it like being an only child? (If he has siblings) What are their names? How old are they? What do your siblings do? (Modify the question based on how old they are. Do they go to school/college or have a job?) Do you look alike? Do you all have similar personalities? Where did you grow up?
If you had a chance to move to any other country, which one would it be and why? Of all the cities in the world you’ve visited, which one was your favorite? Where did you go on your last vacation? How did you like it? What was the best/worst vacation or trip you’ve ever been on?
If you could only have one meal for the rest of your life, what would it be? Where do you like to go when you eat out? Do you like to cook? What’s your favorite kind of candy? What’s the worst restaurant experience you’ve ever had?
What do you do for a living? Where do you work (or study)? What was your first job ever? Who was your favorite boss in the past? When you were a kid, what did you want to be when you grew up? What do you like best about your job? If money was no object, but you still had to work, what would be your dream job?
So, how do you know the host? How did you get involved in this event? (Or, when relevant) In fundraising? In triathlons? How do you find the time to be involved in events like this?
I loved your piano performance. How long have you been playing for? You seemed really confident during your speech. How did you learn to put together such great presentations? Your run was absolutely amazing. How often do you train each week?
Avoid talking about problems in your life or other negative situations. If you’ve experienced people’s eyes glazing over when such topics are raised, it’s simply because few people expect to have to deal with heavy situations or problems in a casual, conversational context. Most people are looking for polite, interesting, and lighthearted topics to discuss and a negative insertion can really put a blight on the moment, bringing to a halt any further conversation.
Silence can become awkward, however, if you get nervous or try to cover up the silence because you’re worried about it.
Discuss others who share your interest and their achievements. For example, you might both know the marathon winner from last season and one of you might be able to expand on what this person has been up to since winning. Talk about new gear, new equipment, new insights, new tactics, etc. to do with your shared interest. Suggest new things that you could both try in your shared interest, perhaps even making a date to catch up and try something new together.
Given all you have accomplished so far, what do you think has been the most important to you/beneficial to your community? If you could be rich, famous, or influential, which would you choose and why? Is this the best time of your life? If you could only own 10 things, what would they be? If you had to choose only five foods and two drinks for the rest of your life, what would they be? Do you believe people make happiness or stumble across it? What would you do if you could wear an invisibility cloak? Do you believe in free will? What sort of animal do you think you would be if someone could change you into one? Who is your favorite superhero and why? Which five people out of all history would you choose to invite to an intimate dinner party at your house? If you won a few million in the lottery tomorrow, how would you spend it? If you could be famous for a week, what would you be known for? (Or which celebrity would you choose to be?) Do you still believe in Santa? Could you live without the internet? What’s your dream vacation?
Equally, remember the topics that seem to make people feel uncomfortable or bored and avoid these in the future.
Keep in mind funny new stories that could get you a laugh as well as remind your conversation partner of funny news stories he has read recently.
Try to not digress into tangents as you are bringing up a conversation topic or you risk losing your conversation partner’s attention!
