What Questions Do I Use When Meeting Someone Online vs. In Person?

Nick Slade Nick Slade • 9/25/14

The Internet provides a great venue for starting a conversation, but it lacks one thing — your physical presence. There has to be enough shmoozing in your online chats to convey personality, interest and a sense of realness. Still, it’s best to use the online setting to go down your checklist, and save the bonding opportunities for real life.

Use the web to screen and identify the kind of person you are dealing with. Ask about her job, where she went to school, where she likes to go on the weekends, if she has a regular coffee shop or bar, what her hobbies are, who she lives with, what is the last movie she saw, if she prefers blue jeans or dresses. Then ask how long since her last relationship and how long it lasted.

These questions will give you an idea about her lifestyle as well as her personality. It will give you a chance to find out if you have any hangouts, activities or friends in common — and it might even give you a good idea for a date or a place where you can meet her.

Don’t spend too long chatting online. If this one is a keeper, arrange a meeting and get more personal there. Web chat does not generate chemistry. It’s all for the head, so reserve judgment until you actually meet her. It is the open hearts and the warm bodies that will determine if this is a match.

When you’re face to face, that is the time to tell her how beautiful she looks, ask about the happy moments from her current life and childhood, find out what went wrong with her past relationships, and ask her what she’s looking for this time around. This is where you can show her the sincerity in your eyes, and comfort her by gently touching her hand. This is the time for your heart-to-hand and hand-in-hand connection to begin.