Trent from Washington DC asks…

What are some good conversation questions to ask a pretty girl on a first date? I feel like an idiot if there’s a break in silence and I don’t know what to say. I normally end up looking down at the table or the food in front of my face.

Hey Trent!

Well, you said quite a mouthful right there! I find that guys tend to have the hardest time just talking to a girl that they’re really into, let alone keep a conversation flowing and engaging.

Here are some pointers to get you started that will really make a difference on your dates:

1.  Don’t get all goo-goo-eyed over her “hotness!”

What I’ve found working with men is that the hotter the girl is, the more nervous and tongue-tied the guy gets and you end up killing your own game! I know it’s hard, but try to forget about how hot she looks on your date and keep the focus on where it should be – on discovering who she is, what she’s all about and whether you even LIKE her or not. That keeps your head in the right place, and keeps the power properly balanced (rather than drooling over her like she’s a god).

2.  Don’t think about “what to say,” but instead think about what is it that you want to find out about her?

What kinds of questions would give you insight into who she is and whether or not she has the top qualities and lifestyle that you’re looking for in your “ideal woman?” Pretend that you are on a scavenger hunt to find those things out, and by way of that you’ll actually be genuinely curious and have plenty of interesting things to talk about.

3. Have some ready-to-go questions and conversation topics that you can pull out that are woman-friendly.

Ideally you want to ask questions that are open-ended (not those that just require a “yes or no” response) and that can generate stimulating or fun discussions. I always find that hypothetical situation-based questions work well with girls because it forces us to use our imagination and the process creates great opportunities for flirting and bonding.

Try questions like “If you could go on a 24-Hour Fantasy Date, to anywhere in the world and an unlimited budget, where would you go and what would you do?” or, “What is the craziest or most adventurous thing you’d want to try?” Women love questions like this, so try some out and get ready for fun discussions.

4. Women love to be asked what our “favorite things” are, and the reasons why.

They not only give us an opportunity to share and talk about ourselves (which we love doing), but also give you easy access to connect on any of those things that you discover that you have in common with us. Ask her things like, “What are your favorite parts of your job?”, “Where’s your favorite place that you’ve traveled to?”, “What’s your favorite animal?”, or “What’s your favorite thing to do on a Friday night out?” Those questions always get a girl’s endorphin levels rising because she’s talking about things she loves – and connecting that happy feeling to you!

5. And if you ever do fall silent, just roll with it!

Sometimes silence can be golden, and you can just take a moment to relax and think about what else you want to know about her. Once in a while, let her be the one to pick back up the conversation. You don’t always need to fill in the silence or keep babbling on nervously just because you’re afraid to let it drop.

That actually creates more awkwardness than if you’re just confident with the pause.  We don’t expect you to be a Comedian or One-man Entertainer putting on a show, just a guy who is interesting and who is interested in getting to know US!

So when you can get out of your head and keep the focus on staying curious about HER, it not only keeps the conversations flowing but it has the other side effect of her feeling like you’re genuinely interested in getting to know her – not just trying to get in her pants because she’s hot… Which will in turn have her be attracted to YOU because that’s rare for men to do!