50 Shades of Crazy! (things I learned from online dating)

December 8, 2014

Articles, Soul Seeds

After spending over two years on dating websites, you can bet I learned a few things.
Here are my thoughts, tips and a bit of advice for your viewing pleasure.
Even if this isn’t your thing, I’m willing to bet we can share a few laughs,
as I describe what window shopping for a date is really like.

50 Shades of Crazy!


I couldn’t believe how many people lied about the most obvious stuff, as if it isn’t going to be painfully obvious upon meeting that you’re completely full of sh*t. I mean, “C’mon guys… I can’t even carry a shovel that big!”

The lies of online dating profiles.

  1. For richer or poorer. Don’t claim to be a successful investment banker when you work at Taco Bell and live in a frat house with a dozen other people.
  1. Get a job! It’s all fine and well that you “used” to have a career, as we’ve all had our ups and downs, but at least be upfront about it. The right woman will understand and believe in your ability to be successful again, so give her some credit. Don’t pretend that you’re still financially independent when you’ve been unemployed for 2-5 years and are living in your parent’s basement rent free.
  1. Come again. “What’s that…? You’re a professional photographer too, you say? So, what do you shoot with?” REPLY: “A disposable Kodak (or my personal favorite) Oh, I don’t own a camera.” Better yet, is when they change their entire profile after making a connection, to include all the things you say you like in yours.
  1. Relationship status. What makes you think I’m going to be attracted to you when I find out you’re on a singles dating site, you have checked that you’re single (not separated or divorced) and yet, you forgot to take off your wedding ring before we met (hence, the lying… I know) but, don’t be such a douche! If you’re still married, go back home to your family!

Online Dating Lies


  1. I want to see pictures of YOU. Not some headless shot of your naked chest, bicep, or tattoo… Not your mother, your kids, your dog, your house, your cars, bikes or toys… Not the piles of dirt in your back yard, the piles of crap in your garage, the piles of dirty dishes in your kitchen, or the piles of dirty underwear in your bedroom. There will be plenty of time to impress me with those things IF we make it to a second date.

Profile Picture

  1. Pictures of you with your (EX)girlfriend(s). I know it makes you feel popular and cool to post pics of yourself surrounded by beautiful women, but in reality, it only makes you look like player. At least have the courtesy to use the crop function before you publish.
  1. Men portray their younger selves. OK, so maybe I can understand guys wanting to post pictures of their accomplishments more so than pictures of themselves (to an extent) but don’t make your only personal pic one that’s more than twenty years old either. I could care less if you’ve lost your hair or not, but I should at least be able to recognize you when we meet.
  1. Darth Vader. You know, most cameras and phones have an auto flash/focus built right in. Would you learn how to use them please?! It isn’t sexy or mysterious that I can only see an outline of you, because your image is blacked out. That’s just creepy. Or better yet, is when you’re completely blurry, because the pic has either been taken a mile away or is much too close (i.e. my first impression of you should NOT be staring straight up into your nose.)

Dating Profile Pictures

  1. Mysterious winks are sexy… Not! Why do ¼ to ½ of men’s profiles not even include a picture? Even more, why in the world do you bother to wink at me? Especially when I’ve stated, “no pic, no response.” Once again, this does not make you appear mysterious gentlemen. Think about it… Would you even glance at a ladies profile if it didn’t have at least one decent pic?
  1. Your height. You know, it’s going to be painfully obvious when we meet men, if I tower over you while wearing flats, that you are not a foot taller than me. There are reasons these sites allow people to choose and list preferences on their profile.
  1. Headshots only. What the heck ladies? Most men I went out with genuinely thanked me for posting recent and varied pictures of myself. One of the biggest complaints I heard was how most women only show head shots in hopes of hiding their real weight or figure. I get it ~ you want him to like you for you, but this is hardly the way to go about it.
  1. Your CURRENT weight, not your COLLEGE weight. For heaven’s sake men, it’s just as unfair for you to describe yourself as “athletic and toned,” as it is for a woman to show only head shots, when you’re sporting a 40 lb. beer gut now! Can’t we just be REAL people?

Online Dating Profiles

  1. Men over 40 have forgotten how to shave. Seriously gentlemen… at least 95% of the profiles I viewed were sporting facial hair ~ a goatee being the obvious favorite. While the rugged look can sometimes be sexy and attractive, it mostly comes across as just being lazy. Personally, I have sensitive skin and find it irritating as hell (nothing like having to worry about developing a rash while making out.) So, my most common reply to is… “Hey, I’ll shave again when you do!”
  1. First impressions matter. I’m not a shallow person, but there’s nothing that says “come hither” like a man sporting his favorite threads, which appear to have been slept in ~ a faded, holey t-shirt and basketball shorts from college that don’t even fit anymore. Look, if you seriously want to impress on the first date, show up semi-casual and ready for anything!
  1. Different strokes for different folks? Not really… Despite the cost, all 4 sites I tried seemed to be basically the same. While, as a business they may have different approaches, the types of people the online dating scene attracts, seems to be very much the same.

Online Dating


Chivalry is not dead ~ men should act like gentlemen and women should act like a ladies. Do you remember what is was like to feel all excited when you were trying to impress a girl? Well, do those things again men! And ladies, you can make it a little easier on him. Quit strutting your independence so fiercely, as to imply that he’s not needed (trust me, I made this mistake for years!) but don’t you ever take advantage of his kindness and generosity either.

Online Dating Disasters

  1. Never “Go for the gold” on the first date! Just because you bought me a dinner and a drink, that does not mean you have a right to grab my ass on the way out. Sorry gentlemen, but that’s not what you paid for!

Online Dating Etiquette

  1. Don’t be such a flake! Come on, are you really so superficial that you just suddenly quit communicating with me for no reason? If you are so distracted by the next pretty female that comes across your screen, that you decide to drop me without the slightest bit of consideration, then don’t bother coming back a couple of weeks later when you’re ‘done’ with her or realize how fake she was.

Online Dating Etiquette

  1. Write a complete sentence for Heaven’s sake! Singular verbs, adjectives, nouns, or just sending seven digits does NOT count as communication. I’m not joking; if you really want to impress someone and stand out from the crowd, why not put forth the effort to send a couple of complete sentences instead. Duh! (smiley face, wink, wink…)

Online Dating Profile

  1. Bad grammar. Seriouslee, u dont even care enuf to mak a edit wen spell chck has lit up yur antire massage lik a fire truk!
  1. Don’t copy and paste. Once again… Seriously? When I can clearly tell that you’ve held down your finger, pressed copy, held down your finger again and clicked paste, as you have in response to dozens of other girls ~ that’s just plain disrespectful and rude. I won’t reply.
  1. DicPics… REALLY? Look man, no one wants to see your junk, so keep it in your pants. If you’re asking for my # and that’s the first form of communication you send, hoping to impress, know that it does no such thing. Ever! In fact, you are automatically deleted, blocked, spammed and usually laughed at. Remember, women weren’t created to be as visual as men are anyways.

Online Dating and Sexting

  1. Men, be respectful. Men use the sites mostly for hook ups (as most often complained by women.) 

Online DatingAnd gentlemen, if you don’t want ladies after you for your money, quit using it as a lure.

  1. Women, be respectful. Women use the sites to try to secure their finances (as most often complained by men.) So, ladies, if you don’t want to be treated like a call girl, quit using the site as a potential paycheck.
  1. Grow up! Try not to take it so personally people! Not being the right fit for someone is NOT a judgment of your worth or value as a person. It just means you’re not a good match so, wish each other well and be on your way. Can’t we all just act like grown-ups please?

When “No thank you” means “Stay the hell away!”

Online Dating Honesty


Online Dating

  1. Be patient and understanding. I realize this can be an exciting adventure men, but know that as a woman, I may easily have 50-100 hits a day who are all waiting for a response. Who in the world has time for all that!? Most men however, shared they were happy just to get a couple per week. Also ladies, don’t lead him on or string him along either (honesty is always the best policy!)
  1. “Social smokers” need not apply. When I have stated in all caps “ABSOLUTELY NO SMOKERS” and you reply with, “I’m only a social smoker” what the hell does that mean? Look guys, I could care less if its cigars, marijuana, cigarettes, e-cigs or the dill weed from your grandma’s kitchen cabinet… Either you smoke or you don’t, and if you find it necessary to light up something else, besides the occasional fire under someone’s ass, than please don’t contact me. Not only am I highly allergic and can smell it a mile away, there’s nothing more disgusting than kissing an ash tray.
  1. When your greatest hobby is “social drinking.” Again, what exactly does that mean? For me, it means I might enjoy a couple of drinks a month. Apparently in beer country though (Colorado, known for its healthy living and active lifestyles) it means to stop by the pub every single night after work and have several beers or glasses of wine. Around here, you’re not considered a drunk if those are your habits ~ somehow, you’re a socially acceptable beer snob instead.


You will learn more about the persona of your potential partner by spending 30 seconds in their presence than you will from emailing them for six months. So, if you find someone you’re interested in, I suggest meeting face-to-face as soon as possible.

When to Meet - Online Dating

  1. Call me old fashion, but there’s nothing like real human interaction. You can email, text or even talk on the phone for hours, but the truth of the matter is people can pretend to be whoever they want while hiding behind their devices. I learned the hard way that 9 out of 10 times, had we just met first, there would not have been a second phone call even.

Meeting Your Online Date

  1. The more the merrier? Not exactly. Being on more sites and going on more dates does not make your odds of finding the love of your life any better. In fact, it only complicates things. I thought the more exposure I had, the better chance of finding my husband, but I don’t think that’s necessarily the case now. It just meant my inbox was on overdrive 24/7! I don’t need a hundred different men… I’m only looking for one.

Finding your soul mate online

  1. Learn to be picky. It’s OK to have high expectations and standards for yourself ~ In fact, you should! I learned that one of the reasons I’ve mostly been a “yes” girl is because I’m afraid to miss out on anything good. But, there are way too many online predators and people who are seeking others with a good heart, so they can take advantage of them. Learn to just say, “No.”

Dating Profiles

  1. Have fun! Look, I’ve hated dating as an adult. Although, I believe it’s supposed to be fun with the right person. Learn to adopt a positive attitude though, no matter how you feel, and to be optimistic. The other person is probably just as nervous or even fed up as you are, lol ~ you might as well learn to enjoy the process and help make it less painful for you both!

I hat online dating!

  1. But, but, BUT… Men will still say absolutely anything to get a woman into bed, no matter how old they are! When you’re 20 something it’s “I love you” and “I’ll call.” At 30 something they become very complimentary, and instead of “I’ll call,” they reassure you that they want the same things as you do (marriage, kids, long-term relationship, etc.) At 40 something they don’t even bother with the sweet talk anymore. By 50 something though, many seem to come back around… they have sewn their wild oats, learned what it means to be romantic, discovered the benefits of slowing down, and embrace simple honesty. So, now you can finally get somewhere which may resemble a serious relationship… most of the time, lol! 

  1. Be specific. Unless you’re just looking to get laid that is. I learned how to make my profile as specific as possible to fit what I was searching for. However, they recommend NOT doing this as a way to increase your chances of receiving more matches, but why would I want more matches that don’t fit my criteria? So, I did the exact opposite and found it very beneficial, such as “seeking a man who will pray with me,” and  “no children under a certain age” and “absolutely no smoking.” It helped take care of certain types right off the bat (well, most of the time that is!)

Online Dating Honesty

  1. First dates can be super awkward, but I came to find out that those who suggested some sort of lavish activity for our first meet usually did so because they were afraid of having to engage in conversation. Interestingly enough ~ I found they had good reason to be. I learned to avoid these invites for our first meet and greet.


Unfortunately, society seems to be forcing all of us to have to protect ourselves more and more with each passing decade, so both parties need to use some common sense and just be careful.

  1. Always meet in a public place. Look, you don’t know this person ~ If they’re crazy, insane, an ex-convict, or better yet… if they currently have a warrant out for their arrest. Be smart and play it safe, best to do that during the daylight hours, tell a friend or family member where you’re going, and (ladies especially) don’t give out your home address!
  1. The first meeting is NOT a date and should be non-committal, like coffee or cocktails. Now, I know a cup of coffee doesn’t seem that romantic, nor does it allow much time for intimate conversation. But, neither is it romantic when you realize that you’re strapped into a 2 hour dinner date with someone who has mannerisms and idiosyncrasies that you can’t stand, or who is so busy talking about himself that he doesn’t even notice when you leave the table. Keep your options open for the first meet and if things go well, you can always choose to extend it.

Online Dating

  1. Quit making promises! I can’t tell you how many guys tried to snag me into meeting or coming over by offering to “do” things or “help” me with something. I’m guilty of trying to accept a couple of offers (after much communication and trying to develop a friendship) only to never see them again afterwards. Because, rather than doing what we agreed upon when I got to their home, I would (without fail) be given a tour of the house first, where they then seemed to get stuck on trying to impress me with their master bedroom instead.  Do you know that deer in the headlights look? That’s the same blank (oh sh*t, what do I do now) look I’d get when I wouldn’t take the bait, as they scrambled for creative reason or excuses to get me to step over the threshold of their palace. Nothing makes the notches on your posts more apparent gentlemen.

Online Dating Tactics

  1. Ladies, get his info. first. Now, I understand some men may not like this or think it’s a double standard and for those of you who do, it’s OK, as I’ve learned the hard way that you’re not going to be someone I want to meet anyways. Unfortunately, a woman does have to protect herself even more in today’s society ~ For the most part men, you are going to outweigh her in almost every area so a smart, single woman should never blindly trust without some verification.
  1. Don’t be the ‘tell all’ type. I might warn you to stay clear of anyone who expects you to divulge every little secret the first time you meet, and this comes from a woman who wears her heart on her sleeve. If a man insists on immediately knowing too many personal and intimate details about your life, it means one of two things: He either wants to run a background check (although, probably not) or he has a controlling, manipulative and abusive personality in which, he’s screening for vulnerabilities in search of his next victim (I’ll elaborate more on this in my next post.)


After all, why else did you join this site? Maybe even say yes, where you might otherwise say no, especially if you’re basing most of your opinion on looks (well, once again, unless you’re just trying to get laid.)

  1. Please don’t be intimidated men. I can’t tell you how many emails I received from men who said they found my profile to be intimidating (I’ll include it in my next post for you to see as well.) While I surely didn’t mean to come across that way and would receive plenty of advice on how to tone it down (you know, so I wouldn’t appear as giving, successful, smart, or articulate) I never did. I figured the type of man I’m seeking won’t be intimidated at all, but will feel the opposite and thrive off my qualities, seeing them as assets, just as much as I will his. That being said, those men who were respectful and took the risk in contacting me, regardless of how they were feeling, got a response and most often a date from me ~ if for no other reason than they had the balls to make a move.

Singles Dating Online

  1. If you’re serious about meeting me, then read my profile! It was painfully obvious when someone would contact me who clearly did nothing more than just glance at my pics (sadly, this was the case more often than not.) This only proves how superficial and shallow you are. 
  1. Ladies, be willing to take a chance where you might otherwise not. You may be pleasantly surprised! As a woman, I never base things upon first appearances, because I know with time that if I fall in love with the person, I’ll also fall in love with their looks. However, I can appreciate that men were created differently and to be much more visual (that isn’t an excuse to be shallow though either guys.)

Expectations of Online Dating


You can bet I will be writing about some of these experiences in my book.

  1. I acquired a stalker on eHarmony.com who has the gull to remind me of when our yearly anniversary is.

Online Stalkers

  1. I actually married a weasel scam artist and sociopath from ChristianMingle.com, only to find myself fleeing from another very abusive relationship (in all ways) and filing for divorce just a couple of months later. *California incident

Dating Sociopaths Online

  1. I met one of the most intelligent, cunning, and dangerous psychopaths/sociopaths on eHarmony.com who stripped me of practically everything I had (a man who was later convicted, stripped of his leadership, and imprisoned ~ touché.) *Hawaii incident

Dating Sociopaths and Pyschopaths

  1. I had a love/hate experience with Match.com ~ Surprisingly, this seemed to be the biggest ‘hook up’ site of them all (just an upscale/glorified version of Zoosk really) where uniformed officers from every branch seemed to pass the bucket and play tag team in this town.

Match.com Online Dating

  1. My briefest online affair was with Zoosk.com where I definitely had the most crap to sort through.


The flip side of the coin and I wish there was more to put in this section…

  1. Unexpected opportunities. I unknowingly met one of my greatest online supporters through eHarmony.
  1. Lifelong Friends. I encourage you to keep shoveling through the barrage of sh*tJust like in everyday life you’re searching for that needle in a haystack, but don’t lose hope, because it’s in there! (Regardless of where you end up finding it.) I met the most respectful man I know off one of these sites, whom I’m honored to consider a trusted friend.
  1. Don’t lose hope even if you are still single after all is said and done, because I still am! When I think about it though, I don’t want to meet someone who spends his all days and nights surfing these different sites anyways.

Soul Seeds…

Online dating is a unique adventure within itself. If you plan to travel down this path, be prepared to go on a journey of self discovery as much as anything else. Be honest, be smart and trust your instincts. Most of all, try to have fun with it! At the very least, know there will be lessons learned just like with anything else, so view it as an opportunity if nothing else, because you never know who you might meet. I am especially grateful that this experience helped me to create better personal boundaries and set higher standards and expectations for myself. I wanted to give it an honest try, because I do know people who found success this way. It’s not for me though and I knew that before signing up, but I am just as much of an optimist, as I am a realist.

Obviously, this is written from a female’s point of view too, but I tried to include things the guys shared with me as well. I would like to say that for every 10 jerks I met there was at least 1 good guy, but I’m afraid the ratio proved to be more like 1 in 50. I did meet one man in particular however, who for me, set the standards and really showed me how a lady should be treated. So, that alone was worth it! And yes, for the first time in many years, I am definitely smitten by him, but only time will tell. If nothing more develops between us however, then all of my window shopping on these sites was worth it just to find a genuine lifelong friend and example of how I deserve to be treated.

Marilyn Monroe

*Stay tuned for future articles, where I will share my online dating profile
and elaborate on some of these fifty shades.


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27 Comments on “50 Shades of Crazy! (things I learned from online dating)”

  1. moxieluster Says:

    Loved reading this haha! Most of it is so true, and you know so many people get “Catfished” because people are not honest on their profiles.


  2. struthi giridhar Says:

    That’s a looott of tips. getting it framed. ;)


  3. Harbans Says:

    Just incredible. Informative.


  4. Carol Balawyder Says:

    This is a fabulous post. I especially like I Told her I was a Pitbull! :)


  5. Jessie Jeanine Says:

    Oh my goodness… Some of your guy’s comments crack me up!

    No Anthony, not too much info my friend, lol! Then again… who’s to say? I tried giving the responsibility of finding my next date to my daughter and her friends, but they didn’t bite :) As for the lying and pretending ~ yes, that makes it almost impossible and is why it stinks! It really takes all the fun out of it when you have to play detective all the time instead of just being able to relax and have fun.


  6. Andrew Petcher Says:

    I thought WordPress was an on line dating site when I joined!


  7. brodyruach Says:

    Oh Jessie, good points but you’ve missed the most important way to endear yourself to a man.

    Putting out. On the first date. Is a must!

    Just kidding… or am I? I am.

    I’ve just started reading your stuff but so far it’s cool.


  8. Gretiana Says:

    That was a good one Jessie. I did laugh a lot but I learned some stuff too.


  9. Jackie Saulmon Ramirez Says:

    My daughter took a photograph of a meat counter with hams hanging in it for her profile. She felt disgusted as if she was selling herself. She was very picky and did eventually find her perfect match.


  10. theoldfellowgoesrunning Says:

    Jessie, when I saw “4,041 more words”, a lot of times with different writers, I will just move to the next article. I’ve always had a lot of respect for you and your writings, so of course I’m going to read. :)

    Must tell you, this really was an eye opener (#21….I am shocked), and I am really fortunate the Lord has given me the precious wife I cherish, now 26 years married. I shudder of the thought of ever having to date again.

    So Jessie, I commend you, this has been quite the journey these past 2 years using dating websites. Love your standards (#33…seeking a man who will pray with me) Your advice and safety was excellent.

    I think of my own 2 daughters, and as a dad, pray they will be safe and not get hurt when the time comes to search for life partners.

    And Jessie, may the Lord bring a man your way, that would treat you with the love, honour, care and respect you so deserve.




    • Jessie Jeanine Says:

      Hi Carl and thanks for hanging in there, lol! This was just going to be a “quickie” if you will only listing the bullet points, but I can get so caught up in the details and explaining… you should see the other 3 pages I still have, lol! I’ll be making those into articles next and didn’t realize how much there was to tell after that long until I started writing. I’m sure it could probably be another book even :)

      Anyways, thank you so much for your encouragement and support as always. Give your beautiful wife a hug from me as well and I admire your 26 years ~ that’s absolutely incredible! Love and cherish each other always… even when you disagree (although, it’s apparent you both already know how to do that, lol!) Speaking of our daughters… I never really knew what it was to pray until I became a mom, and now especially as she’s entered young adulthood herself. On the lighter side though, you may get a kick out of “Application To Date My Daughter” if you haven’t seen it yet ~ I kid you not Carl, I gave this to a couple of young men she brought home ;)

      Many blessings my friend, to you and your family always, and be well!


      • theoldfellowgoesrunning Says:

        Thank Jessie for the application link. It was brilliant, funny, and I can see how some young men should be handed a copy!.
        Thank you for this! :)
        P.S. When my wife wakes up, I’ll pass on that hug, and what you shared. THANK YOU! :D


  11. tonyasmithauthor Says:

    Dating sites are why GOD invented pets Jessie! Just kidding…


  12. Madiha Hussain Says:

    lol, great post :) check out my blog please if you have time, thank youuu


  13. osarobohenry Says:

    Awesome post my friend. God’s blessings to you :)


  14. Jueseppi B. Says:

    Reblogged this on MrMilitantNegro™.


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