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3 Ways to Change Your First-Date Experience

3 Ways to Change Your First-Date Experience

Simple changes that can make a big difference.


What I hear most from self-proclaimed “older singles” is that they feel frustrated. Every first date is another big effort from which they never see results. It’s that feeling of ‘Here we go again, another boringly repetitive date.’ Luckily, there are a few ways to break out of old habits and change your experience (and these tips work just as well for the first first date as for the 40th first date).

1. Change the way you ask questions.

Your goal on a first date is to see if you enjoy spending time together and can start making a connection. That’s it! If this is the latest in a long line of dates, making a connection might feel incredibly difficult. But open-ended question can help making a connection much easier, if there’s a connection to be made. Closed-ended questions, on the other hand, are conversation stoppers.

Here are a few examples of easy rephrasing that can lead to greater success a first date:

Don’t ask: “Where did you move from?”
Try asking: “Why did you decide to move?”

Don’t ask: “Do you have any free time?”
Try asking: “How do you like to spend your free time?”

Don’t ask: “When did you start your job?”
Try asking: “In what ways is this job different from your last job?”

You’ll notice that these questions are nearly the same. The difference is that the first options can be answered in one word, which might be followed by an awkward silence. Awkward silences can be avoided. The second option gives your date the opportunity to tell a little story, to share a small piece of his thoughts or feelings.

You can also answer questions this way even if your date asked a closed-ended question. If your date asks, “When did you start your job?” help him out. Answer the question and then tell him how much you like your job, what it was like compared to the last place you worked.

2. Change the question you ask yourself.

“Is this my soul mate?” That’s the million dollar question. It’s such a consuming question that you might be asking it over and over again while you’re still on the date. And we all want to know the answer asap. If you’ve been dating for a while, you probably think you’ve gotten good at figuring out what works for you and what doesn’t. What’s more, you’re probably right! Making a snap judgment may have become second nature to you. You want to be efficient in your dating for marriage process; you don’t have time to waste.

Yes, be efficient. However, really being efficient means that you are dedicating a minimum of one full date to investigating whether or not this person is your soul mate. There’s nothing wrong with asking “Is this my soul mate?” -- but not until after the date. That means on the date, the only question I want you to repeat over and over again is, “Am I present in the moment?”

Ask yourself if you are really hearing and seeing who is in front of you (even if you don’t want to marry him or her!). Ask yourself if you are being yourself. Make sure you stay in the moment of the date and out of your head. When you return home from the date you can ask yourself if this was the one. Even if you already know the answer is “no,” practicing this marriage-minded approach to dating will help you on your next first date.

3. Change the way you describe yourself.

“So, tell me a little bit about yourself.” People often ask this on a first date when they don’t have a more specific question. Trying to answer such a blanket question often leaves people speechless. Oy! Where do you even begin?

You begin with the end in mind. What is your goal? Your goal is to identify whether or not this is your soul mate. So share how are you unique, what makes you you. What are you going to say that will quickly and clearly differentiate you from others and express who you are? It’s a good idea to give this some thought before your next date. By first understanding yourself and your unique qualities and combinations you will be better able to articulate who you are to another.

Remember, don’t try to be what he or she is looking for. You simply want express clearly who you are. You may be surprised at how much someone will love exactly that person.

Changing your first date experience isn’t easy. Putting your best self forward can be especially challenging after years of dating. But these simple changes can make a big difference. Pick one thing you want to change on your next first date. And let me know how it goes. You may or may not find your soul mate on the next date, but you will find more of yourself which will ultimately lead to your soul mate. May your journey from here on be short, sweet and filled with support from the network of people who love you!

July 6, 2013

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Visitor Comments: 31

(29) Marc, January 19, 2014 4:40 PM



Very well said. Most people who are "fried" from dating truly feel it is an errand and are not "In the Moment" as you say. Knowing it is just not another "task" on your to do list that day is paramount. Enjoy the experience and process. Hope people heed your advice!

(28) SusanE, August 5, 2013 8:45 PM

Friends Friends Friends

Why would you go out with someone alone on a first date? Call him and go out with some of your friends on a double or triple date. Much easier on the conversation, and you will know how he interacts. if there is a second date you will have something to talk about. Then suggest double dating with some of his friends. If he doesn't want to or doesn't have any friends it's time to move on.

(27) Robert, July 24, 2013 6:15 AM

Dating is like a job interview, but it shouldn't feel like one.

Hi Aleeza,

The problem with most "first dates" is in how to avoid the date sounding like: (A) a "job interview," (B) a "psychological examination," or (C) a "sales promotion" by a "used car salesperson."

Dating is all about "selling oneself." And the "deal is closed" with a gold ring and signatures on the marriage contract (ketubah) by the party of the first part, the party of the second part, and at least two witnesses.

I know a lot about "asking leading questions," and avoiding "yes or no questions." In my experience, most people don't want to be "sold." They initially just want to know "who you are" on the surface and can they trust you. And if the other person is truly interested, they'll want to know more about you.

The problem that I and others find most often on our dates, especially us older singles whose time is precious and feel quite jaded about their dating experiences, is that when you start to ask "personal questions," the other person can either "open up" or "clam up." If the other person "opens up," then you're very lucky and you will both share a very easy going conversation with just the right amount of verbal exchange.

If the other person "clams up," it's because he or she doesn't trust you enough, isn't comfortable sharing personal information in general, or doesn't want to be hounded with typical "first date" questions like "So what do you do?" If such is the case, then the sales deal was closed before it started. Save your time and move onto the next potential prospect.

We should all learn the dating "buying signs" from our dates. And if one doesn't know them, LEARN THEM!!!

I hope people learn from this article and that it helps us singles to meet our "bashert" and have excellent dates that help us to meet that "right person" for us and get us all married soon.

I wish you much continued success in your career.

(26) Anonymous Female, July 12, 2013 10:24 PM

listen to this woman!

Aleeza knows of what she speaks. She can help...if we let her... :-)

(25) Anonymous Girl, July 11, 2013 9:22 PM

Great Article. Helped me!

This article is very well written and I appreciate all of the advice Aleeza gives. Having met with her in person and hearing her approach to dating, I know that my first dates post-working with Aleeza were so much better than before. I hated how first dates would sound like interviews or a sales pitch, but having changed the way I phrased questions, and really just letting go and having fun, have made my first dates so much more pleasant.

It's so important to be yourself, and I appreciate that Aleeza touches on this subject. I find that too many individuals are trying so hard to be someone they're not in order to find their bashert, and it's just sad really. Be who you are, and be in the moment.

Keep up the good work Aleeza.

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