Dating Expectations

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What is the goal of each date?

There are no exact rules when it comes to dating, contrary to some modern-day books and articles. But since misguided dating expectations can kill a date, it’s helpful to know your goal for each date.

Date #1: The aim here is to enjoy each other’s company, to get to know a little about each other and to start warming up to being around this person. Some people are better than others at being open and friendly on a first date. I consider a first date a success if you are either feeling positive or neutral about the person you went out with. If you are feeling negative about the person then I know you’re likely to say no to a second date. Neutral doesn't feel great, but it might still be worth giving it a shot. Some happy couples started out feeling neutral on their first date. If you’re feeling positive about the date, it could be a real feeling or only one of infatuation. Only time will help you to tell the difference.

Date #2: It’s good to keep expectations low for this date. A great first date can lead to a second date that bombs. A neutral first date can lead to another neutral date. Of course, a second date could also be amazing, in which case you won’t need help moving to a third date. However, don’t let a neutral second date throw you off course. Take a minute of quiet reflection after this date and answer these two questions: Do I want to know more about this person? Was s/he pleasant to be around? I’m less concerned with the actual date and more interested in your reflections about the person with whom you just spent a few hours. If you’re feeling neutral, I’d say try again. If you’re confident this isn’t for you then it’s time to end it. The goal of this date is, in a small way, to begin desiring to know this person better or to be around them more.

Dates #3-5: For the next few dates, it’s good to have a combination of fun mixed with getting to know your date. All fun and nothing personal won’t help you build a lasting connection. Too much serious talk will deflate a good thing if it’s not integrated with activity and enjoyment. We long to spend our lives with people we enjoy being around and it’s good to look for someone whom you can connect to and share things in common. Start to make the conversations on your dates more personal, but don’t divulge your deepest secrets just yet.

Dates #6-10: Sticking with someone for the next few dates should start to be an enjoyable process (unless you struggle with anxiety, depression or other challenges in which case it may take you longer to enjoy the process). Deeper conversations should start emerging naturally as the dates progress. Things like your future hopes, wishes and dreams, as well as slowly revealing personal challenges you’ve overcome, are subjects that should come up. People tend to speak about themselves negatively and justify it by saying, “I just want to be honest. I don’t want to hide anything.” Generally speaking, people can see the faults of others; we don’t need to draw extra attention to faults that are already visible to the naked eye. If there are any more serious things you need to discuss, such as illnesses, you will need to determine when to have that conversation. Some people start to share things early on while others wait until the relationship is further along. Since each couple dates for a different amount of time before reaching chuppah, the time frame will be different for each couple. I suggest you speak to your mentor to guide you in how to best approach discussing sensitive subjects in dating.

Dates #11+: These dates are confirmation. I like you and you like me. The more time we spend together, the more time I want to spend together. I have come to recognize the good side of you and I like it. I am also able to identify at last five faults about you and accept those as a part of you. In layman's terms: I accept both your good side and “other” side.

Your personal mentor will be able to guide you through different dating situations. If you don’t yet have someone you trust, take time before your next date to connect with someone in your community who can support you. Also remember that what worked with one dating situation won’t necessarily work for another. Each relationship is unique.

May you have insight into your dates and may you find the right one with ease.

Want to speak in person about your dating life? Come to the Aish Conference this year! I’ll be giving a class and will be available to answer any dating questions you may have. I’d love to meet you!

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