The philosophy of successful dating: how to turn the odds in your favor

I’ve come to a rather interesting and pleasant place in my journey into singledom post divorce. I’ve basically figured out what works for me: I no longer have any issue meeting or dating women I’m attracted to (both mentally and physically)–at this point, it’s simply enjoying their company and searching for [special one]*.

* Yes this is a George Saunders reference for those literary nerds out there.

As you know if you’ve read, I never get into anything too personal–especially when it comes to the women I date–because I respect their anonymity…

But there are other reasons I’ve been writing fewer Manchild posts as of late.

The first reason is that as someone who’s doing it earnestly, dating is time consuming–I simply haven’t had as much time to write. However, the larger point is that I find I don’t have much more to say.

What I can offer now is a general theory of dating that I think works pretty well. We’ll take this in steps, but I want to start with the most effective mental frame to have while dating…

The Dating Mindset: Be as Open as Possible

People are not products. We are not a list of qualities and descriptions and specifications. We are not a resume. And yet a huge proportion of singles treat prospective partners this way.

The truth? The success of any relationship that lasts more than a month will depend on three very simple things.

  1. Do you have fun together and enjoy spending time with this person?
  2. Is there sexual chemistry, and when the time comes, is the sex good? (remember that the first time is not usually going to be mind blowing, and don’t make good the enemy of great — good sex is better than no sex)
  3. Do you care about this person as a human being?

Note some of the bullshit, arbitrary things I did not list that people often use as qualifiers/disqualifiers: age, divorce, kids, finances, pets, whether or not they like fishing, hunting, are vegetarian, vegan, Hindu, Christian, agnostic, liberal or conservative, etc.

Now if those things prevent them from answering yes to the questions above, it matters — but ultimately it’s your interpersonal connection and sexual attraction to the individual that’s going to determine the success of any relationship. The rest is window dressing.

In other words, the more non-negotiables or preconceived ideas you have about the type of person you’re going to date, the more likely it is that you will not find what you’re looking for in the modern world of dating, because at the end of the day those things just don’t matter that much.

To use myself as an example: in the past six months I’ve dated a plastic surgeon, a single mom/esthetician, a punk rocker, an aspiring pop-star, a high-powered lawyer, a single mom/banker, a grad student — I could go on, but the point is that these women couldn’t be more different, and guess what?

It didn’t matter.

In every case we had a blast together, and even though none of these relationships haven’t blossomed into a long term situation, it wasn’t because of status or the arbitrary surface level stuff so many singles place importance on (I could go into more details, but out of respect for those ladies, I won’t).

So, to whatever extent you can, have an open mind. Give people a chance. Because your person may turn out to be the opposite of who you expected them to be.

Step 1: Be the Best Version of You

Only you can decide who this is or what they look like, but a lot of singles aren’t putting their best foot forward. They take an approach akin to buying jeans too small with the idea that they’ll lose weight later, when it’s actually better to lose the weight first and then buy those skinny jeans when they fit.

Since I brought up weight, let’s address the elephant in the room: there are a lot of people out there who are overweight and are going to struggle to attract others for that specific reason. They may be great human beings, but attraction cannot be negotiated, and as visual as today’s world is, I don’t need to tell anyone that appearance is paramount to success when it comes to attraction and dating (the good news is that with the right kind of diet and exercise, there’s no reason anyone needs to be overweight).

But being the best version of ourselves applies to more than our physical appearance — it applies to our financial, intellectual, and spiritual health as well. Keep in mind, by best I don’t mean perfect — I simply mean the best we can be within reason at the time.

For example, when I first became single I was significantly overweight. My initial goal was to lose 25 pounds. When I achieved that goal, I was the best version of myself — but that didn’t mean I couldn’t continue to get better. I’ve gone on to lose 40 more pounds while gaining muscle, so that my new best is better than my previous.

Step 2: Make the Time

If you don’t make the time, dating isn’t worth the effort.

Now this should seem fairly obvious, but as anyone who’s been single for more than few months can tell you, a lot of people are too busy to date. They literally do not have enough time in their lives for other people.

… and yet that doesn’t keep them from trying.

Seriously: if you don’t have enough time to date, stop wasting your time and everyone else’s. Just stop. Your time — clearly — is better spent on other things, and for those of us who are serious about this shit, it’s obnoxious.

OK, so good question: what does enough time look like?

A good benchmark is having around 6–10 free weeknights and 4 days on the weekend per month. This allows enough raw time to get to know your dates as well as options when scheduling issues arise as they invariably will.

Can’t swing that? Well again, it’s probably best to figure out how to free up more time or find an alternative arrangement or focus on other things.

Understand: if you can’t see someone at least one day a week, it’s extremely unlikely a long term, monogamous relationship is going to work. It’s just not enough time to get to know that person and sustain a relationship.

If you’re a single parent like me (50/50), this means that sometimes you’ve got to ask the grandparents or a friend or relative to watch the kiddo, or shell out the cash for a babysitter. If you’re a busy corporate-type go-getter, you might specifically schedule time for dating or even consider using paid vacation to meet people. If you’re working and going to school, then maybe you have to go on coffee dates, or save weekends for going out, etc.

Whatever the case, remember: busy is a choice. Modern life is no doubt fast paced, but there’s a lot we can do to slow things down — and if dating/having a relationship is important to you, then you have to make it a priority.

Step 3: Find an Effective Way to meet People

For me that’s MIRL — I’d rather talk to attractive women I come across in my day to day life, see if there’s a connection, and then go from there. In this, however I recognize I’m a rarity.

These days most people use some form of SOD (swipe/online dating). Personally, I think this is a terrible way to meet people for a number of reasons — even for women.

However, if it works for you, great.

The only thing I’ll say about it here is this: the dynamics, mindset, and casual nature of dating apps makes finding a long term partner extremely unlikely (Tinder is why fuckbois exist). So if you’re looking for a long term relationship/marriage, you’re probably better off finding other ways to meet people.

Whatever method you choose to meet people, the true measure of whether it’s working or not is volume: if you don’t have the option to go out with at least two people a week — not saying you actually do, but that you could — your volume is too low.

(One caveat here: if you’re communicating with more than 10 people at a time, that’s too many — ladies I’m looking at you. Remember, human beings don’t do well when they have too many choices. It’s better to have a handful of people you’re interested in than two dozen.)

Yes this means you’re dating multiple people, and no that is not unethical.

In this day and age it’s ridiculous to expect that going on one date means you’re exclusive — that’s a conversation that happens later, and when it does, then yes you need to cut ties with the other people you are seeing. But until one relationship stands out among the others and there’s some sort of commitment from both parties, it’s perfectly fine to date other people.

Step 4: Don’t Burn Bridges or Define the Relationship too Early

Once you’re officially adulting it’s unlikely you’re going to have a relationship where you fall head over heels for each other, going from date number one to boyfriend/girlfriend in the span of a week or two like what happened in high school, college, or your early twenties (if it does, then fuck yeah for you — that rocks).

As mentioned above, this likely means you’re dating more than one person. Keep in mind: they are too. Additionally, things come up, people get busy, life happens — the point is not to ask for an exclusive relationship or attempt to define the relationship until you’re fairly sure the other person is in the same boat. Because once you do either, the other person has to accept those terms or reject them, and whatever decision is made is final.

And while it’s true that attraction cannot be negotiated, it can change or build over time. It may take someone a month or two to really get to know you well enough to want to be exclusive. Maybe longer.

I’ve written before about zombies — when women who’ve dropped off the radar contact me out of the blue — but what allows that to happen is the fact our relationship was never defined, nor did I feel the need to be a jerk when things fizzled out the first time (guys, I’m looking at you — nothing is gained by expressing anger or bitterness to a woman — EVER).

A simple rule: if someone doesn’t text you back, that’s it. You can maybe contact them one more time down the line, but if you they’re not getting back to you, it’s either because they’re not interested or because something happened in their life that takes priority. Respect that, move on, and you never know: that person may pop back up when you least expect it.

Step 5: Ups & Downs are Natural: Trust the Process

There are times when everyone in the world seems interested in you as a romantic partner, and there are times when they all seem to drop off the face of the planet at the same time.

There’s not a lot we can do to change luck, circumstance, and fortune. Some people are going to get lucky and meet [special one]* right away; for others, it might take several years.

However, if you’re following steps 1–4 on a consistent basis, you give yourself an excellent chance of finding what you want in the dating world, whether that’s a long term monogamous relationship/marriage, or dating several people non-exclusively or whatever. As with life in general, if your process is good, the results may take awhile…

But they will come eventually.

Final Point: There’s a Reason You’re Single… and it’s You.

When I read articles about dating or talk to people about it, the discourse often takes shape in complaint — and I won’t claim innocence on this point, which is especially evident if you’ve read some of my earlier posts on dating.

But the truth remains there’s one reason you’re single…


It’s true for me as well.

On the most simplistic level it comes down to pickiness: we could all be in a relationship if we scaled down our standards. I’m not necessarily suggesting you do that, but if you find yourself complaining that you’re not attracted to the people you meet or match with on a consistent basis, you probably ought to reconsider what you expect or become a more attractive version of yourself or find alternate ways to meet people.

Sorry not sorry ¯\_(ツ)_/¯

I guess what I’m trying to say is that we all need to take responsibility for our situation. Remember that you have agency. The landscape of modern dating is difficult. There’s no doubt about that. But complaining about it doesn’t solve the problem, and I can guarantee no one is going to date you out of pity.

So if you find yourself asking the question: why am I single? The answer is to that question is quite simple: you. Something you are doing and or some set of conditions you have control over — whether it’s being too picky, not making time, being emotionally distant, not being the best version of yourself, or not learning from mistakes you’ve made in relationships in the past — is why you are single.

Placing the blame anywhere else is completely and utterly unproductive.

But, if you follow the steps, have a positive, open mindset, and get out there, you’ll figure it out. Just remember, there has to be a method to your madness.

That said, it’s tough out there kids. Love hurts, but it also heals… hope this helps — and good luck!


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