Dating Questions And Answers To Help You Succeed

Updated March 5, 2024by Regain Editorial Team

There are many life skills that schools don't teach you. How to do your taxes, how to buy a house, and how to date. Many adults don't know how to date successfully. While every person is different, there are some ground rules for making a date successful. From when to transition from dating to being in a relationship, to knowing how to determine whether or not you and your date are hitting it off, here are some of the most frequently asked questions for dating, along with the answers.

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Is online dating worth it?

The internet has made it easier to find your soulmate. Thanks to the internet, you don't have to be limited by geography or coincidence to find a good match. You can date more people and match with someone based on your personality and interests.

With that said, there are a few disadvantages to online dating: first, the over-saturation. If you're seeking a long-term relationship, you may have to parse through an abundance of messages from people who are not actually searching for the same thing (but claim they are). If you are primarily interested in dating people who meet a limited set of criteria, you might have a lot of competition to go up against. Don't put all your dating eggs in one basket. Try going to places where there are more like-minded people, such as conventions. Use more websites than just a dating site. Online dating can be worth it, but it's one tool out of many.

When should I ask them on a date?

If you're talking to someone, especially on an online dating site, time is of the essence. Because online dating pools pair like-minded people (or geographically-close people), you are likely not the only person reaching out to the person you’re interested in. If you wait too long to actually ask the person out, you may miss out. If you ask too soon, however, you might find yourself on an awkward first date without much to talk about. There is no magic time, but you should ask as soon as possible if you two have a great conversation.

How do I avoid getting stood up?

The idea of getting stood up sounds nightmarish. You talk to someone for a while, get a date set up, and when the time comes, they're a no-show. We live in a society where people don't want to admit that they got cold feet or met someone they connect better with, so they don't cancel and make you stand around.

The truth is, there's no way to avoid getting stood up. People are going to flake out on you. Have a backup plan, recognize that it says more about the person who has stood you up than it does about you, and don't wait around too long.

Where should we go?

When it comes to dating, the first date should be someplace open and public. It gives both parties a sense of safety, and you can easily leave if the date goes sour. Restaurants, malls, coffee shops, parks, and any other open place should be good. It depends on you and your date's tastes.

How can I tell if they like me?

When dating someone or just talking to someone in general, it's hard to figure out if they like you or not, especially if you're not good at nonverbal communication. It's easy to mistake someone just being nice for someone being flirty.

There is no correct answer, as people express love differently, but many people use a few signs. Obviously, if someone is flirty, they probably like you. They may tease you, use eye contact more, smile, and pay attention to what you're saying.

Some people will just straight up admit they like you, but for many, the fear of rejection prevents them from saying so quickly and easily. One of you has to say it at some point, so if you like the person and see subtle clues they like you back, say it. The worst they can do is say they do not feel the same way.

How can I tell if they don't like me?

When someone doesn't like you, they may try to give subtle clues to tell you to go away, but the problem is that some people don't get the hint. On a date going bad, the person may be quiet. If the person is more interested in their phone than you, it could be a problem, as well.

Perhaps the biggest hint that the date went bad is the sudden flake. If they say, "Sorry, I have to go," and offer a wafer-thin excuse, then they may be leaving gracefully, so they don't hurt your feelings. While some people have a legitimate excuse, it could signal that the date went bad if they don't text you later.

Many of us wish we lived in a world where people would be more direct, but everyone is afraid to say what's on their minds. To understand where your date is, you must communicate effectively and pay close attention to nonverbal clues and body language.

How do I avoid the awkward silence? 

When it comes to first dates, it can be awkward for both of you. Not everyone can befriend strangers. Think of some conversation starters beforehand. Ask about hobbies, family, aspirations, and so on. However, don't prepare a series of questions like it's some kind of interview. Keep it casual and interesting.

Also, if they expect you to be smooth and flawless on your first date, then they're probably not for you. First dates come with nervousness and ups and downs in conversation; no one is perfect.

Who pays?

There is no straight answer to this one, but a good rule of thumb is that the person who set up the date and chose the place should offer to foot the bill—or you can discuss splitting the cost before/during. It’s helpful to go with the flow and communicate with your date. 

When should we kiss?

The first kiss is a dating trope as old as time. It can seal the deal or make things extremely awkward. In a perfect world, we would ask if we could kiss them beforehand, and if they say no, it'd be no big deal. Many of us feel scared of asking directly, even though we know that consent is an important part of romance and dating. So, when should the first kiss happen? First date? Second? Third?

It is usually best to wait until the end of the date, in case the kiss does not go as planned, or the chemistry is off. It is also important to receive your new flame’s consent before initiating contact. If they politely decline, don't get hung up on it. While some people will naturally gravitate towards one another, you should never force a kiss on someone. Consent is key.

How do I stop dating without hurting the other's feelings?

So, you went on a couple of dates, and while they weren't terrible, you realize that the person isn't for you. How do you conclude your dating relationship with that person without upsetting them?

In most cases, you're not going to end up breaking up with your date without causing some negative emotions. They invested time into dating you, and maybe they like you, so they aren't going to walk away without at least some kind of disappointment.

In most cases, being honest is the best way to do it. Ghosting them, where you cut all communication with them, is just going to leave them confused and upset. Keeping it open-ended ("I found someone else") isn't a good way to do it, either, because they may feel hopeful that you will change your mind. Just tell it like it is. Don't be overly negative or critical, however; reinforce them by listing all their pros but give out a few reasons why it didn't work.

You're not going to end the date without them being somewhat upset, but being honest is the safest—and most respectful—route.

When does it go from a date to a relationship?

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So, when do you go from seeing someone to being in a relationship with them? As is the case with most of these answers, there is no exact time. You should not rush things if you or the person you're with aren't comfortable with being in a relationship just yet. Both of you need to desire to take it to the next level, and if one or both of you are not yet in that place, it won't work. The best thing is to ask for a few successful dates.

Listen to your instincts and try having open and honest communication about what you're both looking for and want.

Seek help

If you're having trouble with dating, there is no shame in getting yourself a mental health professional through Regain who can help you navigate the dating world and work through any challenges for you in dating or relationships. Regain offers convenient, and affordable sessions with licensed therapists and relationship counselors.


The world of dating can be intimidating, but through guides like this one—as well as support from a therapist— you can work through any worries to put your best foot forward and find the right person for you.

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