After playing the 100hookup game (viewing, favorite-ing, messaging, etc), exchanging a few emails and a couple quick phone calls (to make and confirm plans), you will no doubt find yourself battling nerves before a first date no matter how confident of a person you are. Once you’ve greeted each other, sat down at the bar or table, ordered drinks and discussed the menu, there is a time when the conversation may lull — and it’s nerve-wracking!

Don’t let that moment set the tone for the date. Be prepared with topics to bring up that will be a catalyst for ongoing conversation. Of course there will be the typical biographical questions (what you do for a living, your hobbies, where you grew up, your family, etc.) but most of that was likely covered in your initial emails and phone calls, and now you need to see if you can actually carry a conversation and jive with the other person.

Think of some thought-provoking questions like:

• What do you hope your life looks like in 5/10/20 years?
• Are you where you wanted to be in life 5/10/20 years ago?
• If you could have a superpower what would it be and why?
• What is your best memory from your childhood?
• Who are 5 people, alive or dead, that you would love to talk to?

The key is to not make it sound like a rehearsed question or an interview, but rather work it in somehow… “Hey that Caitlyn Jenner interview has really made me think…” or “My 96-year-old Great Uncle just passed away and I’ve been doing some soul searching…” and so on. Current events are a great tool: “Remember that Malaysia Air plane that disappeared in the ocean? It really got me wondering about the supernatural. Do you believe in…?”

Finally, listen to your date’s answer rather than being ready to pounce with your answer or another question. A lot of conversation will likely naturally occur, but if you are mentally preparing for what you’re going to say next then you will miss out. If you are a shy person then ask a friend or relative to practice with you.

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We all have dating patterns — some good and some bad. Identifying which is which is difficult. Take a look at your last bunch of first dates, and at your last few relationships. What was similar? What was different? Not just their looks, or education level, or religious level, or jobs, or even their personality… but how you felt.

For instance, when you got those butterflies in your stomach on certain dates, did those translate into serious relationships or did the excitement crash and burn after a few weeks? Many people are searching for a “feeling” on a first date, and when they don’t get that feeling they write off the person before giving them a chance. If that is your pattern, then I suggest giving some of the dates more time: if the first date was pretty good and all you’re really missing is that “feeling” then go on a second date and see if the comfort level of another meeting will help the connection.

This is an intangible feeling, but we tend to put a strong weight behind having it or not. Remember though — more couples tend to be successful when their relationship is built on commonalities rather than lust; and butterflies tend to be an indication of lust.

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In the last year, I’ve learned a lot about modesty in Orthodox Judaism. While I don’t follow it, I am finding that I like a lot of the principles behind it. About a month ago, I started covering my body more on a first dates.

Why, you ask? Dating is supposed to be fun, maybe a little bit flirty if you feel chemistry. But first dates in the long run are also about looking for a life partner. I evaluate men based on character, manners, values, and other traits that typically require having an engaging conversation.

Looking presentable and being hygienic are important in that they show effort, but they’re not everything. “Presentable” for women, especially in the summer, doesn’t have to mean “mostly naked.” I am generally more comfortable in my skin when it’s not all on display.

With this in mind, I’ve begun a new experiment. I try to look fashionable, but without showing my thighs, knees, shoulders, or any cleavage. Some guys are more receptive to this than others, but I think it’s become an easier way to dodge a bullet. If a guy seems bored or distracted by me, or he checks out scantily clad women while on a date with me, I can cut my losses and move on. I’ve been in situations before where I was keenly aware that a guy was only interested in me in a physical way. While it can be flattering, it’s not good for my self-esteem in the long-term. I like to be appreciated for my internal qualities, which can easily be overlooked on first dates.

I don’t have any data to prove it, but I think I now get more compliments related to qualities other than my looks on dates. I found them to be a rarity prior to my experiment. I’m also finding it easier to connect with people on a more personal level, and I think I’m going to stick to my new plan indefinitely.