Do you feel frustrated that you keep getting passed over in the dating pool? Do you find you’re able to get lots of dates, but none of them seem to be going anywhere? If you want to be sure you’re putting your best foot forward, take a page from the Passover Haggadah and ask these four important questions on your next first date.

1. The Wise Dater Asks – “Where do you see yourself in 5 or 10 years?”

You need to know early on that your date has the same intentions as you if you’re looking for a long-term relationship. If you don’t do this, you could end up wasting a lot of time. For example, people’s feelings about having children generally don’t change. So, if kids are a part of your vision, you need to know if your date shares your perspective. By making this question more open-ended than just, “Do you want to get married,” you allow them the opportunity to answer in their own way without feeling pressured to put a ring on your finger by the end of the night.

2. The Wicked Dater Asks – “How come your profile said you love exercising, but you just told me you haven’t been to the gym yet this year?”

Dates love it when you bust their shank bones a little bit. It hearkens back to the playground days when boys pulled the hair of the girl they liked most. Let your date know you’re not a plain matzo—that you have a little spice and flavor to you— by asking a few challenging questions. Plus, if they said something in their profile to make themselves seem more attractive that just isn’t true, you need to get the facts out in the open.

3. The Simple Dater Asks – “What’s a typical Saturday like for you?”

This question says a lot about how your date lives their everyday life. Are they a devout observer of the Sabbath? Do they like to party a little too much on Saturday night for your taste? Are they really as comfortable in a cocktail dress and heels as they are in sweats? This question is an oldie, but a goodie – and it will tell you what you need to know very quickly.

4. The Dater Who Doesn’t Know How to Ask a Question – Can’t sit and wait for their date to tell them what they want to hear!

If you’re not sure where to begin when it comes to asking questions of someone you just met online, start with their profile! Tell them what you found attractive and where you saw commonalities between the two of you. Try to avoid talking about work, past relationships, or your medical procedures and you’ll arrive at the Promised Land in no time!

Remember that a great date listens well, but also takes the time to think of clever, unique questions that will make the conversation memorable (though not creepy or weird). Asking questions that get your date to laugh, be honest, and feel relaxed around you can up your chances of getting a second date and spending next year in Jerusalem – on your honeymoon, of course!

Make sure to catch Damona every Wednesday at 11 am PST on for her weekly radio show dedicated to everything dating, mating, and relating! Read more at

  1. Can’t find where you can sign up for a free profile evaluation. Looked several times. Thank you.

  2. Dear Mrs. D.,

    I’m 73 and I’m not sure if that’s part of the problem with my profile–but I would very much appreciate it if you could help me improve what I’ve written. I know I sound very serious–and I am–but I also have a wonderful sense of humor and l ove to laugh. But I don’t think this comes across at all.

    I’m sure there is a fee attached to your service and I wo9uld be hapy to pay it.

    I look forward to hearing from you.

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