Top Questions to Ask Your Online Date

The early part of any dating relationship is a little like a television late night talk show. You share stories, you tell jokes, and, most importantly, you ask questions. And like a late night talk show host, your goal is not necessarily to interrogate your guest and trip them up, but rather to give them the chance to show the world, and more particularly you, what a wonderful and interesting person they are.

In online dating, the questions are even more important because you often know so little about your date. You are coming into the situation cold, without knowing anything but what they choose to reveal in their online profile, assuming that information is even true. Also, without being able to look in someone’s eyes and observe body language, it can be a challenge to feel that you truly know someone, and asking the right questions can help with that.

By the way, for legal reasons, our first question in online dating should be “Are you at least 18 years old?” Nothing kills your amorous feelings more than getting caught in a sting for pedophiles, although you’ll likely have many opportunities to date in prison.

Appearance Questions

If your date doesn’t have a profile picture posted and won’t share one privately, it’s a definite red flag. Still, if you want to proceed with them anyway, you’ll need to play “twenty questions” about their appearance. “How tall are you, what do you weigh, what color is your hair,” etc., are all acceptable questions for an online date if they have refused to share a photo. Whether or not you choose to believe the answers is up to you.

Questions about Goals

If you’re looking for a true, legitimate dating relationship, goals are very important. If you’re going to be with somebody a long time, and perhaps even marry them and have kids with them, you want to know what they want out of life. Even if they just want to drift along and go where the wind takes them for the rest of their life and that’s fine with you, you’ll still want to know it up front.

It’s also fair for you to wonder what your date’s relationship goals are. If you’re looking for a quick fling without your wife finding out and she’s looking for someone to father her next nine kids, there is a fundamental disconnect there that you’ll want to find out about early.

Questions about Family

Maybe if you’re just looking online to find a booty call, you don’t really care that the person you’re interested in was adopted and considers themselves to be a sister to 200 other kids from a Ukrainian orphanage. You might start to care, however, if she has an older brother who is an MMA fighter and likes to practice his new moves on anyone he perceives to be disrespecting his sister.

If you are looking for a long-term relationship, family becomes more important. For men, it’s a popular idea, with some truth to it, that how they treat their mother is how they’ll treat their wife or long-term girlfriend, so women would be advised to ask about that relationship. Also, if children send you into uncontrollable fits of anxiety, you might want to know up front if your date has triplets and another on the way.

Questions about Other Relationships

Have you ever made it to the second or third date before you learn that the person you’re dating is married or in a committed relationship? Then you’re not asking the right questions! Whether you care or not, you need to know if your date is married because it changes the whole dynamic and expectation of the relationship. It also gives you a clue on whether or not you need to worry about jealous spouses.

Ex-spouses, girlfriends, and boyfriends are also good to ask about, for a variety of reasons. If every ex-girlfriend is a whore or every ex-boyfriend is a jerk, guess what you’re going to be when this is over? On the other hand, if the relationship with the ex is so good that they’re still living together as friends with benefits, well, that’s a whole new set of problems.

If your date has recently gone through a bad breakup, this could mean that you’re a rebound date. If you’re looking for a quick lay, that’s no problem, but if you’re looking for something long-term, it might be an issue. Another problem with bad breakups is that they often lead to angry ex-partners looking to smash up your car, or your face, in the parking lot of wherever you go on a date. Forewarned is forearmed.

Questions about Sex

If you’re on a Christian dating site, you might want to avoid the sex questions until you’re on the 57th date and already engaged. If, however, you are on a hookup site, sex will be a primary concern and you may as well ask about it right up front. If your entire goal is to find someone who can cut their initials into your back with a whip, you don’t want to wait until you’re in the bedroom to find out that slow, soft, and gentle is the only way your date will roll.

Besides a general question about what someone is into, if they seem comfortable with sex talk you can get away with more specifics. Ask about their best experiences, their fantasies, and what their own best sexual talents are. If nothing else, it gives you something to look forward to.

Dating always seems to feature a question-and-answer period and, in online dating, these questions and answers are even more important. The nature of online dating makes a slightly wider variety of questions acceptable, so you should feel free to ask about what’s important to you—everything from family to sex. The answers should tell you whether it’s worth meeting this person or if it’s time to move on to the next profile.