Stop Dating, and Start Meeting Interesting People

It’s not about relationships (as you know them)

Every day people post descriptions of themselves on dating sites, go to networking functions, get introduced by mutual friends, head out to bars, go to church events- all with a similar goal in mind: To meet someone that could be a life partner. The business of finding a significant other is big business. The usual process is to connect somehow, check the other person out, go on dates, and then, if everything seems to be going well, to start a relationship.

There’s only one problem with this process. Most people aren’t very comfortable with one or more aspects of the dating model. Maybe you’re shy and can’t get to the first stage. Maybe you’re so picky that you can never find that exact match you imagine would be perfect. You might be so focused on not being alone that you appear desperate or needy. You might have bad judgement when it comes to vetting a potential partner.

This article aims to change all of these approaches to meeting people. You won’t be going on too many of those dreaded ‘dates’, at least not for a while. And when you do it will be because both of you have decided to try something a lot more intimate. By that point you’ll have a whole different idea of what a relationship is and whether you really want or need one. You’ll know a lot more about yourself and the people you meet will be a lot more interesting. You’ll also know how to spot potential problems and how to recognize that spark that is critical to any successful long term relationship. And you’ll have fun in the process, a lot of fun. And you may never have to go on a ‘date’ again!

The Goal: “This was a great conversation- let’s do it again!”

That’s the goal: A conversation where both people have fun, learn something, find a shared interest etc. The kind of conversation where both people want to continue it. The goal is not a date, a marriage, a meeting with a soulmate- it is to start a connection, a connection that might start the process of expanding your life.


One of the things I’m going to talk about is rapport, that mysterious connection that is the key to making friends and starting relationships. What is it and is it something you can learn? Let’s imagine you’re at a noisy party and you want a little quiet. You go outside to a patio and sit down for a minute to collect yourself. You notice that you’re not the only one with the same idea- there’s another guest out here, someone you met briefly but didn’t know before. He or she, it doesn’t matter, rapport is universal, says “It’s nice and quiet out here- I was having fun but I needed a break.” You respond that you felt the same way. This is moment when you have a brief opportunity to establish rapport, a shared sense of being connected if only for a moment. Both of you have the opportunity to strengthen that connection just a bit with a little small talk, perhaps comparing notes about how you each know the hosts, or offering to get a drink for the other person.

This is not about relationships, the future or anything else. It’s just about making a connection that is positive. If you try to go further without such a basic connection it won’t work. You’re not aiming to be besties, lovers, or grow old together. Instead you’re adding to your circle of acquaintances, acquaintances who may eventually become friends. This is how relationships begin- gradually. Sometimes they reach the point where they accelerate but they seldom shed sparks from day one. Start with a little basic rapport-building, find some kind of common ground and be patient- if it’s meant to be it will happen.

I’m writing this to help you slow down, figure out what you really want and meet people. It is not about walks on the beach or LTRs (Long Term Relationships). When you start out by announcing you are seeking a LTR, you’re probably scaring away any real potential partners. Let’s start with the idea of ‘dating’.

No Dating?

I have nothing against dating services like, eHarmony, OKCupid, or Plenty of Fish. In today’s hectic world they can help people find like-minded people. I just don’t think they should be called ‘dating’ services. I think they should be called ‘meeting’ services. It’s a lot easier for everyone if we think of our goal as meeting people rather than finding dates. So rule number one: No dating. Your goal is to meet someone and learn something about them. I’m not saying you won’t go out to dinner with them eventually. That’s fine but it should be a part of the natural progression of getting to know someone, not an activity fraught with all kinds of heavy, unspoken implications.

I’ll start with a story. I met a woman while staying in the same hotel. We talked over drinks with the bartender one night. Later I noticed she was eating in the hotel bar every night even though there were several good restaurants within walking distance. I asked her if she’d tried any other places and mentioned a few. She said she had not and I realized she wasn’t comfortable going to one alone. So I asked her if she’d like to try one the next night. She said yes and we had a nice dinner together. Was that a date? Not by my definition and I don’t think she would define it as one either. Neither of us had any kind of agenda except enjoying a different restaurant and getting to know one another a little better. It was fun and there was no expectation beyond that.

It’s important to note that she had spoken with me several times and seen me interacting with the staff in a first-name, friendly fashion that probably helped her feel secure about carrying the conversation to the next step.

My point is that there is a natural progression in getting to know people. When a person is lonely, needy, or in a hurry to make something happen too soon, they’re putting themselves and the other person under pressure. That never leads to a healthy relationship. So your first goal is not a date, it’s meeting interesting people.

Being Yourself, Knowing Yourself

What does it mean to know yourself and what does it have to do with meeting interesting people? First of all, you need to know what makes you an interesting person. Everyone has something interesting that they do, think, or know about. In some cases the interesting thing may be looks, money, or physical attributes, however that is seldom enough to sustain a relationship. So if you’re entirely focused on appearance and material things, you’re not going to do too well. So how do you focus on the parts of you that people find interesting?

Think about your close friends and family. What are the things you’re talking about and doing when you’re all having the most fun? Sports? Discussing politics (that is a sport in my family, a contact sport!) or ideas? Cooking and entertaining? Building a business or finishing an interesting project together? Look at what you bring to the table when the conversation is the most rewarding. That’s part of what is interesting about you. Think about it because showing your interesting side is a big part of attracting other interesting people.

Knowing yourself is the tougher exercise. No-one is interested in weakness, self-absorption or ignorance. And, frankly, the way you take care of yourself is a big contributor to meeting people. Even if you are self-conscious about your appearance, for example, showing you have self-esteem by wearing clothes that you look good in and working on nutrition and exercise are great indicators that you’re working on yourself.

Taking inventory of your positive ‘interest points’ gives you a basic platform for carrying on a conversation that adds value for both people. This conversation is way more important than imagining ‘long walks on the beach’ or your LTR (long term relationship) dreams. The conversation is the one that ends by both people saying “It’s been really great talking to you, I really enjoyed discussing (learning about, laughing over, etc)…Let’s do it again”. Bingo, you just made a connection. And it starts with knowing yourself.

What if I’m boring?

So what if you’re not coming up with a lot of interesting things people associate with you? It’s time to face facts: You need to expand your life on all fronts. You may think a relationship is the answer but the fact is that a successful relationship is based on multiple shared interests. If you don’t bring an interesting life to the table, you’ll be on the sidelines during the conversation.

Discovering that your life needs to expand is not a bad thing, it’s a very important revelation. So how do you change this? First think about things you were passionate about in the past that you’ve let go. Are there interests you can dive back into? Or what about things you’ve always wanted to do but didn’t? The fact is that anyone determined enough to do something can do it. Skydiving? Writing a book? Acting? Learning to golf? Starting a business? Ordinary people try all these things everyday. And you know what happens? They become a lot more interesting to others.

The great thing about expanding your comfort zone into new areas is that there are other people who are doing the same and you automatically have a shared interest and experience. Skydiving club? Writer’s group? Fellow actors in a play? Your beginner’s foursome? Your customers, employees and vendors? These are all great situations to meet interesting people and you have a perfect starting point for a mutually rewarding conversation!

Get Out of Your Comfort Zone

Expanding your interests and meeting new people inevitably means getting out of your comfort zone. People who always do the same things in the same places with the same people are not very likely to meet anyone different. How could they? They’ve fenced themselves in. If you find that this is a description of your life then you need to do that reevaluation of your priorities and interests that we looked at a few paragraphs ago. Be forewarned, you may meet resistance from your ‘friends’ who are in the fenced-in area. When someone tries something new it often causes those who can’t change to go on the defensive or try to talk you out of this ‘crazy’ new thing and these ‘crazy’ new friends you’re meeting. Consider this a good sign that you are on the right track. Those who try to convince you to stay the same are not the interesting friends you’re seeking. Those who support your efforts to expand your life are your true friends. So get out of your comfort zone- the most interesting people seldom have ‘comfort zones’.

Don’t Travel in Packs

For a lot of people the thought of going out alone is very uncomfortable. This is particularly so for many women because of feeling like a target or a possible victim. I understand this but it is much harder to connect with someone new if you’re traveling with a pack of close friends or co-workers. Choosing safe, well-lighted public places with lots of people around helps. If you do bring a friend make sure he or she understands that you’re interested in meeting interesting people if the opportunity presents itself. The way to handle this is to not spend the time talking about subjects you’re both intimately familiar with like shared family or friends, gossip, work, etc. Even if someone is interested in joining you, these topics form a gateway that blocks a newcomer from participating in the conversation.

Good topics include things like newsworthy events, community stories, interests like movies and music, discussions about the restaurant you may be in, etc. These topics all have easy entry points where strangers can share knowledge or opinion without feeling they are intruding on a private conversation. If you’re not comfortable with a stranger intruding on your conversation you can always go back to your personal subjects, signaling that you are not interested.

Don’t go out with groups of three or more if you really want to meet new people- it forms an impenetrable barrier and, even if you do meet someone, there are all kinds of social judgments and dynamics going on that can prevent any kind of meaningful connection.

Tips on going out by yourself:

  • Avoid places with television sets. TVs in nite spots and restaurant bars are there to keep lone eagles comfortable. There is always a lot more interaction in places without these distractions. The exception is if you are a big sports fan- your sports interest is common ground for conversation with strangers while watching a game.
  • If you have friends who work in the business (restaurant/nightlife), let them know you’re coming in on your own. They can have co-workers keep an eye on you.
  • If you’re leaving by yourself and you’re not sure you trust someone you’ve met, always ask the staff to walk you to your car.
  • It’s actually better to ask for the other person’s contact information without volunteering yours, at this stage (more about this later). The ball is in your court and you can choose not to respond.
  • The first times you go out alone, arrange for a friend to meet you an hour or so after you get there. This gives you a chance to try going solo and a means of ending an unwanted conversation. If you’re having an enjoyable one, just introduce your friend and include both people in the conversation.

High School Dance

I learned an invaluable lesson, as a freshman in high schoo,l about meeting people, in my case, people of the opposite sex. I was a skinny guy with goofy glasses and the worst haircut imaginable. A true geek. We had dances once a month with live bands and I loved to dance. High school dances are true social pressure cookers with hormones raging and a room full of people with limited social skills. I would get up my nerve and ask a girl to dance, get shut down, and then try another (always the ‘pretty/popular’ ones) and get very few dances. After a couple of months of this I was fed up and came up with a brilliant scheme: I would methodically ask every girl to dance, regardless of looks or social status. It was hard but a lot of those unpopular girls were grateful and danced with me. Some of the popular girls did too, after they saw that I really liked dancing (and girls!).

The lessons learned were huge. First, I met a lot of people who became friends. I got over my geekiness (and that haircut) and learned self-confidence. I also learned that if you let rejection become personal you will be crippled when it comes to meeting people and making meaningful connections. Rejection is almost always about the other person rather than you. Don’t take it personally (this is true about practically everything in human interaction!). And a lot of those ‘unpopular’ girls grew up into pretty special people.

Finally I learned some lessons about persistence- if you want to expand your horizons, you have to expand your comfort zone. The great thing is once you do it, it stays expanded!

Lines vs. Conversation-Starters

Pick-up lines exist but most are ridiculous. However there are ‘conversation-starter’ lines that do help. I learned this from a guy at a club years ago who was constantly hitting on girls with a lot of success. I asked him his secret and he said he had the perfect line. I asked him (of course) what it was and he said:

“Where are you from?”

I laughed it off but he was persistent. He said it was perfect- if they were from some other town you could ask what brought them here. If they were from here you could start comparing who you know in common or where you work, etc.

I thought this was too easy. So I picked a girl, walked over and asked where she was from. And we went right into a conversation (she was local). Just like that. Then she said, “I’d really like you to meet my husband…”. They are still friends of mine and we laugh about the ‘line’.

The point here is this wasn’t a pick-up line, it was a conversation-starter. It allows two strangers to find some common ground to start to get to know each other. And if someone says “none of your business” and you are feeling persistent, you can say “sorry, I just hadn’t seen you around here before” or “I just moved here and I’m getting to know people”. Or you respect the fact that they’re not interested and move on with a quick “sorry to bother you”. Don’t take it personally, it’s probably something like a partner, a bad day, or shyness.

Don’t Hit on People in the ‘Industry’

Don’t view people who work in the nightlife as potential partners when they are working. Bartenders and servers constantly deal with lonely, shy, or just plain nutty people who are looking to spend time with their ‘friends’. Don’t think that because they are friendly and serve you drinks that you are special. They have to be friendly and accommodating- that’s their job but it doesn’t mean that they are available. In fact they are not- would you walk into an office everyday to talk to the Receptionist? No, because she or he is in their workplace. It’s no different for those in the ‘industry’. With time you may develop friendships with industry people but it has to be on their terms. Like any other example, this comes about because of shared interests, interests outside of the workplace. However, that is their call.

‘Googling’, Facebook, and All That Other Stuff

If you’re meeting someone for the first time and they don’t have too common a name, I suspect you’ll have ‘Googled’ them, i.e. checked them out on Google, Facebook, LinkedIn, Twitter or wherever else there might be some background on them. I recommend this. And if they have a common name, add something you know about them to the search query like geographic location, company they work for, mutual friend’s names. This might help zero in on them. The primary purpose for this research is to ferret out anything potentially bad.

Having said that, assume they are ‘Googling’ you. So make sure you Google yourself once in awhile so you don’t get any surprise knowledge about you dropped into your conversation. This also helps you anticipate any conclusions they may have made about you and be prepared to deal with them.

Oh and by the way: We live in a public world these days whether we like it or not, so think twice before doing something stupid that could end up in your ‘permanent record’!

Dating Sites, Speed Dating, and Blind Dates/Fix-ups

So, I’m this far into this and I haven’t gotten into Match, eHarmony, trends like speed dating, or blind dates, AKA ‘fix-ups’. That’s partly because this article is really about what happens before you get to the dating stage, the personal assessment and practice you do to become comfortable meeting people and to keep the connection interesting for both parties. Dating services are a way to meet people but until you discover your own interesting side you won’t attract interesting people. Once you do start to understand why someone would find you interesting you have a basis for creating a profile on a dating site, a profile that really tells the story of who you are in a way that captures interest. I don’t recommend writing a long litany of what you want and don’t want- you’re writing yourself into a corner and severely limiting the types of people you may meet. Remember, the goal is not a LTR at this stage, it’s a conversation. Once you’ve had that conversation both parties assess the outcome and next step if any. So use the dating site to meet people, understanding that that is all you want from it at this stage.

Some Tips About Dating Sites:

  • Photos are a must. More photos equals more interest. Photos must be current (if you get together they’re going to see who you look like now, not what you looked like five years ago!). Don’t include photos with other people in them. Photos should not just be headshots; include some with you outdoors or doing something interesting. Guys, do not post shirtless images or you posing with dead animals- I guarantee you that these do not go over well!
  • When you write about yourself, focus on things that others will find interesting. This seems obvious but a lot of people write the same things (long-walks-on-beaches type of things. Who doesn’t like long walks on beaches? But it is boring…).
  • 99% of the time the person reaching out (in a heterosexual pair) online will be the male. This means that women are writing sales copy and men are shopping. This may not be fair but it is true. Fortunately, you don’t have to respond.
  • Take a friend when you go to meet someone. Arrange a signal for them to leave if you feel comfortable.

Blind Dates and Fix-ups

Blind dates are dates where someone you both know decides you are compatible and should be thrown together. This is inherently a bad idea because it is up to the two people involved to make that choice. Don’t get roped into this situation. If a friend wants to connect you to another person you’ve never met, it should happen at a social situation like a party or larger gathering (not a double date- this really puts the pressure on and you won’t really get to figure out if there is a connection). There should at least six people around and hopefully the other four are not all long-term couples.

Be Informed, Interested, and Informative: Adding Value

Ultimately this article is about initiating and enjoying conversations with strangers, conversations that may expand your world and theirs. If that expansion includes romance, so be it, however it’s perfectly alright if it expands into other things like your range of interests, knowledge and activities. The key to achieving this goal is to bring something to the table every time. To add value to the other person’s existence.

Being well informed about the world is a good start. Showing real interest in the other person (by actually listening and engaging them) is an incredibly powerful stimulant. We all like attention.

Generosity = Listening

The truly great conversationalist is a truly great and active listener. Paying attention and listening should be viewed as an act of generosity. You’re giving the other person the gift of your undivided and sincere attention. The ‘active’ part comes from helping the person move their thoughts along. This is done by encouraging or curious statements like:

“And what was the result of that?”

“How did you feel about that?”

“That’s wild. Then what happened?”

Think of a situation in your experience that has similarities to the story they are telling so you can have an aligned conversation, one where there is real back and forth.

Unfortunately one of worst and most common situations while dating is being with someone who constantly talks about themselves or is fixated on one subject. This usually is the result of insecurity or shyness but it is a deal-killer. That’s why starting out gradually with an aligned conversation rather than a date is important. For one thing you can always end a one-sided conversation whereas going on a date usually means seeing it through until the bitter end.

If It’s Not Happening

Most people know really quickly whether there is any kind of connection going on. If there is not, and you’ve meet via a dating site or even a friend’s fix-up, just tell the person that this is not working for you. Then go. Brutal? Not in the long run. What’s brutal is not dealing with it right away.

Means of Contact (calling card)

The sharing of contact information is a touchy subject, especially phone numbers. My feeling is that until you’ve established a connection with trust you should not give out a phone number. Anyone can get a fairly anonymous email address for free via Gmail and then choose to Reply or not based on the type of communications you receive. This gives you a filter for stalkers, obsessive types, and other jerks. Although you can block numbers on most cell phones, I’d hold off on giving out phone numbers.

I have one friend who is very cautious- she gives out a fake first name when she first meets someone. This backfired when she was out with a new friend and ran into co-workers who called her by her real name!

I like the concept of a calling card as it’s easy to get an email address or phone number wrong when writing it down. Mine has my name, phone number, website and email (no physical address) because I use it for business purposes too. So I don’t give it out unless I’ve made a connection. Given that I’m male, I’m somewhat less worried about stalkers since, for some reason, most tend to be male.

The card should, ideally, not be your business card because mixing business and your private life doesn’t work and, should you have a problem with the person, they know where to find you. You can get a simple card done online for a few dollars.


So you have a phone number or email, now what? Give something and don’t ask something. This means calling or emailing and offering a thank you for a great conversation. If there is information or a favor you can do, do it. Wait for feedback and if it is positive, schedule another conversation.

Expanded Circle of Friends

Which brings us to our real goal here: expanding your circle of friends. That’s right, I’ve been leading you along pretending this has something to do with relationships. Relationships start by expanding your life and the way you expand your life is by expanding what you do and who you do it with. A lot of us establish friendships early in life and seldom add new friends as we get older. Yet adding new interesting people to your life is the key to solving the relationship riddle.

Think about it like this: we seek relationships because we’re lonely or we want someone to share life with. Being stuck in one place limits your choices which leads to the need to connect. If you don’t break out you’ll continue with the life you have. Even one new friend can expand everything you’re doing. Having several new friends, even if they don’t turn into partners, multiplies that expansion exponentially.

I like to think about it like a dinner party where half the people know each other and half only know the hosts. By the end of the evening everyone will have met someone from outside their familiarity zone. The web of connections has expanded and if you are a guest you may come away from a new conversation with a window into a whole new set of relationships, assuming you follow-up with your new acquaintance. And guess what? There might a spark lurking out there with your name on it. The chances are certainly much better at this point.

What’s Love Got to Do With It? The Spark.

It’s my feeling that any two people should not escalate a relationship beyond a certain point unless there is a mutual, unmistakable spark that is sustainable. If one or the other works at it, even with the best intentions, it probably won’t last. This may seem discouraging- after all sparks are not a common occurrence. That’s why the concept of expanding your circle of friends with interesting people is so important. Do the math. If you stay in your comfort zone you’ve exhausted the probability of meeting someone and having that strong connection everyone wants in their life.

We live in a web of social networks: Family, friends, co-workers, people we went to school with, people with shared interests, friends on Facebook, etc. Even a small expansion of your network by connecting with someone completely new connects you with a whole new range of people via their networks. So even if there is no powerful mutual spark, there is much greater likelihood of you meeting someone out there who is the real deal.

So, stop dating and start meeting interesting people!

Former software marketer. Former musician. Writer, nine non-fiction books, two novels, Buddhist, train lover. Amateur cook, lover of life most of the time!

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