Finding a “conversation bridge” from something you said (“So, speaking of running…”) also helps you evaluate the other person in a casual way to see what type of person they are, without making him feel as though this is a job interview where you’re ticking off a checklist of requirements (Do you exercise? Check! Do you have long-term relationships? Check!)
5. Don’t grill: Getting someone to talk about himself is not the same thing as peppering him with frequent or mundane questions. There are two elements here: quantity and quality. Don’t ask more than one question per minute (inject comments and reflections in between questions to minimize the quantity of questions, making it a real conversation, not Q&A session). Also, don’t ask boring questions, even if he asked you a boring question first (Avoid: How are you? What are you doing? How was work? Was the traffic bad?).
6. Be fun: If there’s a lull in the conversation flow, try to be fun and spark some banter. Pick a neutral, third party topic, and make a comment (or ask a question) about it. For example, “Hey, did you happen to see David Letterman last night? He did the Top Ten Reasons for things overheard waiting in line to see Avatar…. Guess what #1 was?”
Asking someone to guess something is a great way to flirt and keep things interesting. And raising a third party topic (e.g., The David Letterman Show) will make you seem easy-going because you aren’t like all the other girls probing to find out if someone is Mr. Right (Avoid: What do you for work? Tell me about your parents? Do you golf?).
7. Relax him: Make the guy feel relaxed and confident by acting happy that he called and giving positive feedback on their conversation skills (even if his phone skills aren’t great—the initially shy or awkward ones usually make better partners in the long run than the instantly slick, charismatic ones!). For example, tell him, “I had a rough day at work, but your call cheered me up!” or “Oh, that’s an interesting question…”
8. Know when the party’s over: End the conversation quickly when you sense the energy level drooping. But blame it on an external factor rather than sounding bored. For example, “Oh, I just realized it’s 9:00pm and I didn’t call my grandma yet to wish her happy birthday! So sorry about that, I was really enjoying our conversation…. But good luck on that big presentation tomorrow, and I hope to talk to you soon!” This says 4 things: you’re a family-oriented person (you’re calling your grandma, awww: that’s sweet!), you’re boosting his confidence so he feels good being around you (you enjoyed the conversation, you hope to talk soon) , you’re a good listener and thoughtful person (you remembered his big presentation tomorrow), and you’re not too needy (you said “hope to talk to you soon” rather than “When will I see you? Will you call me tomorrow?).