Shortly after graduating from college and relocating to Denver from the southeast, I was presented with a rather unique opportunity.

I was approached by a woman in her mid-thirties who asked me what my thoughts would be regarding going out on dates with random women from a wide age-range, with various cultural backgrounds, knowing very little bit about them prior to the first encounter. 

My initial response was, “What’s the catch?” followed by, “What’s in it for me?”

The woman went further to state that I’d be compensated both monetarily and intellectually. I found humor in the notion that going out with complete strangers, for money, could be intellectually rewarding.

But, I decided to give it a try. And, like so many times in my life, my assumptions about her offer were completely and utterly wrong. 

I became a male escort.

The lessons I learned were something that could have never been taught in a classroom, read in a book, nor relayed to me in any other fashion, as they could only be beneficial from being experienced first-hand.

By those who knew from day one about my “after hours” activities, or found out further down the road, I’ve been judged on countless occasions. Many have cracked jokes; some have been extremely negative and made derogatory comments, but still, I have no regrets, as the many lessons learned from my experience as a “hospitality specialist” could never be forgotten. 

Lesson #1: “Being Chivalrous, Confident and Considerate is all that matters”

On countless, women seemed awestruck when I’d show-up with something as simple as a Japanese Lily (roses are too much, early on), ask them how their day was, open the door for them, not sit until they’d been seated, or provided them with a compliment. I personally believe, and have since early on, that a woman should be complimented at least once a day … at a bare minimum. 

From my experiences interacting with what were complete strangers, I found that being confident and assertive were key, however, this shouldn’t be misinterpreted for being arrogant, nor brash. A gent should always be comfortable in his own skin and should generally be proactive, not reactive. He should never hesitate to order the type of wine (or martini) he thinks she’ll like, grab her hand and drag her to the dance floor, nor feel embarrassed to make himself look like a fool.

If there’s one thing a gentleman should never be, it’s boring. Being considerate, well, it’s key. It’s the little things that men often forget about which make the biggest differences. If the gal’s had a bad day and you have plans with your “bros”, what should you do? Change your plans. If she matters, you won’t think twice. Whether it’s a Monday night football game, happy hour, etc., there'll be other times for such things. If she thinks an outfit looks bad on her, or maybe she just got off of the scale and isn’t smiling, reiterate something about her that you truly adore.

Unfortunately, this is where I still see fellas’ falling short, day in and day out. I have friends with amazing girlfriends/fiancés/wives, and all too often, they make others a priority. How and why, I have no clue. 

Lesson #2: “Honesty, honesty, honesty … It's not that hard!”

If there’s one moral characteristic that should be held with extremely high regard, it should be honesty. This can be applied to countless aspects of life, but when it comes to dating, it's neck and neck with trustworthiness for most important trait. “Little white lies” add up, ladies and gents. 

“I’m working late, baby” shouldn’t really be “I’m cutting out early for happy hour … he/she won’t know.” 

“I’m really excited about doing XYZ …” shouldn’t be “I’m really dreading XYZ …”

If you really care about someone, tell him or her the truth. All too often, folks aren’t straightforward with each other. When this happens on a consistent basis, well, both men and women lose interest. I don’t know how many women told me they loved a handful of various things about their ex, but when I inquired about their dislikes, one thing that repeatedly came up was a lack of honesty and trust. This definitely goes both ways, as my clients were all supposed to be single, and on several occasions I was contacted by PIs (private investigators) or spouses that had been keeping a close watch on them (unbeknownst to me). 

Here’s something that should be obvious to everyone, but I can tell you, it’s apparently not. If you put a GPS (or contemplate doing so) on your significant other, well, you have trust issues. You have a problem, but they do too: they aren’t trustworthy. Either way, run for the hills!

Lesson #3: “Declining sex isn’t the end of the world.” 

Almost anyone, if not everyone, that’s ever been in a semi-serious to serious relationship has experienced this at least once: you’re rip-roaring ready to go, you want to barge through the door, rip every single piece of clothing off of the other person and let the passion commence … and, guess what, he/she just isn’t in the mood. 

Maybe they’re exhausted from a long day or week. Maybe they shouldn’t have had dessert at supper. Maybe, just maybe, they’d rather “Netflix and snuggle.” 

One thing that I think folks often times misinterpret, or simply misunderstand, is what true intimacy is. Intimacy isn’t humping her leg like a Chihuahua hopped up on Viagra, gents. Intimacy is knowing the other person forwards and backwards. Knowing what they’re going to think about something, before the subjects even been brought up. Intimacy is not a one-night stand, that’s for certain. Can a ONS be fun?  Sure. Can It be passionate? Definitely. Intimacy simply isn’t something that happens in the blink of an eye, no matter how much tequila is involved. 

Lesson #4: “Learn how to use a calendar!”

Something that was made abundantly clear to me by at least half of the clients I worked with was that way too often, men tend to forget about birthdays, anniversaries, date-nights, etc. I was actually on a date with an amazingly beautiful woman, at a nice restaurant when our server introduced themselves and asked how our Friday evening was going.

Seconds later, out of the blue, she burst into tears. 

I thought I was taken back, but the look on the server’s face is something I’ll never forget. He clearly thought we were in the midst of an argument, which was most certainly not the case. I politely asked if we could have a few moments, in hopes that it would give her time to vent about whatever it was that caused the mindset she had at the time. A few moments later, I inquired as to if there was anything I could do, and about what caused the emotional outburst. Come to find out, the restaurant printed the date on the top of the menu, and, that particular evening was what would have been her and her ex’s 6th anniversary. 

She went further to state that the year prior, she’d made reservations at the place they went for their 1st date, and had the mindset that her ex would be proposing that evening, as five years is quite a bit of time to spend with someone. Long story short, not only did he not “pop the question” that evening, but he’d completely forgotten it was their anniversary … She ended their relationship that very night.  

Just about every device that people use today has a calendar aspect of some sort, whether it’s an iPhone, iPad, or your email, so gents, NEVER forget important dates!

Lesson #5: “Learn how to cook.”

From my experiences, though most women really enjoy a nice night out on the town for a classy supper, from time to time, they’d like to see what type of skills a gentleman has in the kitchen. I went out with one gal in particular 4-5 times, each time, to a different restaurant. On our 5th date, she asked if the next time we met, it could be at my place, and if I’d cook supper. Due to certain circumstances, I declined to have her to my place, but told her I’d be more than happy to do so at hers. I spent 2-3 nights becoming the master of Martha Stewart’s cookbook … The master! 

I made a kale caesar salad to start, followed by veal saltimbocca, with angel hair pasta and asparagus. The caesar was great (but who could mess that up?!), the veal was a little overcooked (which I acknowledged though she insisted it was delicious), and the asparagus, well, it was asparagus.

When everything was said and done, I would have given it a 7, maybe a 7.5. She insisted it was a solid 9, which I knew she was just saying to be kind. Dessert, well, we skipped that for some “fun.” 

I assure you, it wasn’t the 2+ bottles of vino that led to such, it was the effort I’d put in, as she knew (we’d discussed it previously) that I was a single guy who could barely cook a ramen noodle bowl without messing it up. 

Whether it's cooking, or something as simple as a hobby that the other person enjoys (exercising, painting, a sport), going out of your way to make them know you truly want to share in things that they relish in doing, well, it means more to folks than many truly know. 

If you’re reading this, you’re probably thinking to yourself, “this is all common sense.” And, I would agree with you. Everything referenced above simply comes from the countless experiences I had with the opposite sex during my time in the “hospitality Iindustry.”  Truth be told, it was one heck of a ride!