SurvivingInfidelity.com^®

When you’re meeting someone for the first time, whether randomly in public or online on OLD, what are some questions you like to be asked about yourself? What’s the most interesting question a person can ask you? And how can a lady make it non-awkward for you both?

Sorry, one more question: do you think a lady is still worth talking to if she’s shy but still making an effort to engage?

Hi Silverhopes. I think that OLD has its pluses and minuses. One of the pluses is that you can overcome your shyness with a person by texting until you’re comfortable meeting that person face-to-face. As an introvert myself, I don’t disregard a woman solely because she’s shy, as long as I perceive it to be shyness as opposed to a lack of interest.

I don’t mean to be playing semantics but I think that instead of looking for the “most interesting question”, you should be looking for questions/topics that a man would enthusiastically answer, such as what are you most proud of? What activities do you do for fun? Tell me about your kids (if he has them)?Tell me about your best friends growing up? Tell me about your first car, favorite car, fastest car, etc? To me, “interesting” connotes thoughtfulness which might be better saved for a second date. I expect to be asked the “why are you divorced” question by the second date or third date.

[This message edited by Alonelyagain at 7:37 AM, February 18th (Thursday)]

Great topic! I've had my share of awkward first conversations. It doesn't really matter what the questions are as long as the conversation is two way and engaging for both. I like any questions that allow my sense of humor to come out (I have a million bad punny dad comebacks) and that encourage me to be able to ask a question back. I also make jokes about awkward pauses and blank stares.

I don't want to be asked right away about my late marriage. But, if I'm asked about my sons, I'll talk a lot.

Also, despite what many of us say, we do like to talk about ourselves so questions that help us reveal more about who we are are good. Hobbies, activities. Then we can find common ground. If the questions are about activities, we feel comfortable talking about them more than about ME specifically.

I always started with the basics. I am an adventure seeker/adrenaline junky and I love roller coasters and horror movies and it's how I spend my free time. For me, I needed a man up for adventure like I am. So by finding out what they like to do for fun, it weeded out those that were not looking for the same fun as me.

Questions to ask...

What is his taste in music?

What are his hobbies?

If he has kids, ask about them.

Where has he traveled and where would he like to visit?

Does he read?

What is his career and does he plans for major changes?