A Twist of Date: Unexpected Lessons

when I don’t pay attention old habits are resurrected. They sneak in, dressed up in safe, common clothing like boys and food and shopping. Regardless of the substance or behavior, these are external ways to manage internal suffering…suffering that grows from craving more pleasure, craving less pain.

If there’s a no-fail strategy to win the online dating game, I’ll accept advice via email. Pictures…profile info… do they even matter? Descriptions are embellished, if not bold lies. Photos are old, filtered, or someone else’s entirely. A good friend of mine caught a guy using a pro MMA fighter’s pictures – not only false, but lazy!

Hobbies and lifestyles are exaggerated. I connected with a guy who claimed he loves cycling and hiking, but in person admitted his bike tires had been flat for two years. He didn’t hike- he worked 7 days a week. Our date became a working session over coffee; me as the life coach, he as my client. We both agreed we weren’t a match, but 2 weeks later I got a text saying he’d been out biking. To this day, I’d say it’s my most successful date.


A handful of people add “no drinking or drugs” to their profile description but I’m never quite sure how to take that. Do they mean ever? Am I eliminated because of my prior use and current probation? (Ugh. I hate saying that. It’s just not sexy at all). I usually assume I won’t be in their top 10, so I don’t even bother.

It’s controversial, and I approach cautiously, but I don’t consider guys who drink alcohol completely off my radar – Lyle was proof that sober doesn’t equal suitable anyway (see prev. post!) I do try to make it obvious I won’t be attending any keggers. “Lets go ski, then chat over drinks. Make mine a hot cocoa!” Millions of people imbibe without leaving a trail of wreckage; I don’t want to disqualify everyone based on my inability to moderate.

Reading through these profiles can make my head spin. Is he actually cute or is that just a good angle? Is that his sister or girlfriend he’s got his arm around? He seems too good to be true…so I know there’s something major wrong with him. Does he really have 6 cats, or is he being ironic?

Sometimes it seems I might as well just alternate swipes in rhythm to the radio. “Left, left, right. Right, left, right”.

There are a few non-negotiables though. Immediate disqualification if:

  • IPA is their favorite hobby
  • They are “420 friendly”
  • Favorite concert is a Phish show enhanced by “wicked good shrooms”
  • Does a little coke “but only recreationally!”

These are clear clues that we are not on the same page when it comes to mind-altering substances.

A ‘left swipe’ also applies to:

  • anyone who is “poly”
  • couples looking for a “unicorn”
  • the label “ethically non-monogamous”

I’m not a prude, and I’m an advocate for love in all forms. But these are clues that we are not on the same relationship page. Besides, after so many failed attempts maintaining a 1:1 relationship, I don’t have any business trying to multitask. I’m a big fan of campaigning for your specific desires and needs -but fail to advertise correctly, and you may have an awkward misunderstanding.

At least he’s being honest!

“Baron” is an attractive, child free, divorced man in his 30s who works with developmentally delayed adults. Could it get any better? Then we met. He spent our whole dinner expounding on his “unique and special” life stage. Baron was in the market for new experiences and would not be defined by labels or restricted by customs.  His ex-wife was controlling and jealous; he craved freedom, autonomy and variety. “I’m not POLY exactly, but I won’t discount it.” Baron told me “You could call me ‘ethically non monogamous’, but I consider myself even more specialized. By the way, I should tell you that I have a standing sex date on the weekends with my best friend. That won’t stop if you and I start seeing each other.” Duly noted. No need to stop on my account.

Baron clarified further…His busy schedule left no real time to “date”, but he would make time to fit me in if we continued to “click”. Thursday nights were open on his calendar, maybe I’d like the time slot?

This wasn’t a date, it was an interview for an unpaid escort position. Complete with promotion potential to unpaid prostitute if and when we decided to initiate sexual activity.

Listen, Mr. UNIQUE ….. You were jilted by your one true love. Your 20s were a sacrifice to a ball and chain instead of sewing your wild oats, and you’re making up for it! It’s cool, you be you! I’m not looking for lifelong commitment either. But I am also NOT an appointment in your daybook.

To be fair, his profile had offered hints “If you’re looking to marry Mr. Right, it won’t be me. My circumstances are unique.” “I’ve chosen not to have children; my situation is unique to me.” I guess I ignored the annoying verbiage because I’m not hunting for Mr. Right, and I don’t want more children. Besides – he was hot, a volunteer for special needs kids, and available on Halloween night. But the appeal was outweighed by his narcissistic monologue over french fries. You’ll be shocked to know I declined the offer for date #2. Also, he was nowhere near as hot as his pictures implied. This was becoming a pattern.

As for “ethical non monogamy”… The concept isn’t too far fetched for me (at this unique stage in my life, LOL!!!) but something didn’t feel legit. His superior attitude toward monogamy; his need to schedule our time together. And I couldn’t get over my concern for his “best friend with benefits” who only gets him on the weekend. Should she be on the date with us, approving the schedule? Does she know he’s online? Is she aware of how unique he is?

To top it all off, he didn’t get my Halloween costume at all. I had to spell it out and he still didn’t get the reference. Helloooo???!!?? I’m Tiffany!!!!

Even my toenails were little blue boxes with white bows! (Special credit goes to Hannah-  frantically shopping with me on Halloween day, looking for a shirt the exact shade of “Tiffany blue”  ❤️❤️❤️)

This date had potential….but the Halloween “treat” felt more like a “trick”. It was the last real date I’ve been on. I started thinking…. I don’t want a serious boyfriend, but I’m not game for one night stands. Baron’s offer seemed like a practical compromise, but I wasn’t enticed by that either. What do I want?

My inner Tiffany has been prodding me since….why am I dating? And why these guys, why not be more discerning? If I ever write a book, this chapter will be titled “Dating: Quantity not Quality”.

A few consistencies rang true as I reflected on my dating habits:

  • Impulsive – signing up for multiple dating apps. Dating the first week I was single. Driving hours to hike overnight with someone I’d never met. All in, 100%.
  • Compulsive – going on dates even though I knew it wasn’t in my best interest. Telling myself I would take a break and focus on me, then scheduling 3 dates in the next 5 days.
  • Inability to deal with stress – Rough day? No problem, Swipe right! I’ve got a date!

Google “traits of an addict” or “addictive personality”. There’s no denying the truth of my actions, all under the guise of “saying yes to opportunities” and “being optimistic”.

I just need MORE dates to make me feel better. It was becoming no different than my use of substances. That next drink will make me feel good; not tired and hungover like last time. That next pill will make things better; not leave me craving more. One piece of cake becomes a whole cake (or in my case one piece of pizza the whole pie). The next date will make me happy, not disappointed and filled with self loathing. I’ll just drink/take/eat/buy/date one more, and tomorrow I swear I’ll take a break. But for now, I need that next THING to avoid my feelings…to quench the craving…to fill the void.

What emptiness am I filling? What feelings am I trying to avoid?

18 months into recovery and I’ve been feeling healthy. But when I don’t pay attention old habits are resurrected. They sneak in, dressed up in safe, common clothing like boys and food and shopping. Regardless of the substance or behavior, these are external ways to manage internal suffering…suffering that grows from craving more pleasure, craving less pain.

img_8211 Dammit. Seriously. The first couple drafts of this blog did not end this way. This is real time reflection….You’re watching the show live.

My date with Baron felt like a waste of a great outfit. But maybe it was a beginning to the end of a dangerous spiral that was heading more towards addiction than adventure. I thought this blog shared funny anecdotes about filtering out profiles and being clear on boundaries. Suddenly I’m exploring cross addiction and unearthing my hazardous behaviors.

Uff da. I’m officially blogged out for tonight! Time to try turning inwards. To try unraveling these maladaptive dating decisions. What will I find in the space that feels so empty? No guarantees I’m going dateless though! Progress, not perfection.

Cheers and gratitude,

Tiffany & Co.

3 thoughts on “A Twist of Date: Unexpected Lessons

    1. Thank you! It’s always heartwarming to hear that my shade of humor is appreciated, and that it helps others a bit when I share my ups and downs. Never stop trying! Tiff


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