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Sex Talks #5 - The Single Male Guide to Dating

The Single Male Guide to Dating

Not too long ago, I wrote a series of stories on my Instagram page giving my thoughts and recommendations on what single men should do to date more effectively in the modern era. The impetus for writing this rapid-fire storm of stories came after having a discussion with some friends. We talked about a mutual acquaintance who was devastated after consistently having a female he knows back out of events he’d plan with her. Unfortunately, this was a common occurrence. For the past few years, I’d often hear from male friends and from other men online the same or similar scenarios. I've also experienced the same situations on multiple occasions. However, over time, I decided to treat dating as more of an experiment and invest less time into the specific outcome. In doing this, I’ve noticed some consistencies as a result. Personally, my philosophies on dating and relationships have changed dramatically over the years and I think modern day men and women should adapt to the times. After posting the stories to my social media pages, I received quite a bit of positive feedback and many people suggested I make this into a more full-length article. So, with that being said, what you’ll read in this article is a result of the feedback and suggestions. All of the suggestions I provide came from personal experience and are tactics I personally use. As a brief background, prior to college I’d never been on a single date or had even kissed a girl. I went to an all-boys school in high school and basically spent 0 time with women up until college. As a result, I have absolutely NO GAME in college and I’m sure every girl I interacted with would pick up on it. I’ll save some of the embarrassing and awkward stories for future articles but, over time, I realized that getting better with the opposite sex was something I had to get good at. One of my philosophies is that a lot of problems men have in life spawn from an inability to interact effectively with women. I wanted to solve this problem while it was minor. Plus, at the time, the goal was to be in a relationship. However, over the course of several years of trying to find a girlfriend, I made a ton of mistakes. The following list will go into detail on the several mistakes I’d consistently make and how I adapt to them. As a side note, I do not claim to be a dating coach, expert, PUA, or anything like that. These are all my personal beliefs and should be implemented and adapted to fit your lifestyle, personality, and objectives. I call this the Single Male Guide to Dating because I believe that dating as a single male versus a male in a relationship or a female has distinctly different rules. This article is designed to be a heads up of what to expect in general in order to minimize unfavorable outcomes.

Lesson 1: Don’t Take Rejection Personally-It often Has Little to Directly Do With You

This is a hard rule for men to grasp. I think this is a difficult rule for any human to grasp. However, understand that rejection is usually not personal. If you meet a female you’re interested in and she doesn’t accept your advances or turns you down, understand that it doesn’t necessarily have much to do with you. It could have everything to do with the circumstances. I once met a girl at a bar who I almost instantly hit it off with. We vibed and had a lot of fun during our brief time together. While hanging out, we discussed going out on a date to learn more about each other and she seemed extremely the time. However, as the night went on, she drank a bit too much to the point where she couldn’t walk straight. My primary concern, especially when I’m with females, is to ensure their safety. This goes double when you’re out at a bar and there’s the risk of cops detaining her for being too intoxicated. Also, as a disclaimer, I don’t really encourage any guy to try and sleep with drunk females--especially girls that are incapable of basic motor skills. With that being said, I offered to order her a lyft and have it take her home. Besides her getting slightly too drunk, I didn’t think the night went poorly by any means. She was fun and we clicked a lot. A few days later, I followed up to ask if she was still interested in going on a date. It took a few days for her to respond which caught me off guard slightly because, like I said, I truly thought we had a good vibe. Eventually, I followed up with her and she responded. She explained in great detail that she didn’t want me to think negatively about her and that she never gets that drunk. She further explained that she felt embarrassed by how much she stumbled and how drunk she got. Rejection at its finest. Now, while someone might believe she was making an excuse not to meet up, which is a possibility, I genuinely believe she considered the initial interaction to have gone poorly and, for that reason, opted out of a date. Perhaps she thought I’d judge her or have a negative interpretation of her. It’s difficult to say exactly. However, the point I’d like to make is that she didn’t technically reject me, she rejected the idea of a date due to some circumstances. I tend to find that guys interpret the world from a more objective, straightforward, and linear perspective. In a scenario like that, it’d be easy to ask: What’d I do wrong? Why wouldn’t she like me?

Personally, I’d say the answer is: nothing is wrong with you. The timing was bad or the circumstances weren’t favorable. Understand that you can’t truly be rejected unless the person knows a significant amount of information about you. If you ask a girl out, she’s known you for a few years and has interacted with you on a multitude of occasions, and she still rejects you, she’s probably rejecting you.

If you ask a girl out and she’s known you for all of 10 minutes and your interactions were stifled by the sound of loud bar music in the background, she’s rejecting the projection of you she’s gathered in a brief span of time. Or, more likely, she’s rejecting the situation. This might be a tough concept to keep in mind and it took me a while to understand but it’s worth knowing the next time you get rejected. Don’t take it personally. Lesson 2: Always Talk to Multiple Girls if you’re Single

This is probably a weird one but trust me when I tell you, this rule alone will make dating significantly simpler. Of course, I must add: this guide is for single men. If you’re not single and you’re in a relationship with another person, you should be focusing solely on that person (unless you and your partner have consented to do otherwise). I do not condone men that have a partner and actively cheat.

With that being said, if you’re not in an active relationship, I highly encourage you to always have multiple options. Let me explain why. When I was in college, there was a girl I was absurdly attracted to. Let’s call her Kathy. At the time, Kathy checked all of the boxes for me. She was cute, fun to be around, liked video games, and had a hipster-ish style that I found super attractive. Those were the extent of my standards in college. I was obnoxiously needy in college and always would ask her to “hang out” or “come over”. Granted, many times she did, but our interactions never escalated beyond simply being friends. I’d try to date Kathy for years with no luck. In fact, I’d pass up girls that were interested in me solely because I was so into Kathy, I was fixated on the idea of dating only her. Eventually, she graduated. And I asked myself exactly why she was never truly interested. She didn’t have a boyfriend and there always seemed to be a connection (at least that’s what I thought at the time). After a lot of contemplation and seeing how some of my other friends would interact with girls before, during, and after dates, it suddenly hit me. I was far too available. I’d always reach out and hang out with the underlying goal of dating her. I’d look at my friends that had far more success than me and I noticed a BIG difference between them and myself. They didn’t particularly care if they got the girl or not. And one girl didn’t particularly matter to them too much. I’d watch my friends go out to the bars and see their interactions.

They’d jokingly hit on several girls back to back. If they were rejected, they were unphased. I actually had a friend in college that was so bold that he once hit on 3 girls in a group back to back. Literally, he’d ask the first girl for her number. She’d say no. He’d then laugh it off and ask the second girl. She’d say no. He’d then turn to the third girl and ask the same thing. She’d laugh and say, “sure”. Next thing you know, they’d be making out. Keep in mind, all 3 of these girls were literally friends that worked together and they were all about a foot away from each other. Also, he literally asked them within seconds of each other.

I bring this up because I realized a key was to basically keep your options open. None of my friends that were great with girls were desperate. They always had other girls that they were actively talking to or, at the very least, had the capability to just talk to another girl. They weren’t outcome independent and, as a result, they didn’t give any particular girl an abundance of attention. This was the exact opposite of what I did with Kathy.

But why is this such a good rule for guys? Well, I’ve been in situations where I’d overly invest in girls. I’d set up a date and cancel plans with the hope that she’d show up. If she didn’t show up (and as I’ll get into later, most girls will reschedule or not show up) my day was ruined. However, once I started talking to multiple girls at once, this no longer became an issue. Sure, girls would still flake but it didn’t matter because I’d be able to still hang out with a different girl either the same day or at any convenient time. Also, talking to multiple girls gives you leverage to not be clingy. I’ve personally found that girls are immensely turned off by guys that come off as excessively clingy or needy. This section in itself can go very deep but I’ll keep this surface level. Always have other options in mind.

Now, I’ve mentioned this to females I know in order to see their thoughts. Almost all of them would question this logic and say that it’s terrible. I disagree. In fact, I typically argue that women do the same thing by default, just in a different way. However, since men tend to be the pursuers of women and women tend to have the luxury of taking a more passive approach to dating and relationships, it plays out slightly differently. Here’s what I mean: Women have multiple options because there are ALWAYS many guys approaching or interested in them whether that’s in person or online. This is true even if the girl isn’t actively aware that other men are interested in her. This is why I have the rule that guys should have multiple options at all times. Effectively, you’re doing exactly what she’s doing. However, you have to actually put in work to talk to multiple girls and risk rejection. Women, typically, don’t have these same risks. Trust me, even if you think a girl is a great match, keep your options open until you’re exclusively dating. Otherwise, you will have some emotional burdens because of the following rule.

Lesson 3: She Will Flake

Out of every date I’ve ever tried to organize or arrange, I’d estimate that I’ve been flaked on for about 75-90% of those dates. I've come to discover that in general, women (at least in their 20s) aren’t great at committing to any particular situation or event. I and other men I know have paid for an event (sometimes expensive events) only to have the girl reschedule several minutes before the meeting time or, oftentimes, just not show up at all with no warning or follow up. I’m not exaggerating when I say that I’ve been flaked on so many times that I can almost always predict when a girl will or won’t show up. My counter to this: make multiple plans. That’s really it. Don’t go into any situation in which you’ve invited a girl with the mindset that she’ll show up. On the contrary, assume she won’t show up at all. If she comes late (which is also a common occurrence) then consider that a plus. If she shows up on time, you might as well consider the date successful. To a degree, I’m writing this tongue in cheek, but the core message stands. Anticipate her not coming to any date you’ve set up. My next rule will have another strategy you should implement but typically, I set up dates with a backup plan in which I can either be productive or hang out with friends. Very often, I’ll tell a friend, “Hey, I have a date at 7pm but just in case she doesn’t show up, are you down to do A,B, and C at 7pm”? More often than not, I’ve found that males tend to have relatively open schedules until they’re invited to do something so you’ll almost always be able to salvage a flakey date with an equally fun or far more fun time with your male friends. Again, this will sound terrible when reading this, but as a male, you need to keep your time and emotional well-being intact and at the forefront of your concern.

Personally, one of the most important resources we all have at our disposal is time and it’s extremely disrespectful in my opinion when someone disregards your time as if it doesn’t matter. I can’t tell you how many times I’ve emotionally invested on a date just for the girl to not show up at all. Also, be prepared to have a girl text you minutes before the date and say that something came up and she’ll be unable to make it. I think there are some circumstances in which a cancellation or last minute reschedule is perfectly acceptable. However, with girls in particular, I’ve found it to be so consistent and predictable that it tends to come off as a massive devaluation of your time. You’re free to follow up with her as you see fit, but personally, when a girl flakes or reschedules at the last minute, I almost always discontinue contact with them or I ONLY do so when she's willing to do 95% of the follow up work.

Why do girls flake? I can’t give you a specific answer that is objective but I have a theory. My theory is that due to social media and the opportunity to find fun events on the internet easily, most women (at least in their 20s) have an abundance of opportunities for events that seem appealing. I sense that they simply plan throughout the day which event seems most appealing to them and wait until the very last second to truly decide which one to go to. Essentially, I believe girls weigh their odds, albeit at your expensive oftentimes. In lesson 5, I’ll discuss a strategy that I believe minimizes flaking but I want to set this next lesson as a prerequisite of sorts to understand. Lesson 4: Always Make the First Date Low-Investment

My belief: dating is a very expensive hobby. It’s expensive from a time-perspective, an opportunity-cost perspective, and from a financial perspective. Interestingly enough, I tend to find that many females I talk to don’t particularly like going on dates. I’m not sure what the exact reason is (as no girl has given me a direct answer as to why they don’t like dates) but I sense it’s due to a date having a high degree of uncertainty. I believe that since a date can be either fun or awful with no true way to predict the outcome, most girls wouldn’t prefer them over an event like a concert that may have a high-certainty when it comes to excitement. I can’t confirm this but this is just another theory. I’ve talked to a lot of female friends and I’m always stunned when they bring up their cons to dating. Personally, I feel like for men, the ratio of pros to cons are unfavorable while the pros to cons ratio is very favorable to women. On the other hand, most women I’ve talked to seem to have a common fear of being hurt or sexually assaulted on a date which I find to be a very unrealistic fear. While I don’t doubt the possibility of it occurring, I find it unlikely that a female will get sexually assaulted at a crowded Starbucks on a Saturday afternoon at 2pm.

Regardless, my belief is that due to the misweighted pro-to-con ratio as a male, the most strategic thing to do is to make the first date a very low investment one. In college, I’d take girls out on dinner dates or try to plan out an eventful first date with several venues to leave a lasting impression and, as I can recall, there was only one situation in which the date went favorably enough to warrant a second date. I’ve found that a simple coffee date works perfectly. It works perfectly for a few reasons:

  • It can be done in a public setting so she can feel safe about meeting a stranger or someone that she’s had few interactions with (if you met her at a bar or while just walking around)

  • It’s not expensive. As I’ve mentioned, if you’re talking to multiple girls and going on multiple dates a month or week, your dates WILL add up. An average dinner or bar date can cost $20--and I’d say that I’m being extremely generous considering a single drink at a bar depending on where you live could cost you $12 alone. Once you take 2 or more girls out...well, you do the math.

  • You can actually talk to the girl and learn about each other. I’ve made the mistake on a few occasions in which I’ve gone on movie dates, bowling dates, bars, plays, etc. and the major issue is that you’re effectively spending 30 minutes to an hour or more without talking. If you try to force it, it’ll get awkward since the setting doesn’t usually call for a lot of talking. But, on the other hand, if you don’t talk, it’s also awkward since neither of you really know each other.

  • Both of you have an excuse to leave. Sometimes, you’ll go on a date and the vibe just won’t be there or you won’t connect. That’s fine. I’ve gone on dates and could sense that the girl wasn’t enjoying herself and wanted to leave but felt like she was obligated to stick around. I’ve also been on dates where I wanted to leave but felt like I should stick around. This usually occurs during a dinner date in which you are at the mercy of the speed of the waiter/waitress. A coffee date can last as long as it takes someone to finish their cup of coffee.

I have some female friends that have asked, “Well what if she ONLY goes on dinner dates for the first date”? My personal suggestion: she’s not date-worthy. Let someone else take her on that first dinner date. Don’t let it be you. Perhaps that sounds mean, but I’ve found that if the girl is generally interested, coffee will suffice. Usually, if the girl is very strict about going on specific types of dates initially, it’s a sign of her personality and it’s not typically something that will improve. This tends to be a sign that she has very high (and likely unjustified) expectations. Now, with all of this being said, I do think if you have the funds to do so, my following lesson is worth attempting (depending on how into the girl you are and what your overall goals are).

Lesson 5: Fun Dates are Best

This might seem strange to write out. You might be thinking, well OF COURSE a fun date is best. Why would anyone go on a boring date? But I write this because I believe that a date that allows you to talk and do something unusual is far superior to coffee. However, as I mentioned, I only recommend this if you have disposable funds, if it’s a second date, or if you really like the girl and you’re not stuck on the outcome. It’s important to keep in mind that fun is subjective and it’s probably a good idea to do what might be fun in her eyes, not necessarily just yours.

A lot of guys will make money because they think money will attract women. I don’t think this is true. I have plenty of friends that make well over 6-figures and their dating life didn’t suddenly improve as they made more money. On the other hand, I think we all know men that have low-income jobs, no job at all, or don’t telegraph how much money they have and they do just fine with women. I see money as a tool for high-quality and fun dates. For example, a cool first date could be Axe-throwing or Go-Karting. While it is more expensive than coffee, it’s higher energy and still offers time to converse. Overall, don’t be boring! I think girls like fun and excitement and I see a lot of men that like to go hiking or on relatively low-energy and low-excitement dates. I think if the girl likes you enough, she’ll go on this kind of date.

However, if she’s lukewarm about a guy, I don’t think something like that will be effective. You’re much better off bringing up an exciting date for a lukewarm girl than something plain or easily done. Like I mentioned, I’d be careful about these kinds of dates and use them sparingly, but if you can afford to go on an exciting date with the anticipation that the girl you invite will likely flake or not respond afterward, I would attempt dates like this. If nothing else, you will enjoy yourself, which I think should be a primary objective of a date anyway.

Lesson 6: Qualify Girls. It’s a Process of Elimination.

Far too many men allow girls to have poor character. I’m not sure where this began but I tend to see most interactions as women disqualifying men. I think it should be the other way around. I believe you, as a guy, should vet girls for their own character and disqualify them if they don’t seem to be a good fit. Of course, how much you vet a girl will obviously depend on your objective. Obviously, I understand that for many men, the sole objective is sex and not necessarily a relationship. Even if that’s the case, vet accordingly.

I’ve already provided a few ways to disqualify girls. If she’s flaky, disqualify her. If she has unreasonably high expectations, disqualify her. If she’s too narcissistic or vain, disqualify her. I think if you’re single, you’re better off disqualifying more girls.

For one, in a weird way I think it makes girls slightly more interested in you. I’m not suggesting you should disqualify girls for this reason and try to be negatively manipulative, but I do think it’s a bit of a confidence boost to see a girl reach out to you instead of you constantly chasing after her. Two, I say this not to seem rude or mean, but over the years of dating, I’ve found that many women you try to date will waste your time. I’ve seen so many men get strung along for months or years (including myself) by a girl that gives them enough positive attention to make them think they’ll accomplish their goal. It’s as if she’s dangling a carrot that’s always just a fingertips length away. Meanwhile, the guys are wasting opportunities in the process. As I suggested earlier, this literally happened with me and Kathy. I know it wasn’t intentional on her part, but in hindsight, I should have been looking for more reasons to disqualify her ( although not in a mean way, mind you). If I had done so, I may have been in a far better position to date some of the girls that I passed over that were actually interested in me. What’s a good way to disqualify girls? Simply know what you’re looking for and rank deal-breakers and exceptions. Oddly enough, a lot of guys I talk to don’t really have deal-breakers. I think most guys have a mindset that something is better than nothing. I don’t particularly believe in just settling for whatever and I think there should be some boundaries. What’s your minimum and maximum height? What’s your minimum and maximum weight? Is there a body size you prefer? Do you mind if she curses a lot?

Do you prefer her to be high-energy or low-energy? Do you like tattoos on girls? Do you like dyed hair on a girl? Do you care about how busy she is/her career choice? I feel like just answering these questions gives you an idea of who to qualify and disqualify. For example, I don’t particularly like girls that smoke cigarettes. I also don’t particularly like girls that are over 5’8. I don’t think there’s anything wrong with having preferences or standards. Having standards helps you zone in on what you want.

Lesson 7: Don’t be indecisive

There’s something about indecisive men that bothers me. There’s something about indecisive people in general that annoys me but men that are indecisive strikes me at my core. Perhaps it negatively reminds me of a previous version of myself...or maybe I just see the impracticality of not knowing where you want to end up in life. Or maybe there’s a time-wasting component of it that repulses me. I can’t say for sure, but I absolutely dislike it. If you plan on going out on dates (or just living an interesting life in general) I think it’s absolutely necessary to have some idea of what you want. Something I’ve noticed about women (and I’ve talked to female friends about this, which they’ve verified to be true) is that they don’t particularly like making decisions and would much rather someone else make a decision for them. Granted, I think this is true for a lot of people as making decisions is typically not fun and requires planning and a degree of mental effort as well as organization, but I think as the man, you should just decide. This reminds me of the common scenario of the man asking, “what do you want to eat”? It’s so vague and open-ended. There are too many options. In sales and marketing psychology, you learn that humans freeze up when confronted with too many decisions and have a hard time deciding on any. Again, I’ve stated this earlier but I genuinely think girls like fun and they like to act on the most appealing option available to them. Nothing is more unappealing than having to choose between a variety of less than ideal scenarios.

If someone came up to me and said, “Lenny, what do you want to do today”? I wouldn’t really know how to answer that.

“Ideally, I’d be on a boat in Miami with perfect weather while partying with 50 insanely hot female Instagram models and only 4 of my closest male friends while making 1 million dollars an hour. If you can’t make that happen right now, why are you asking”? Obviously, I’m exaggerating but do you see how that vagueness opens up an absurd answer. My personal recommendation: Have a date idea in mind and invite her to it. If you truly can’t decide between one idea, offer two and let her pick which one seems better. These are 7 lessons I’ve learned over the years of dating while being single. I hope this helped in some way. If it did, please do me a huge favor and share this with someone that might find value in it. It would mean a lot to me. Also, please comment and let me know what you think about this or DM me on IG or Facebook. Feel free to ask any questions as well.

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