5 Fun Ways To Date For the Highly Imaginative And Unapologetically Cynical


1. Always ask, what’s in it for me?

If a guy or girl wants to go on a date with you, what is the incentive? Are they going to be fun? Are they going to put out? Or, are they going to be a giant fun suck that you have to get dressed up and go out in the cold for when you could be on the couch with Netflix? Don’t date to be nice, or because it’s difficult to let someone down.

Way too many people assume going on a date is better than not going on a date. WAY too many people assume that having a boyfriend is better than not having a boyfriend. But, you know what they say about assumptions. If a person can’t provide an actual reason why you’d go out of your way and put work into a relationship, they probably aren’t very smart or self-aware, and you can live without them.

The fun part, and the power shift, happens when you force people to identify what value they bring to your life. You’ll be surprised at how much harder people work when you frame your expectations in these terms.

2. Date an attached person

There are people who’ve met the “best friend” type person they want to marry, grow old with and raise children with. However, just because they’ve found a great partner, doesn’t mean they are getting everything they need in terms of excitement, passion, and sex. It seems pretty far fetched to assume you’d find all of this in one person. For realists, an affair can be a sexy, fun, exciting short term adventure. As another Thought Catalog article recently argued,

I’m not arguing that we should be happy and content with a loving husband even if he does have 4 other wives; no, what I’m arguing is that men have the capacity to love—sometimes more so than women—and we shouldn’t dismiss it as bogus just because it doesn’t resemble our approach to love.

Peter Altenberg was a German intellectual from Vienna who lived during and partook heavily in Vienna’s café life. One time a young lover of his complained, through tears, that he only liked her because of the sexual satisfaction she provided. To which Altenberg replied, “Was ist so nur?” or “What’s so only?”

3. Consider a lucrative first marriage

Did you know that you can get money just for getting divorced from someone who made more money than you? Seems insane but it’s extremely common, you don’t even have to have kids. The divorce rate being what it is, chances are you’re already destined for multiple marriages. Why not hedge your bets?

4. Leverage dates for free stuff

An important exception to the first rule, is when a date is a fun experience you wouldn’t otherwise get to enjoy. For instance, does someone want to take you to see a baseball game from their company’s dugout seats? Try a kind of food you wouldn’t experience otherwise? Do an adventurous date like paddle boarding?

Always say yes to these kinds of dates because it’s a fun life experience, and you want to accrue as many as these as possible.

You also shouldn’t feel bad about this if you aren’t SUPER interested in the person because snap judgements can be wrong. They are getting the opportunity to plead their case as well as the chance to do something fun they wouldn’t want to do alone.

5. Do it for the memoir

People who have exciting lives can write great memoir’s and make a lot of money.

People who get married and have babies and do all the things that look great on Facebook don’t really have an interesting angle to sell a publisher on.

Keep this in mind. Should you go out with someone 20 years your senior? Sure, seems like an especially juicy chapter.