What does it take to succeed in dating?

Photo by Justin Follis on Unsplash

What do you consider to be a measure of success in dating? Is it finding joy in your dating life? Finding a partner (or partners)? Maybe it’s a bit more substantial to you, like getting married, settling down, and having children.

To me, success in dating means 1 of these 2 things are true about your love life:

1. I have what I’m looking for


2. I’m happy with my dating life

I consider myself successful at dating. I have a wonderful relationship with a wonderful woman, and I’m happy with our life together. Truth be told before I met my partner I considered myself successful at dating.

I was happy with my love life before we met, and that alone was enough to feel like a success. I may not have had what I wanted, but at the very least I was happy with my dating life. Obviously, it’s better to have both, but one was enough to feel successful…I just feel even more successful now because I really lucked out.

If your bar for success is higher than that, that’s completely fine, I just disagree with your measure of success, and I think you should adjust your thinking a bit. Success in dating is all about dating the way you want to date and doing it in a way that makes you happy.

You can be successful at dating if you go on an occasional bad date, and you can still succeed at dating if you find what you’re looking for, enter into a relationship, and see that relationship end on good or bad terms. Think of it like being a professional athlete. Even if you lose an individual game in most people’s eyes, you’re still a success because you’ve successfully made it to the top of your field.

Enough chit-chat, let’s get down to the heart of the matter. I’ll take two approaches to the question: What does it take to succeed in dating? AND What does it take to succeed in online dating?

While most skills you need to succeed in dating are applicable to online dating, some aren’t, so I’ll tackles online dating specific skills first.

What does it take to succeed in online dating?

1. Basic skill at building a decent dating profile

It doesn’t take much to build a basic, dating profile. I can promise you that, but I can go one step further and tell you how to do it. If you’re skeptical about the need for a decent profile to succeed in dating, trust me when I say that it’s better to put in minimal effort into your profile early on and not have to redo it, than try online dating for a year with a bad profile. Your results may vary, I know plenty of people with bad profiles who met someone online. Having a decent profile helps, it’s not a cure-all, but it helps and it really takes very little effort.

2. Basic skill at sending and responding to messages

This is another one of those things in online dating that, while it isn’t necessary, it’s pretty helpful. You don’t have to send a great first message or be particularly amazing at sending and responding to messages, but basic skill will go a long way. So, here are some basics:

  • Say more than “Hey”, “Hi”, or “Hello”
  • Your first message should never be more 500 words. I’ve heard varying ideal message lengths ranging from 125 – 250 words, so somewhere between, there may be the sweet spot
  • Ask them about something on their profile. It’s a good idea to ask about anything that is a conversation starter on their profile
  • Avoid asking about, or making a statement about them that is generic
  • Don’t ask them why they’re single
  • It’s okay to banter, but remember to ask something substantive
  • Avoid overtly sexual conversations

Beyond that, all you really have to do is not be a terrible person and you’ll do just fine.

Now, let’s tackle what it takes to succeed in dating in general:

What does it take to succeed in dating?

3. Put yourself in a position where you can succeed

In order to succeed in dating, you need to have the opportunity to succeed in the first place. If there is some reason you can’t date, or can’t date the way you want to date, you won’t be able to succeed. At the very least, your first step to dating success will be putting yourself in a position to succeed.

For me, that means having a certain amount of disposable income, a certain amount of free time,  and most importantly, a positive outlook and the belief that it’s possible to find what I’m looking for. Whenever I was at a point in my life when I had none of those things, I wasn’t successful in dating.

What does it mean for you to be in a position where you can be happy with your dating life and/or find what you’re looking for? Whatever that might be, whether it’s a question of income, work-life balance, or finding child-care, you should figure out what you need, and try to get it.

4. Know what you want and know what you’re looking for

What do you want out of dating? What are you looking for? And more importantly, are the two aligned?

It might seem silly to treat what you want and what you’re looking for as separate things, but assuming that they will be the same is a mistake. I’ve met several people who want one thing but are looking for something else. I’ve met people who want casual sex with as many partners as possible but say that they’re looking for a committed, monogamous relationship. I’ve met people who want a commitment, but only look to date people who have issues with commitment.

If what you want and what you’re looking are at odds, you’ll never succeed in dating. Whatever you want out of dating is valid as long as it involves enthusiastically consenting adults, just make sure that it lines up with what you’re looking for.. Don’t hope to succeed in dating if you want a relationship, but all you look for is casual sex, or vice-versa.

5. Realistic expectations

You know what you want, and what you’re looking for, you’ve aligned the two, so now you have to figure out how realistic the chances of finding that will be.

You should have realistic expectations related to what you’re looking for, what you want, and most importantly, the likelihood of finding all those things. Let’s say that you want something simple: a monogamous heterosexual relationship, with someone you’re attracted to, regardless of their physical attributes, religious or ethnic background.  You can realistically expect that you could find someone like this and be safe in that assumption because you’ve got a very broad group of people to choose from.

Now, let’s add some layers of complexity. You want all the things mentioned above, but you need a partner who is over 6 feet tall, of Asian descent, a Buddhist, and one who has an income over $465,000 a year. How realistic are those expectations? That person might exist, but the likelihood of meeting them is very slim for most people (an annual income of $465,000 or greater places you in the 1% in the U.S., for context).

Take a hard look at what you’re looking for, the criteria you consider to be inflexible, and really consider the chance that you’ll meet that person. If you want to make it more realistic, look at the criteria you’re looking for and consider things from a statistical perspective. A certain percentage of the total population of wherever you live is over 6 feet tall. A certain percentage of people are of a certain ethnic group, religious background, and so on.

If you come to realize that what you’re looking for is fairly rare, you should consider changing what you’re looking for or adjust your expectations. Your mythical Prince, Princess, or Sovereign Charming might exist, but be honest with yourself about the likelihood of finding them, and adjust your search accordingly.

6. Basic skill at date planning

Doesn’t matter your gender or sexual orientation, if you want to succeed at dating, it can’t hurt to have some basic skills at planning dates. You might think this will take a while to cover, but here’s a really basic primer:

  • Pick a place that you’ll both likely be comfortable hanging out.  If you like lounges, and they like lounges, go on a lounge date. If you like lounges but they don’t, don’t do a lounge date
  • Pick a date type you’ll both be comfortable going on. If you think if you would be uncomfortable going on an activity date, don’t go on one
  • Pick a place that is relatively easy for both of you to get to

It’s not rocket science, I promise. It really can be that simple.

7. Follow through

I can absolutely promise you that most of the success you will have in dating is because you bothered to follow through. If you’re interested in someone and that feeling is mutual, follow through with date planning, communicating with them, and working to build what the relationship or situationship you want. If you can follow through with the people you’re interested in, you’ll find that success will just…sort of happen. Oh, and if you’d like to help others become more successful in their own dating lives, follow through and let people know when you’re not interested. Most people will appreciate it.

8. Luck

If you’re thinking yourself “Demetrius, I do all these things, I have all these skills, and I’m still not finding success in dating. Why is that?”, the answer really comes down to luck. You can do all the right things not find dating success, you can do some things right and find dating success, and you can do absolutely nothing right and luck your way into finding the exactly the thing you’d need to make you happy.

It takes work and effort to find success in dating, but those things can’t guarantee success. You’ll need a little luck.

I honestly believe that everything I mentioned above, all the skills and best practices, can lead to success in dating. It did for me, but keep in mind that the success I’ve had comes down to 50% effort, work, and best practices and 50% Luck.

Which is why I always wish you…

Good Luck Out There.

Also published on Medium.