Good Random Questions to Ask a Guy to Keep the Conversation Going

Keep in mind the topics he likes so you can ask questions that spark conversation.
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Keeping a conversation going with a guy can be tricky, especially if you are too tongue-tied to find the words. Avoid firing off a round of close-ended questions that make it feel like an interview and not a fun conversation. Instead, rely on questions and topics that show your interest in learning more about him.

1 Current Events

Whether you’re discussing events from the news or bringing up a new movie you haven’t seen, current topics can be great avenues into other areas. For example, asking what he thinks about a new movie could lead to a discussion of favorite movies. These types of getting-to-know you questions can help reveal hidden passions and develop into a great conversation. Discussing current events can also move the conversation along because you’ll be able to participate instead of just asking questions.

2 Flirty Topics

If this conversation is a chance to show your romantic interest, try some flirtatious questions. Ask if he’s been working out or just got a haircut. This lets him know that you pay attention to his appearance. It also gives you the chance to compliment him while keeping the conversation going. For example, if you are flirtatiously asking him about his new shoes, toss in a few related questions about the types of activities he does in those shoes.

3 Insightful Questions

If you want to fill the silence with a rousing conversation, ask questions that make him think. For example, “If you had to move to another place for a year, where would you go?” or “What is your favorite day of the week?” It is important to listen to how he responds, chiming in once he’s done. If he responds that his favorite day is Thursday, ask him about his favorite Thursday in recent months. Listening to his responses can also help you shine as a conversationalist, according to social worker Maud Purcell in the article "Making Conversation: A Skill, Not an Art" on the PsychCentral website.

4 Ice Breakers

Asking good ice-breaking questions can show the guy that you have a variety of marvelous attributes, such as attractiveness, confidence and strength, writes Jeremy Nicholson, psychologist, in the Psychology Today article, “Break the Ice: How to Talk to Girls and Guys." Ask questions that are lighthearted and random: “What superhero do you think is the most overrated?” “Would you rather have a personal trainer or a personal chef?” “What Olympic sport would you like to try?” or “Name a popular food that you’ve never tried.” These are all great ways to bounce around topics and find new things to talk about in the process.

Based in Chicago, Nicole Nalls has been writing and editing career and education-related articles since 2008. Her articles have appeared in "Venus Zine" magazine, as well as a number of online publications. She holds a Bachelor of Science in sociology from Illinois State University.