10 Reasons Dating Sucks. ~ B. McClaskey


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After reading the title, I bet you are thinking one of two things: “This woman is a bitter rage-bag who needs some major help” or “Sigh, I know right?!”

Maybe you are the type of person who enjoys dating. You like the thrill of the chase and you own a black American Express card (for those of you who don’t know what that is, it means you have a massive line of credit and you are probably filthy fucking rich).

But, for those humble souls who don’t have endless credit, for those who are war torn from the interview process and for those daring individuals who look forward to a monogamous committed relationship as if it was like crossing into Eden—dating sucks.

If this describes you, I have bad news. Now therapists are saying that married couples need to set up date nights. You can’t escape it. But, unlike death and taxes, it requires more work.

Hold on to your knickers because I am about to outline the ten reasons dating is like a weekend in Vegas with just you and your savings account. (I’m sorry baby, the house always wins.)

1. Profiling like a TSA agent: After you have been in the game for a while, you stop dating and you start profiling. It’s like being a drug sniffing dog on the Mexican border. Dating sites started it. I mean, the FBI started it. Then Facebook followed suit. Then everyone got in the profiling game.

 2. Dating Sites: Fuck, I have to fill out a five page questionnaire just to figure out if I am going to get laid or not. Back in the day, the most complicated choice I had to make was what type of underwear to wear, and whether I should shave my legs or not.

3. High Hopes & Low Standards: When your lead question to self is, Is this person I’m about to meet up with psycho?, it’s a dead give-away you are: A. Thirty-something, B. Divorced or C. Both. If you know more about the person than the cops do before you ever meet them, and if they are asking the question, Is my date psycho?, the answer might be yes. I would also like to say, this tendency towards psycho is not all your fault. I blame it on whoever endorsed Dr. Phil as an expert on relationships and then gave him his own T.V show. You know who you are.

4. Health Security Protocol: I swear to you they are going to start installing those x-ray airport-security-machines at Olive Gardens, Apple Bees, and truck stops. Fuck it, let’s just throw a colonoscopy in the mix for good measure. In fact, I will just bring my entire sexual health history to our first date. It hasn’t gotten to this point, but I imagine that during some insanely horny moment, this conversation might take place: “Do you have an STD and is it curable?” “Yes.” “Well, in that case, there will be a service charge. I will just send you the clinic bill.” (Yes, it’s a whole new level of desperate. I’d die alone in my cabin in the woods, surrounded by my twelve cats and have them eat my rotting carcass before I ever crossed over into code-WTF-desperate.) Now that we cleared that up—pun intended—let’s move on.

5. Biological Clock: From age 28 to now, mine has sounded like Big Ben. But, I don’t want babies. I just want to practice making them all the time. I want to drown myself in sex. If there are fifty shades of grey and five colors of fucking, I want to taste the rainbow.

Photo: Wickipedia

6. Children: I have mad respect for parents; especially single parents. And dating while raising kids is like playing the worst game of Go Fish ever. The whole time you are thinking, “Does my date have the cards I need to make a set or don’t they?” If both consensual parties already have kids then it becomes the craziest game of Gin-Fucking-Rummy ever known to mankind. You win Gin-Rummy when you get two sets of three and four of a kind. In relationship terms, it is a blend of kids, parents, extended family and partners. The only other place that has more combinations is Baskin Robin’s 31 Flavors of Ice Cream.

7. The Economy: Who pays for shit? Do I? Does he? Do we both chip in? A date used to mean a free meal. Well, it was sort of free if you don’t think of a hand job as work.

8. Epic Fail. Date number one consists of dinner, entertainment, and maybe some cocktails; maybe even several cocktails because you were so nervous you forgot your own name. That fifth Cape Cod you drank was just to take the edge off. Now, you not only have the pleasure of nursing a hangover with massive amounts of Gatorade, you also get to use it to wash down your Plan B pill. (Plan A—manifest your fairytale life like a genie—clearly hasn’t worked out.)

9. Aging. Have you seen some subtle changes in your body? Maybe some white hairs have started to show up and have made you quietly wonder, “Am I turning into a wizard?” Maybe your skin has started to grow moles at a rate that has you asking, “Am I part witch?” When hair removal becomes a part-time job and you are starting to consider adding lasers into the mix, Ponce de Leon doesn’t look so stupid does he? (Further, as a woman I have to say our breasts start to do really weird things. If mine received a report card every month, one would get a B- and the other a C+. When this happens, the lyrics to the Janis Joplin song, Get it while you can take on a whole new meaning.)

10. The 50/50 statistic: Hey, the date could be one of the best nights of your life. In fact, it could even lead to a meaningful relationship, children, a mortgage and deep spiritual growth. But, if you take this thing all the way to the altar, you only have a fifty percent chance of sticking it out. In different terms, you are walking into the hospital with a terminal illness and they are fifty percent sure a cure will be invented in time to save your life. Hey, fuck it right? Put on your best hoe gear and slap on your best pretty. Go get’em tiger!

After reading this you may have wet your pants from laughing or you might be puking from utter disgust. Either way, I say go get your Journey album and crank it up. Don’t stop believing!

Authors Note: Okay, okay, after the last article and this one, I can see how I am painting a bleak picture. I became a therapist because I get it. Life is full of challenges. As a therapist, I help individuals rise to the challenge time after time. Some of my clients have been my greatest teachers. I am honored to be a witness to the power of the human spirit. Thanks for reading! 

relephant reads:

The Number One Commandment of Dating.

The Dating Games. 


Editor: Lori Lothian

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Rebekah Freedom

Rebekah Freedom McClaskey is a Breakup Specialist and psychic. She offers one-on-one counseling in person and over the phone as well as hosts Breakup Rehab Support Group. She has a master's degree in transpersonal counseling psychology from Naropa University. Rebekah is passionate about using her extensive knowledge of love and relationships to set people free. Listen to her podcast. To work with Rebekah visit her website and catch up with her on Facebook.


25 Responses to “10 Reasons Dating Sucks. ~ B. McClaskey”

  1. Annie Ory says:

    You made me laugh.
    From a former Dating & Relationship Coach, I find it helps a LOT if you just decide you're going to have fun, and laugh anyway, even when it's ridiculous. After all, everybody needs somebody. Sort of.
    Some of the most awesome stories I tell are of dates that went bad. I laugh now. The trick is to laugh when it's happening.

  2. Oh, girl. You bring it. I love reading your writing. Clever, funny, down-right shocking. 🙂 "Dating use to mean a free meal. Well, if you don't consider a hand job work." "Put on your best hoe gear and slap on your pretty." Or, my fave, If there are fifty shades of grey and five colors of fucking, I want to taste the rainbow." Damn girl. Gimme more.

  3. J.R. says:

    Rebekah both your articles are awesome, good therapy, laughter always works. Thanks

  4. Laura says:

    I love this lady!!!!! BRILLIANT sharp provocative edgy sexy writing. you go girl!

  5. Katherine says:

    another fucking awesome post!!
    I am madly, irrevocably, in love with you.

    • yoga bear says:

      C'mon Katherine(language)
      I am just an old man I guess but it is hard to diagree with you. Nice to have something make you laugh through the day and for that I am grateful

  6. Orin Hahn says:

    After reading this one after the last Im beginning to see the self effacing humor below what I took initially as just bitterness and frustration. Sometimes a giant bucket of wtf it ain’t fair needs to be bailed out of your ship before it sails well. As a divorced guy with a kid who had to first learn about courting, seduction and dating at 30 you stir up memories of just how laughingly awful it all could be. It has turned out quite well, in fact I even now enjoy sharing those terrible memories with my 14 year old as she asks what’s dating like?
    Keep your sense of humor and here’s wishing the biggest richest soul shattering orgasm comes your way ( pun intended too ) to shake off all the frustration, stir your spirit and give you a glimpse of all that’s good about the stupid need we all have to find each other.
    Cheers and love to ya.

  7. sara says:

    Funny. Your view of dating is probably why you will never be good at it. I did a project where I went on twenty dates in twenty weekends and blogged about it. It was a great project because it forced me to not take myself or dating so seriously. Lighten up, but keep writing! Your articles are hysterical.

  8. Will Space says:

    In case you haven’t noticed the single person is the person most discriminated against these days. Being single is the new leprosy. In order to sell you more crap the importance of other meaningful relationships like friends, family, and the ones we make at work has slowly been sucked out without anyone noticing.

    Still the worst thing about dating is today’s white woman with her over inflated self importance and her tendency to twist new age beliefs into whatever she needs to insulate herself and pretend she can’t make any mistakes.

  9. Danielle says:

    You just made my Friday. This is incredible. Thanks!

  10. Lara Falberg says:

    Excellent article Rebekah! You sound like you write exactly like you speak, and that makes me wish I knew you. I'll look out for more articles from you!

  11. […] flags and think, oooooh pretty colors! Like Peter Pan chasing that pixie dust babe. With time in the dating war zone and some experience in the playing field, I see them now. I file them in the section in the back of […]

  12. JulienneG says:

    Well done! and I mean that sincerely. This comes from a nearly 3 month stint trying to cull the wisdom and compassion for myself in order to write about how dating can suck less. http://archetypist.com/2012/09/10/dating-survival
    I appreciate the chutzpah Ms. R!

  13. […] mention, those who belong to as many religions as you can imagine. Really? You are going to make a list of rules of how people should act on dates with one of 150 million females (and that’s just the U.S.) as if there is any one thing these […]

  14. […] she actually changed the use of the word ironic through the power of Canadian music. (By the way, the ex-boyfriend was a dick—this is neither ironic nor sarcastic—it is merely accurate. And yes, I may be […]

  15. […] with their own body via a daily yoga practice and then spun loose back out into the fish tank of dating […]

  16. […] other day my mom and I were discussing my tragic love life and the dude I was dating who just wanted to talk about his feelings all the time and got pissed […]

  17. LaurenD says:

    I seriously LOVE YOU! Hahahaha! You made my Monday by telling the absolute TRUTH! I am 40, single mom and there's so much to be said about every last thing you wrote. This is beautiful and I am sending it to all my single friends…"Put on your best Hoe gear and go get 'em tiger!"… You're the best!

  18. Dee says:

    I love this! I am smack dab in the middle of divorced dating with kids right now and can relate (and laugh) at every one of those things you mentioned. Still laughing…

  19. Gineen says:

    I am thirty something, divorced , and have a child. It honestly makes dating even more of a hell . And nearly impossible.

  20. Kait says:

    This is GENIUS!!! hahahahah! I thoroughly enjoyed this article! thank you :))

  21. Helen says:

    I’m a thirty-something single never married no kids and in the middle of the dating battlefield. Have to admit almost at the point of giving up lol. Loved your article and sense of humor! I’ll try to take dating less seriously to just give it a try.

  22. HBT says:

    Maybe our model of relationship in this culture is the problem. The idea that one person is supposed to meet all of our needs, and that we're supposed to be with one person..could that be the problem? Maybe there are other options.

    And I'm saying that as someone who's been burned by poly. I want a monogamous relationship. But I don't think it's in the cards. So I'm considering that my work needs to be around my expectations and assumptions about what love and relationship means.

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