5 Places To Meet Singles (Or Not…)

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I consider myself unique only in that I didn’t get the manual on how to meet girls.

No one taught me anything other than at some point it will magically happen. Even worse, when it does happen, I’ll know exactly what to do, just emulating my parents, and we’ll all live happily ever after.

I will argue that most dating advice is BS, including my own. However, there is one thing that is consistent, it takes effort. I have to create opportunities to meet women, and facilitate the communication necessary to hopefully turn that opportunity into a reality.

So without further ado, I’ll share my thoughts on five places to meet singles that haven’t worked for me.


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I came in REALLY late to the game on both of these things. The only times I’ve been in bars in my early years was awkward for me as I didn’t know what exactly to do. Later on in life, when I started to get a clue, I would go with my guy friends with a specific purpose: to hitting on girls.

No matter what anyone tells you, if you’re at a bar or club with just your guy friends, EVERYONE knows why you are there. As you are awkwardly scanning the room looking for girls to talk to, they’ll start to pick up on it and are immediately put on the defense.

While I don’t have any regrets about going out, it did mess with my psyche for a long time. So much so that I had a moratorium for myself to not go to any more bars, clubs, or “loud, crowded venues”. The only exception to this rule is if I have a reason to be there. Or I am bringing women with me. It’s much easier to start a conversation when you have people who can provide you with a little social validation, and you’re not a total weirdo.


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Ironically enough, I went to one of the first speed dating setups in Chicago. I saw it on television, and I figured it would solve all of my problems, based on what I saw on the report.

However, I was so embarrassed to go, I felt something was wrong with me that I had to submit myself to something like this. So I made up a story that I was a journalist, writing about it for the school paper. The story only went so far, most of the women that were in attendance were older than me. They also tended to shut down or otherwise disengage from the conversation really early on leading to awkward silence for a few rounds.

Later in my life, the same company reached out to me again, occasionally offering me free seats at their events. The problem? A ton of women show up to the events and are paying good money, but the men are few and far between. I went to a free event a few years ago, and there was this really weird vibe. No one was happy to be there, and the same closed off experience I had last time happened again. There was an air of desperation on both sides that was also in place, and I remember people being hypersensitive as well.

If you really want an extreme example of this as well, look up the geek (Comic Con) attempts at speed dating. There are usually only a few guys and a TON of girls.

I avoid these types of events altogether.



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I place a ton of things in this category, whether its Singles Softball, Singles Cooking Classes, Singles Bar Events, Single’s Night Out, Adventure Clubs, et. al. They all have the same fundamental problem of pointing out ‘hey I’m single!’ and ruining most of the interactions. Even worse, they have a hard time recruiting people as well. Most of these events are just glorified bar crawls. If you go in with the expectation to meet someone, than it gets awkward and weird to distract from the event to talk about dating. Vice Versa if you are there just to ‘enjoy’ the event and meet people, the dating part never comes up. And if it does, most aren’t willing to commit to declaring interest or discussing further at said event. You would think about it being a ‘singles’ event would make it easier, but it makes things more complicated than necessary.

Again, I also avoid these types of events and companies.


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Imagine that I told you there are companies out there that are supposedly sitting on a gold mine of future partners. They know so many women and they are dying to meet you. But I have control of the list. And for a small finders fee, I can bring them to you and they will be more qualified than anyone you could find on your own!

That is most of the premises of many of these type of services. Whether they are Matchmakers, Professional Wingmen or Wing girls, Party Hosts, et. al they all fit into the same category. The problem with most of these services is that the idea is great, but the premise is flawed.

Most of the time, the clients they have are the most difficult to find a mate for. Either they have really out-of-place expectations, they’ve been hurt before, just out of a divorce, you name it. Trust me, I worked for one of these companies and it appalled me what clients we ended up dealing with. I also went on a date with another service, if you want to read my harrowing tale. I can tell you from experience, your perfect match isn’t walking through the door anytime soon. She’s not going to shell out the cash when cheaper and more bountiful options are available. The high-end services can reach into the 5 figure range, and those folks really are just looking to trade their money for a relationship. It’s not a good look either way.

Most of what you can do to avoid these kind of services is to do exactly what the do to find candidates. Have a social life and make it a habit to meet new people. They don’t cold call for candidates.



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There are a ton of online dating sites. And I’ve been on most of them. There are the mains, Match.com, OkCupid, eHarmony. There is the aforementioned Tinder app. And there are the niche sites as well. Most of the niche sites suffer the same fate of not being able to recruit a number of good candidates to the site, leading to fake profiles and bots running rampant. It takes a while for any of these sites to gain steam, and usually it’s under a realm of controversy. And let’s not talk about Craigslist’s bot problem. I’ll never post there again due to the massive amount of spam one receives.

I wrote most about my experiences with online dating here, specifically targeting OkCupid. But the summary is that I know the women on the site are being bombarded by messages. It’s hard for women to sift through the litany of bad messages to focus on you and you alone. And even if you do pierce the veil, you still need to make the effort to meet and screen her in person in order for it to be legit. I don’t trust what I see online until I can see and talk to her in person.

The other unwritten rule is that if your real life sucks, than online dating isn’t going to be a solve to your problems either. Most people use online dating a substitute for having a social life. But I would argue that it impairs your ability to interact with people, mainly because of the ubiquitous nature of online dating. In fact, some are calling for people to put down the apps and go out and meet people the old-fashioned way.

I’ve always treated online dating as kind of bonus round, as it were. I have not once yet met someone for a long-term relationship off any online dating website, so my expectations are kind of low. It does provide some convenience and shortcuts, but there is no shortcut for life or social skills.



Next time, I’ll divulge the secret sauce and tell you what HAS worked for me, and most of it is Chicago specific.


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