How to ‘Dig Deeper’ to Connect with Your Match

If you participate in eHarmony’s guided communication process, at some point, you’ll be prompted to ask and answer three open-ended questions known as “Dig Deeper.” As the name suggests, they’re intended to give you and your matches a chance to explore a topic near and dear to your hearts more thoroughly.

Yet there’s an art to picking the right questions out of that long list suggested by eHarmony. (You also have the option of writing your own.) You want to find the sweet spot of inspiring your matches to do some revelatory soul-searching and not complain, “Oh no! I just got back from work, and now I have to answer essay questions!”

With a little strategy, you can choose questions that help you bond with your matches and get you closer to a first date. For example, if your match included a long list of recent exotic travel destinations, he might appreciate the chance to brag about them a bit if asked: “What’s the most adventurous thing you’ve done in the past year?” That’s a win. On the other hand, if your match is a child of divorce, you risk making her feel unnecessarily defensive by bringing up the sensitive subject “Describe your parents’ relationship with each other.” Until you know more about your matches’ family backgrounds, that might be a good one to skip altogether.

Here are some tips to help you be a better inquisitor:

1) Use clues from their profiles

People write their profiles trying to describe what makes them tick. (Yes, some people are better at it than others.) So pick your questions according to what you think they want you to think they’re about. If your match includes lots of photos of her competing in triathlons, sailing, diving, skiing, cycling, and hiking, it’s a good bet she’s looking for a partner to participate in her active lifestyle. In this case, you can’t go wrong by asking, “Describe an interest you have that you would truly hope your partner could share with you.”

What if your match writes that he’s proud of being an involved single dad to three school-age children? He might not feel you get him if you ask: “In general, how many nights a week do you go out for entertainment?”

In the same way, if she mentions in her profile that she’s newly divorced, you can guess that she’s trying to come to grips with a new family identity that doesn’t include her ex-husband’s relatives. She probably won’t appreciate being asked: “How big is your extended family? What are the holidays like for you and your family?”

2) Give them opportunity to brag

There are certain questions that everyone likes to answer because they give us a chance to highlight what we do well. For example, most people think they’re good at relationships, so they might like the chance to answer: “What do you think are the three best traits you have to offer a partner?”

You’ll also help your matches sell themselves if you ask: “Looking back on your life, of what are you most proud?”

3) Ditch the agenda

You have the opportunity to ask questions that are important to you, but you have to consider how they might be perceived. Some topics may be better explored after several dates. For example, if your ex was terrible with money and ran up his credit cards, you might want to be extra sure your next partner is financially responsible. Yet you risk seeming overly preoccupied with the subject if you ask: “What are your general feelings about money and personal wealth?”

Similarly, the topic of gender roles is an extremely complicated one and deserves a long conversation to sort out the nuances. Do you really want to give your date the wrong idea about your views by posing this? “How important is it to you that your partner fulfill traditional gender roles? Would you like a woman who will cook, shop, and keep house? Would you like a man who maintains the cars, manages the finances, and is handy around the house?”

4) Stay positive

We all long for a sweetheart who will love us just as we are. So you probably won’t impress your matches if you focus on how they could change themselves already by asking: “If you could change one thing about yourself, what would it be?” And well, you probably won’t feel closer to someone who asks about your past failures. So feel free to pass on: “Looking back at your life, describe one particular event that you wish you had handled differently.”

5) Make it easy

Finally, you have a lot better chance of moving along the communications process if your matches don’t think of your questions as “work.” So avoid those that require a lot of soul-searching until you get to know each other better. After a busy week, your match might not be in the mood to answer: “Describe your emotional health.”

You don’t want to turn off your matches before you even get a chance to go on a date. So pick questions that allow them to feel good about themselves and inspire them to want to meet you. An added bonus: You’ll have a list of positive topics to talk about.

Which questions do you love or hate?

About the Author:

Sarah Elizabeth Richards is a journalist and the author of Motherhood, Rescheduled: The New Frontier of Egg Freezing and the Women Who Tried It. Her writing has appeared in The New York Times, The Wall Street Journal, Marie Claire, Elle, Cosmopolitan, Slate and Salon.

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