There are few situations more awkward and stressful than a first date. You’re basically on a joint interview to be one another’s future sexual and romantic partner, yet you’re also supposed to be cool, calm, collected, and act like you didn’t just spend two hours picking out your outfit and waxing your entire body “just in case.”
So many first date stumbles happen because of bad communication or lulls in the conversation. It’s not easy to get to know someone without feeling like you’re stuck in the lightning round of a trivia game where the main subject is you and your entire life’s history. That’s why I sought the advice of a professional to help you up your game. April Masini is a relationship and etiquette expert and author based in New York City. She also dispenses vital relationship advice on her popular forum, Ask April, and has a bevy of foolproof tips to help you get more out of your first date conversations.
Whether you’re looking for long-term love or just want a fighting chance to make it to date #2, here are six things you should be asking every time you meet up with someone new.
1. “How long have you been single?”
Hopefully the person you’re on a first date with has all their loose ends tied up and is more than ready to mingle. Unfortunately, that isn’t always the case. “Believe it or not, lots of people think they’re single—and they’re only single in their minds,” warns Masini. “Use the first date to share and learn about your marital status, previous relationships, and children. These are very important pieces of information, and if you’re not online dating, you may not know this info about each other until you meet up.”
2. “Do you like what you do for a living?”
You want to figure out what type of lifestyle your date has, but you also want to figure out what they want in the future, Masini notes. Giving them a chance to talk about work helps you suss out information about their finances, ambitions, and what makes them tick, without you having to break out your CIA-level interrogation skills and completely kill the mood.
3. “What’s the best thing about living on your own?”
It seems like such a simple question, but it can actually reveal a ton of vital info. “This question gives you insight into your date’s feelings about moving out from his or her parents’ home (or if they even have), and how they get along with roommates or how they came to live alone,” says Masini. “You’ll learn a lot about them and get into a spirited conversation, which always makes the first date great.”
4. “How’d you feel about college?”
Education is a big deal to us millennials, specifically when it comes to our debts. A 2015 survey by the National Foundation for Credit Counseling found that 57 percent of respondents had reservations about dating someone with large amounts of debt, and 37 percent said they’d put off marriage until the debts were repaid. “You may be dating someone who didn’t go to college, or has hundreds of thousands in student loans, or who has just applied to go back to school for an advanced degree, or wants to,” says Masini. Asking about school helps you learn about “their goals, their finances, and their feelings about education and the work marketplace.” It also gives you a chance to talk about yours.
5. “What are your deal breakers?”
We all have those little things that completely turn us off. For instance, says Masini, maybe one of you has staunch political views, or you’d never want to be with someone who works in a particular industry. Those are things you both need to come clean about. “Know what your deal breakers are and find out if they exist with your date as close to that first meeting as possible,” says Masini. “And if you don’t know your deal breakers, call up your best friend and ask that person to help you figure them out.”
6. “I’m having such a great time!”
Okay, so this last one isn’t exactly a question. But, if you’re really feeling the chemisty and you’re tempted to ask something like, “So, what are you looking for in a relationship?” this should be your go-to instead. “Organic is much sexier,” says Masini. “You can find out what someone is looking for in a relationship without grilling them like a human resources department vetting for a job position… This kind of conversational vector will get you a lot more information about your date than asking a question, and it allows you to ask follow-up questions that are a lot less conspicuous than sipping a first glass of wine and launching into your oral questionnaire! ”