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Top Five Questions to Ask Your Online Date

by Marni Battista - May 6, 2013

If you just started online dating, or perhaps you’re a veteran, there are a few important questions to ask your potential date so you can more easily determine if he or she is a suitable match for you.

Below find a list of Dating with Dignity’s top five questions you should ask an online date.

Things to note: Please DON’T send a list of questions in a personal email. You’ll make your potential suitor think they’re interviewing for a job! Sprinkle them over a few notes back and forth, and try to make them flow organically. Writing an email that starts with “Hi. What’s your most embarrassing moment?” is probably not going to get the kind of answer you’re actually looking for. Better yet, try to take it offline as quickly as possible so you can move away from being penpals and move into live “data-dating,” in which you’re collecting data about your potential partner while having FUN.

We do believe that while the best way to get to know if you share values as well as chemistry is to observe whether a person’s actions match their words in real life; however, as a precursor, use this list to discover if that “future special someone” you just met online is the real thing.

1. What are you looking for in a relationship? Possible answers to this question include “I’m just looking to have fun, and if I meet the right woman then I would be open to a relationship,”  “I’m looking for ‘the one,’” or “I’m open to the possibilities of a long-term relationship, but I’m sort of looking for something casual right now.”

Most people online are fairly honest in their intention. Based on their answer, you can evaluate if what they’re looking for matches what YOU are looking for. If it does, great! And if it doesn’t, someone else is right around the corner.

Remember, once he meets you, he will most likely not change his relationship goals; thus, beware of the “kick the tires” type of dater who says “If the right one shows up, then I would be in a relationship.” The truth is, this person is more likely to be a casual kind of person rather than a partner who is really ready to commit.

2. What’s your most embarrassing moment? This one will help you determine if your online date has a sense of humor! Opening up with your story is a great way to grease the wheels so that they feel comfortable opening up to you! Remember, though, to pick a story that reflects a cute or quirky habit you may have. Sharing (a la “Ready for Love”) about a bodily function oops is never sexy. Keep it light, flirty and fun. It’s an opportunity to laugh together, show your confidence, and nothing more.

3. What does your ideal Saturday morning look like? Having similar schedules or ideas for how to spend a weekend is a good indicator of your compatibility with an online date. If their idea is a six a.m. bike ride followed by a full day of work, and you prefer to lay in bed all day and catch up on ‘Game of Thrones’… let’s just say it might be slightly more difficult for you two to find common interests: not impossible, just less likely!

4. What about my profile made you want to write me? This can help weed out someone who mass copy/pasted a message to 50 other people…and will make him/her actually read your profile! Also they’ll have to tell you if it was your photos, your wit, or some combination of both. It’s a great question also to see if your suitor is comfortable giving and receiving compliments! Watch out for self-deprecating humor. If she or he has a hard time with that, it could be an indication that the person may not truly be ready to let someone in. Being able to give AND receive are key indicators of real relationship readiness.

5. Where does your family live? Do you see them often? Family values are pretty important to most people. And if they aren’t? While that’s acceptable, you want to be sure that the other person’s perspective on family matches yours. Do they never see their relatives? Do they talk to their mom on the phone daily? These interactions will DEFINITELY affect your potential future together, so it’s a great thing to know about ahead of time!

DON’T ask how much money they make. Don’t ask things like, “When did your last relationship end and why?” Think of your email as a coffee shop date: would you ask those types of questions on a first date? We hope not.

Do you have any favorite first date questions?

Learn more about relationship coach  Marni Battista and Dating with Dignity.