The Questions You Should Be Asking Romantic Prospects When Online Dating

Questions to Ask Online Dating

Real talk: dating — not to mention online dating — is hard enough as it is. Then throw in a global pandemic and a months-long lockdown (aka no social or sex life) and we're all confused on how to go about this foreign concept called dating. And now that it's finally becoming safe to date in person again ("vaxxed girl summer" is the new "hot girl summer"), it can be scary out there — FODA (Fear of Dating Again) is real, people.

When it comes to dating apps, it can be difficult and taxing to weed out contenders and find suitors with whom you're actually compatible. Not to mention — at least speaking from personal experience — there's nothing like a year of zero dating interaction to make you lower your standards.

So if you're as lost and confused as I was, keep reading because we spoke with dating experts Maria Sullivan, VP of Dating.com, and Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking to figure out what questions you should be asking dates — and when to know if something really is a deal-breaker.

When Should You Ask Questions When Online Dating?

When you're on a dating app, it can be hard to figure out just how much to ask (and reveal) before you actually take the leap and agree to meet up IRL. Sullivan says it's important to ask questions that give you a sense that your lifestyles are compatible — and ensure you aren't wasting your time. "In order to make the most out of your time, you should be asking questions about their everyday lives," Sullivan tells us. The point is to get to know someone's values and hobbies — but not get in too deep just yet.

Trombetti says singles should generally avoid firing off questions interview-style before or even on the first date. The goal is to keep things positive and find "a healthy balance of asking and still conversing," says Trombetti. "All things are revealed in due course."

While there may be a lot of questions you want to ask when online dating, when you place too much weight on their answers, which can prevent you from giving your date a fair shot. "It seems to be human nature to weed people out and read more into whatever they are saying and determine that you are incompatible — when this isn't really the case," she tells us.

In other words, let yourself have some fun and enjoy the process. Most of the time, you'll organically find out after the first few dates whether or not you're compatible with someone.

And if things are going well? By the fourth date is when Trombetti recommends working some more serious questions into the conversation to figure out their commitment level. If you're in a place where you're ready to commit (to the right person), you want to be sure they are like-minded, she says. As for the method of communication, like most other things, Trombetti says in person is always better, or over the phone. "Don't cut off anyone based on a text or app response — they may not be the best communicating this way and that is OK!"

The Best Questions to Ask While Online Dating

Sullivan and Trombetti helped us curate a list of helpful questions to ask online dating prospects, without coming off too aggressive or making it feel like a job interview. Some of these questions serve as great ice breakers and others can help you find out more about your date without prying too much. Bookmark this page and thank us later.

Online Dating Questions:

  • What do you do for a living?
  • What are some goals or aspirations you have in your career?
  • What has been your favorite vacation? ("Asking this question on a first date will open up a conversation about where your date has traveled and if you are both into the same types of vacation destinations," says Sullivan.
  • What’s the most interesting fact you know?
  • What is your ultimate favorite meal?
  • What is your all-time favorite movie/show?
  • Do you have any hobbies?
  • What’s your favorite holiday? ("This question may give you an insight into your date’s religion based on the answer, which can be an important part of a relationship," says Sullivan.)
  • Are you more of a morning or night person?
  • How many siblings do you have?
  • What is the level of commitment you are looking for, generally speaking?

When Should Answers Be Dealbreakers?

Now that your questions have been answered, what do you do if an answer isn't exactly ideal? Both Sullivan and Trombetti agree: differences don't necessarily make you incompatible.

"When it comes to dealbreakers, there should only be a few aside from ones that are so obvious that you would never see them again," says Trombetti. While it will depend on your own personal values, the biggie is "lack of alignment on the type of commitment you are both looking for." Religion, thoughts on children (whether either party has them already or wants to in the future), fitness and wellness, and financial or job stability, are also common dealbreakers.

"The problem is, most singles rule so many people out for no good reason," says Trombetti. "They don't have to share your love of horseback riding or your hobbies. That's what friends are for."

Sullivan agrees that differences and disagreements don't have to define the relationship, but they can turn into dealbreakers if they cause conflict that can't be resolved. "If it turns into more than just a quick fight and results in insulting one another [or] you do not come to a resolution fast and it ruins your mood for the day, then it might be a dealbreaker — and it's probably safe to say you are not as compatible as you thought."

The bottom line: Dating can be tricky, especially during a global pandemic. Ask questions along the way, but at the end of the day, it's important to give each and every date a fair chance. Follow your heart and your gut, but don't write someone off until you're sure it's a dealbreaker. Now swipe away!

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