The Modern Answers to All Your First Date Questions

So, who picks up the bill?


(Last Updated on April 27, 2019 by Datezie Editors)

If you ask most singles currently in search for a mate, they’ll agree… dating sucks. Or maybe they won’t be that negative if they skew more of a ‘hopeful’ romantic than a hopeless one, but they will say it’s complicated. In recent decades, technological shifts have sent most of matching online via popular dating sites and apps. The fight for equality within the workplace has also extended itself to intimate relationships, making gender roles less divided and more balanced. Ease of communication through various mediums has actually, in some instances, made knowing where to reach out more problematic—text, call, email, Instagram message?

But while many aspects of finding a partner have transformed, the worries surrounding partnerships have stayed the same—or heightened. In fact, many people still have the same questions swirling in their head following a first date, but there are more modern versions of the answers: “Online dating and apps introduced a new way of meeting potential partners and dating. Sometimes keeping up with ‘the unofficial rules’ is impossible when they constantly change or couples lack dating experience,” explains dating expert Chris Vitale. “First dates tend to make or break any chance of kindling of a relationship, and this causes a great deal of anxiety and stress for both men and women.”

Instead of Googling, scratching your head or texting your WhatsApp group of friends, allow these dating and relationship experts to lay down the new law for you:

Q: How long should you wait to follow-up after a first date?

A: One to two days.

When you look back on the great loves of your life,  your first date was usually one for the books. The makings of the start of an amazing love story. All of the feels. A great first date is often a double-edged sword, since it leaves you wanting more—and not being sure of how to articulate it. The hard truth according to sex and relationship therapist Courtney Geter is there is no golden rule on how long to wait to follow-up. How come? Well, it’s subjective—and while you might feel great anxiety wondering about the right time to thank them or ask for another meet-up, your potential other half could be much more relaxed about the process. Regardless though, Geter says to throw out that standard three-day rule. “Although distance may bring more closeness, don’t wait too long to follow up even if you don’t feel there is a rush. If you are truly interested in this person, I advise calling or texting no more than 1-2 days after the day,” she recommends.

So if you had an amazing time with your date and you want to say it right-then-and-there once they drop you off, or your Uber gets you home? Do it. Don’t go overboard—but feel free to show your gratitude.

Q: Who pays for the first date?

A: Still the man—or whoever initiated.

Even in modern dating, executive editor and founder of, Lori Bizzoco says most of the time, men end up paying for the first date, and it remains an acceptable and an often-expected practice. Many women—even those who own their own companies and own their home homes—appreciate the gesture at the start of a could-be relationship.

However, other ladies are more comfortable paying their own way to set the stage for equality within a partnership. If this is the case, sex expert and educator Hunter Riley urges women to let their preferences be known, to avoid any mishaps. “Going back to antiquated dating rules, it’s unfair to everyone involved if only one partner pays for the date because of their gender. It can also plant some level of expectation into the partner that paid about what should happen on the day,” she continues. “That’s why I appreciate the rule of ‘if you ask someone out, it’s fair that you will be taking them out.’

Q: Who initiates the first date?

A: Whoever wants to.

Many relationship and dating experts agree that thanks to online dating, it’s fair game in terms of initiation for the first date. It’s often accepted that men or women will be the first to suggest an in-person meet-up, or at least take the conversation from dating apps to texting. However, if you’re the type of person who wants a man to ask you out instead of being tasked with making the move yourself, Geter recommends letting him know you’re intrigued. This will make it less intimidating for him to put himself out there. “This allows him to suggest a concrete date,” she adds. And on the other hand, if a man is hesitant about asking a woman out, again, Geter says let her know you are very interested in her and meeting in person. If she reciprocates, then suggest a specific time and place.

Q: Should you kiss on the first date?

A: Sure!

And hopefully, you’ll be dying to by the end of the date. Since most people attend first dates–and sign up for apps—with the hopes of meeting a special someone, a kiss shouldn’t be a doubt, but rather, an expectation. As couples therapist Dr. Sarah Schewitz shares, If the mood strikes you, absolutely pucker up!. “I am a big advocate of doing what feels good for you in that moment. Even if you never see him or her again, would you have any regrets about kissing?” she adds.

Q: Should you have sex?

A: It’s up to you.

As the ‘ole saying goes: why would you buy the cow when you can get the milk for free? Sexist and dated, many experts in the past have strongly recommended against hooking up on the first date if you’re in the market for a relationship. However, it’s becoming more and more accepted, according to Vitale. This could be because younger daters are more comfortable with allowing a relationship to evolve, as opposed to following pre-set guidelines. “Rules are meant to be broken with modern dating, and a small percentage of first dates end with getting hot in the sheets,” he shares. Though there is nothing wrong with bringing someone home on date one, when you don’t know a person very well, it can be difficult to build intimacy. “Keep in mind that sex during a first date often results in awkwardness and, even, regret later on. For those seeking a serious, long-lasting relationship, stick to informative questions and light-hearted conversations—outside of the bedroom,” Vitale adds.

If you do feel ready to go all the way after a few drinks or a meal, Riley says to have a gut check with your date first, just to ensure you’re both on the same page. “There’s nothing wrong with having sex on the first date, as long as everyone is on-board and consenting to it. If you are having sex on the first date, it’s a good idea to have a check-in conversation with them (while you’re both fully clothed) to talk about boundaries, safer sex protocols, when you were last tested, what you like in bed, and also what you don’t like,” she suggests.

Q: Where should you go for a first date?

A: Somewhere you can focus.

In the modern age, Geter says it’s important to follow the same principles from past decades, but with a twist. In other words: choose a bar, a coffee shop or another place where you both like—and minimize distractions. From our phones to a buzz in the air that’s always going around, it can be difficult for singles today to give their undivided attention to whoever is sitting across the table from them. Keep the exchange on the shorter side—that way if there’s no chemistry, you can sneak away quickly.

Anxious about going on your first date? Be sure to also check out our Step by Step Guide to Preparing For Your First Date and our Step by Step Guide to Going on A First Date


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