A Shrink’s Take on Dating: It’s Supposed to Be Fun

Avrum G. Weiss
5 min readDec 26, 2017


I’m a clinical psychologist, and over the years, and I’ve had a lot of opportunities to work with people who are dating, either for the first time, or the first time in a long time. People generally describe dating as a miserable experience and approach it with emotions ranging from anxiety to terror. In fact, I’ve had a number of people tell me that they’ve stayed in bad marriages for years because they dreaded dating so much.

A lot of dating advice seems to be taken from the “How to Be Popular in High School” manual. There is usually a lot of over complicated tips for how to present a façade that will get people to like you. Following this advice, people obsess over writing the perfect profile for a dating website, or picking something to do for their first date that they think will really impress their date. In contrast, the most important thing I’ve learned about dating, and the thing that people most often overlook is very simple: just be yourself.

Dating is not a popularity contest; the objective is not to go out with as many people as you can or get as many people to like you as possible. The purpose of dating is not to impress someone, it’s not a job interview. The objective of dating is to find one person you like, preferably someone who also likes you, and then spend some time together to see how things go. Dating is about discernment, not popularity. The idea is not to get someone to like you, but to figure out if you like each other. If you go out with someone on a first date and things don’t click, that’s a success, not a failure. Trying to impress someone to get them to like you creates the same problems as trying to impress an employer to get a job. If you succeed, then you have to continue to pretend to be someone you are not. In the long run, you are better served being yourself and letting the chips fall where they may.

Here are some of the most important things I’ve learned about dating:

  • Date a lot of people casually, and then one person at a time seriously. Don’t spend a lot of time chatting online, texting, building up to a phone call, etc. None of that really helps you get to know someone, and it creates way too many opportunities for you to talk yourself out of meeting someone for purely imagined reasons. No matter how much the technology improves, there is still no substitute for good old-fashioned meeting face-to-face. It’s still the most reliable way to tell if you and another person will connect. If you have any interest in someone, don’t waste a lot of time trying to figure things out. Go ahead and meet them for coffee and see what happens.
  • Don’t obsess about when to text or call someone, whether it’s too soon and you’ll look needy, or how long you should wait, etc. Keep it simple. If you want to talk to someone, call them. If you don’t, don’t call them. Hopefully they will use the same straightforward principle with you, and then it’s very easy to figure out where they stand. If they call you, you know they want to talk to you. If they don’t call, you can be pretty sure they are not that interested in talking.
  • The criteria for going on a second date with someone is whether you had a good time on the first date. Again, keep it simple. If you enjoyed yourself see her again. Don’t worry about whether she’s been single long enough, or too long, or she’s not into you enough or too into you, or too old or too young, or whatever other arcane criteria you’ve been using for dating. Keep it simple, if you had a good time, see her again. If you didn’t have such a great time, but it was at least pleasant, and your intuition is that things might go better the next time, then go ahead and see her again. People are often very anxious on a first date and don’t put their best foot forward. If you hope to be in a relationship with someone for the rest of your life, then what you are looking for is not how they are right now, but how they change and adapt over time. This is a long-term investment you are considering, so see here again and you may be pleasantly surprised.
  • Believe it or not, dating should be fun. Suggest things to do that are fun, things you like to do, not things you think the other person might like. If you suggest something fun that you like, the chances are better than you will be more relaxed and let more of your true self show through. Having coffee is fine for a first date, but it’s a lot of unnecessary pressure to have date after date where all you do is sit and talk with each other. Get out and do something fun, something silly where you get a chance to let your hair down and get to know each other in a variety of ways. Dating is a part of your social life, it’s not a job. If dating starts to feel like a job, you probably should take a break and spend more time with your friends.
  • Think of dating as a great way to learn more about yourself. Every person you date gives you very helpful information about yourself; what you like and don’t like, what works for you and what doesn’t work. Dating also gives you lots of opportunities to speak up about what doesn’t work for you, and if you are divorced, this is probably something you could use some practice with. Dating gives you lots of chances to say “no thank you” to people when a relationship isn’t working for you, without feeling like you have to make up a lot of extraneous excuses. Ending a relationship because it’s not working for you is the only reason you need to end a relationship, and when you get down to it, it’s really the only reason people end relationships.
  • Keep in mind that the goal of dating is to one find one person you think you might have a future with (unless you are looking for multiple partners, but that’s a subject for another column). I find getting to know one person intimately at a time to be all the challenge I need. The thought of doing that with two or more people at the same time is overwhelming. When you find someone you like, someone you think you may have a future with, let them know you want to have an exclusive relationship so that you can see if there is a future.

I hope some of these tips were helpful for you. If you have questions please feel free to leave a comment at the end and I’ll respond.