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This weekend, I’ll hop on a bus and ride it for 10 hours, into another country, where I’ll have my first out-of-homeland threesome. We’ve been planning it for six weeks. Those weeks have felt like years.

See, both of my previous threesomes were impromptu – happy accidents of timing and circumstance. This one was deliberate, chosen, considered. I can see the merits of both approaches: spontaneous sex gives my anxiety less time to take root and psych me out, while long-haul schemin’ allows for excitement to build like a pre-record-launch hype campaign.

Any activity is more fun if you’re doing it with people who love it. That’s true of sex, and it’s also true of planning sex. Both of my threesome co-conspirators in this case – Bex and a gentleman friend of ours – are as nerdy about sex as I am. This made our brainstorming, scheduling and co-ordinating into a delightful process, like planning a party… except with more sexting.

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The Negotiations

When you think about sex critically and deeply on a regular basis, you become more aware of what you want, what you like, what turns you on – and what doesn’t. Once you know what you want, the next step is to ask for it. That can be scary sometimes: our carnal cravings are so close to our hearts and entrenched in cultural shame that often our inclination is to downplay our desires. But I’m lucky enough to be having a threesome with two people I deeply trust, who I know would never shame me for articulating what I want.

In weeks of chatting and spitballing, we came up with some mutually exciting activities to include in our threesome docket. And the best part of it is, all three of us are so easygoing and invested in each other’s enthusiastic consent that we know we can abandon anything on the list if it feels wrong on the day of. “We’ll just be like a bunch of little puppies,” dude said to me in one of our many excited exchanges about threesome logistics. “We’ll try stuff out.”

Bex and I are solely-platonic friends who engage with each other sexually on a very limited basis, so part of our negotiations involved setting boundaries for what we will and won’t do to each other. Fortunately, we were on the same page about everything we discussed: we’re cool with doing a double BJ, making out, and some boob stuff, but below-the-belt action is off the table except for maybe manoeuvring dildos.

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The Feelz

Sex nerds understand that sometimes sex stirs up feelings, and the best defense against icky feelz is to talk them out, before, during and after your experience of them. Good communication where everyone feels respected, heard, and valued = good sex, with minimal drama.

The dude in our trio is someone with whom I have sexual history. He also gives me hella heart-eyes feelings, and I sometimes struggle with jealousy when I really like someone. Both he and Bex repeatedly made sure I was okay with “sharing him,” before and during the planning of our ménage. Though I might have felt gross if he’d jumped into the three-way headfirst without regard for my feelings, the amount of care he took with me put me at ease. As of right now, I’m not feeling a shred of jealousy – but I know that if I do feel strange on the day itself, I’ll have two friends there to talk it out with.

If you find yourself dealing with similar jealousies leading up to a threesome, think about what kinds of accommodations might help with that. I asked Bex if I could be the one to swallow dude’s cum after we blow him together, because being “rewarded” with jizz at the end of a beej feels satisfyingly intimate to me and I think I’d be sad if I missed out on it. Bex said yes, ’cause they’re an angel.

Bex has also recently started using they/them pronouns full-time and publicly identifying as non-binary, and that entered into our pre-threesome talks as well. Dude was amenable to learning about gender stuff, especially since he knows getting it wrong could kill the moment – so we talked about what pronouns, names and titles were and weren’t okay. Yay, respect and correctness!

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The Gear

I know all you sex toy nerds are curious about what I’m bringing, so here’s a rundown:

• Pegging may or may not happen, depending on the Whims of the Butthole. I’ve packed my pink Aslan Jaguar harness. Assuming we get the go-ahead, it could either be me or Bex who’ll do the fucking; we’ll see how we feel. I’ve also packed my bright blue Happy Valley Perk, because it feels the most like “my cock,” though I’m open to strapping on other dildos too.

• Dude likes using toys on people, and has proven his prowess at doing so. Bex and I think it’s hilarious to imagine him fucking us each simultaneously with our own Eleven or Double Trouble, so I’ve packed both of mine. Dual-wielding!!

• Vibe-wise, I’m bringing my Magic Wand Rechargeable and maybe my Tango. I just need something reliable to hold on my clit while dude finger-bangs me or pounds me with a toy or fucks me… Um, no, I’m not blushing! Why would you say that?!

• Bex and I like when I spank them, so that’ll probably happen during this threesome. They own all our favorite implements (including the almighty Pelt), so the only impact toy I’m bringing is my Maddie’s Dungeon wooden paddle, ’cause it’s cool.

• I threw my Ryder in there because last time I slept with this dude, he liked how tight my vag felt when the Ryder was in my butt. I am always eager to please.

• Like a Boy Scout, I am prepared as hell: my sex toy bag is topped off with dude’s favorite condoms, some lube samples, and black latex gloves.

Have you ever planned a threesome? What was the process like for you? (And what toys did you bring?!)

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Last year, I had a fuckbuddy who would tease me about being a size queen. I’d show up at his house toting my Eleven or my Double Trouble, and he’d jibe, “You seem to like big toys.” This always made me blush and deny his assertion, because there’s a certain amount of stigma that comes with being a size queen… but the other reason I disagreed with him was that his comment wasn’t quite right. I don’t like big toys; I like toys that hit my internal erogenous zones really well. And while girth or length can help with that, they certainly don’t guarantee it.

I thought about this a lot while testing the Tantus Sam, a new addition to Tantus’ outstanding line of dual-density silicone toys. The Sam was marketed explicitly toward fans of large toys. At 1.8″ in diameter and 7.3″ long, it is indeed pretty huge. Not the biggest I’ve had, but still substantial. However, for all its enormity, it barely even does what I need a dildo to do: hit my favorite internal spots.

imageThe texture of the Sam’s shaft is ridged with veins. They’re highly realistic-looking, continuing Tantus’ pattern of producing gorgeously convincing realistic dildos over the past few years. While the veins drag across my G-spot with every thrust, they also drag across my whole vaginal wall, so the stimulation doesn’t feel targeted. If I don’t use enough lube (or don’t reapply often enough), this texture can even feel abrasive.

The significant length of the Sam means I can’t get it all the way into me – not even close. When shoved in as far as it’ll go, the toy’s tip nudges my A-spot, but it’s not tapered enough to really get up in there. Sometimes I bash into my cervix with it when I try.

The toy’s coronal ridge frequently irritates my vag, catching on skin – just for a second, but for long enough that I register pain and get pulled out of the moment.

Don’t get me wrong – I’ve had some fabulous orgasms with the Sam. But it’s made me realize something about the way my vagina operates. Girthy penetration intensifies my actual orgasm, giving me something to squeeze around when those involuntary muscle contractions hit – but for the build-up to orgasm to feel good and get fast-tracked, I need a toy that hits my spots. Girth alone isn’t enough to make my vagina sit up, shut up and pay attention.

imageI think you’d love the Tantus Sam if your orifices like feeling filled up with something thick, and you’re not too bothered about targeting specific areas inside you. But if you want something realistic that can multitask a little better, I’d recommend the Uncut #1, Adam, or Maverick. They’re all in the same size range as the Sam but have curves and better-shaped heads for stroking G-spots or prostates. And none of them share a name with my dad, unlike the Sam.

Thanks for sending me this toy to try, Tantus!

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“This is a show about human sexuality, told from the approach of fun, enjoyment and pleasure,” the cheerful male voice chirped at me through my headphones. It said this at the start of every episode of the podcast. Today’s would be a good one; Kidder was going to talk about exhibitionism. I was excited; I had so much to learn. “It’s a rational conversation, but it’s for adults,” the voice continued, “so if you’re a younger listener, please go to Scarleteen.com, where you can learn about your body and your sexuality in an age-appropriate setting.” I was twelve years old. It didn’t matter. I knew I wasn’t like the other middle-schoolers. I was sex-positive.

I’d been interested in sexuality for as long as I could remember, scrawling erotica in my Anne of Green Gables diary, hunting for “vagina” and “clitoris” in the indices of library books, and researching masturbation techniques on my family’s shared computer when my parents were asleep. But until I discovered Kidder Kaper and the Sex is Fun podcast he co-hosted, I had no unifying ideology for all my jumbled thoughts on sex. Kidder made me feel like being a sexually precocious preteen was actually a good thing. As I absorbed his podcast between eighth-grade classes, or late at night in bed, I began to feel like less of an immoral pervert and more of a sex-positivity activist in the making.

Ask me what it means to be “sex-positive” now, and I’ll rattle off a pat answer about consent, boundaries, acceptance, and exploration. But back then, I didn’t have language for what I felt. I just knew that Kidder’s approach to sexuality felt innately right to me. He and his podcast cohorts enthusiastically accepted each other’s kinks, even (and especially) the ones they didn’t share. They talked about their vibrant sex lives without shame or regret. They explored questions like “Why are people into that?” and “What gets you hot?” rather than propagating stigmas or taboos. They talked about sex in a way I’d never heard before, and I truly believe they rewired my brain permanently. I can’t imagine I’d be doing the work I do now if I hadn’t obsessively devoured the Sex is Fun podcast in my early teens.

Flash forward 12 years or so. I’m an adult now (well, a confused kid who is legally and technically an adult but still doesn’t feel like one). When some sex blogger pals and I were planning a road trip to Minnesota, I pondered the question, “What’d be fun to do in Minneapolis?” A few weeks before the trip, I suddenly remembered: the Sex is Fun crew lived in Minneapolis. Or at least, they did, way back when they were doing the podcast. Who knew where they’d ended up?

I started doing research. Kidder had left the podcast many years earlier, and the show itself had ended a few years after that. I checked Kidder’s social media accounts, scanned the podcast website, Googled incessantly, but it seemed like the person behind Kidder Kaper had checked out of that pseudonym long ago. It frustrated me that I didn’t know any useful information about him – his real name, his real-life occupation, even the real names of his co-hosts on the podcast – so, while he probably still existed somewhere in Minnesota, I couldn’t get to him. I couldn’t tell him how much he’d meant to me when I was 12, how much he still meant to me. I resigned myself to a Kidderless trip to Minneapolis.

However, the night that we arrived, I mentioned my quest to our Minnesotan friend Calvin over dinner and drinks. “I’m looking for this guy,” I said. “He wrote the Sex is Fun book.” Immediately, Calvin said, “Oh, Kidder?” and my eyes practically fell out of my head. He knew him!

By the next day, Calvin had gotten in touch with Laura Rad, one of the other hosts of SiF, to get Kidder’s contact info for me. Bex texted me while hanging out with Calvin: “So, uh, if you wanted to talk to Kidder, here’s his number… Apparently he said he’d be down to get coffee.” Upon receiving this message, I threw my phone down on the kitchen table at our Minneapolis Airbnb, shouted “WHAT?!” and then proceeded to panic about what to do next. (#AnxietyLyfe, am I right?!) I’m proud to say that I managed to text him without breaking down in anxiety-tears… although did cry later in our conversation when he referred to me as a member of “the next generation of sex educators/activists/authors [who] progress sex-positivity.”

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The next day, after a morning of touring local sex shops, Bex drove me to the café where Kidder and I had agreed to meet. My outfit consisted of a collar, vulva ring, and what Bex calls my “boob dress,” because, well… when you meet your sexuality hero, it makes sense to dress sexy in every sense of the word. As I crossed the street and walked into the coffee shop, I could feel my heart hammering in my chest. I bought a hot chocolate and my hands were shaking too much to even hold it properly.

He arrived promptly, and I recognized him immediately, even though the few pictures I’d seen of him were from years and years before. We said hello, hugged, and launched into conversation. Kidder is intense, brilliant and loquacious, just bursting with ideas and opinions; that was true when he hosted the podcast and it’s still true now. We talked for hours about sex (of course), relationships, the internet, technology, my blog, his work, squirting, butt stuff, and so much more. He’d checked out my blog and he complimented me on my “witty” and “self-aware” writing, and when I showed him a screencap from a porn scene I performed in, he told me he thought I looked like Bette Davis. I haven’t blushed that hard in months.

Some people say you shouldn’t meet your heroes, because they’ll inevitably be human and flawed and that’ll just disappoint you. I worry about that a lot, because I’ve met some of my heroes and I’ve also met people to whom my work has been important. But I didn’t experience that with Kidder – maybe because he’s always been so honest about his struggles and shortcomings. Even as a fresh-faced eighth-grader, I knew that my sex podcaster crush/idol was arrogant, stubborn and a little bit bonkers. He’s still that way and I still love it. Meeting him and talking to him just made me more certain of that.

We talked for so long that the café employees announced they were closing for the night. But it still felt like there was more to say. He offered me a ride back to where I was staying, and even though it was a 15-minute walk at most, I said yes. He suggested I text a friend to fill them in on my whereabouts, and acknowledged that it was okay if I didn’t feel comfortable getting into a car with a strange older man, but he didn’t feel strange to me. His wisdom and wit have helped motivate my mission all these years; he feels close to my heart, ingrained in my brain. I trust him.

“Alright, let’s throw down the gauntlet,” he said. We would cap off our conversation by asking each other five questions each, and the answers had to be honest. We talked about virginity, death, regrets, nanotechnology, fisting, blowjobs, and Steve Jobs. I felt myself straining to absorb his smarts like a sponge.

As Kidder pulled into a parking space outside my Airbnb, we each had one more question left to ask. He turned to me, both of us still sporting seatbelts, and said, “You wanna kiss?”

Though I’m officially agnostic, I believe in a sentient universe to some extent. I believe that our fondest wishes and deepest yearnings create changes in the great cosmic order, and that we are sometimes delivered the manifestations of our hopes. Sometimes what we want manifests in ways we could never have predicted or planned, because the universe’s genius extends far beyond what our human minds can formulate. This moment in Kidder’s car felt like the fulfilment of an old, old wish. I could feel my tiny 12-year-old self, somewhere deep inside me, looking enviously forward in time. I wanted to tell her: Look. Look at this. You’re confused now – you feel like a freak, a weirdo, a pervert – but there are people like you. And some of them will think you’re beautiful and brilliant. And that guy you listen to on your iPod, who makes your stomach feel fluttery and your brain feel bouncy? One day he’ll think you’re pretty nifty too. And he’ll even want to kiss you, if you can believe that. So just hold tight. It’ll all be okay.

Kidder kissed me, and it was an amazing kiss. But it was also more than a kiss.

When it was done, we got out of the car and took some silly selfies together. Then we hugged, and he wished me a good trip and a safe journey home. We said our goodbyes. I walked into the Airbnb, where my friends were waiting excitedly to hear what had happened. And I burst into tears. Because, gosh, 12-year-old me would just be so goddamn excited if she knew.

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Did you know that Toronto is one of the up-and-coming porn hotspots of the world?

Well, sorta. We’re no L.A., but there’s some exciting stuff happening here in the realm of indie porn. And there’s an event coming up that’ll prove it.

SMUT in the 6ix is a “magnificent celebration of perviness” masterminded by Caitlin K. Roberts of Spit, Samantha Fraser of Playground Sexuality Events, and Sophie Delancey of Tell Me Something Good. It’s happening next Saturday, the 14th of May. Here’s six reasons you should buy your ticket now and join me there…

The panels.

SMUT’s daytime programming consists of four panel discussions on topics related to porn. These sessions will cover several aspects of #PornLyfe, from social stigma to diverse representations to camera skillz.

They’ve got a ton of great speakers lined up, including MakeLoveNotPorn.TV curator Sarah Beall, CinéSinclaire bosslady Kate Sinclaire, and indie porn darling Rebecca Deveaux, among others. And – drumroll, please – I’ll be moderating one of the panels! So you’ll get to see me being a Smartypants McCutieface. Bonus.

The performances.

SMUT’s nighttime gala will feature burlesque, spoken word, live music and dance. All the performers are local and you can be assured their acts will be appropriately smutty. Emceeing the evening is Dane Joe, who I can tell you from firsthand experience is charming as hell. (And also knows how to wield an Eleven like a fuckin’ champ. Unf.)

Plus… I’ll be performing, too! I’m gonna bust out some dirty ukulele songs. You don’t want to miss that, surely?!

The party.

The gala will have DJs, dancing, and general merrymaking. S’gonna be a hoot!

In particular, I’m interested to see what everyone will wear! The sartorial intersection of “fancy” and “smutty” is always an interesting one.

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The babes.

There are soooo many attractive people in our local porn scene. And I’m using the word “attractive” in a deeper sense than just the physical one (though they are visually babely, too). If you (like me) are attracted to smart, funny, easygoing, sex-positive, feminist cuties, you’re not going to find a better event to get your flirt on than SMUT in the 6ix.

The porn.

Of course, no porn-centric event would be complete without, y’know, porn. Rebecca Deveaux and my pal Taylor J. Mace are curating and co-presenting a selection of homegrown porn at the event. If you’ve never watched porn in a roomful of people before, you should – it’s a unique experience, and can be a lot of fun!

The bragging rights.

Spit‘s going to be a big deal in the porn world one day, and so is the city of Toronto! Get in on the ground floor of our burgeoning indie porn scene, so you can say you liked Toronto porn before it was famous.

 

Check out the SMUT in the 6ix website and then buy your ticket! At just $37 for the whole day, it’s one of the cheapest sexuality conference tickets I’ve come across. I hope to see you at SMUT; make sure you say hi if you spot me!

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In mid-February, I couldn’t stop crying about boys. All in a row, I’d crossed paths with a series of people who I adored, who felt almost mystically perfect for me, who nonetheless couldn’t or wouldn’t date me for various reasons. Such is life, I suppose. And although I knew I’m worthy of desire and would find someone awesome eventually, and although I kept telling myself “This too shall pass,” tears still kept pouring down my face as I sat in bed wailing along to Missing Ember.

“It has been a year and a half since the end of my last relationship,” I wrote in my journal, “and whereas that break-up initially made me feel wonderfully free and independent, now I just feel weirdly unmoored. I miss the emotional support and consistency of having a primary partner.”

After writing some more and effectively soaking my journal with tears and snot, I fired off an email to Carly from Tiny Lantern Tarot. (Carly uses both she/her and they/them pronouns, so I’ll be alternating between those.) I had read an interview with Carly on Up, Down & Out and loved her nonjudgmental, intuitive and queer-friendly approach to tarot, and since my emotions were so tumultuous at that time, I felt I needed some direction. Some types of emotional turmoil call for a visit to a therapist, or a long phone call with a best friend, but for some reason I craved advice from someone wise and witchy. “I have some concerns around romantic and sexual relationships in my life that I would love to get some guidance on,” I wrote in my initial email to Carly.

A few more emails and a couple weeks later, I headed to Carly’s home office for my reading. They made me tea and we sat on their little couch. We talked a little bit about my concerns around romantic relationships, and then she drew some cards.

Carly uses the Collective Tarot, a deck whose illustrations are bursting with queer people, people of color, and a diverse array of bodies. This immediately felt right to me. Tarot cards are usually traditionally gendered and free of flagrant sexuality, and my life is… not those things. Carly’s calm manner, and the cards themselves, affirmed to me that this was a safe space for me to talk about my queer/sexy/kinky life, if need be – and that’s important, when you’re getting a reading about relationships!

Two of the four cards Carly drew were major arcana cards and the other two were face cards, which they told me meant the issue at hand was an important one to me. It certainly was!

The card at the center represented “the heart of the matter,” and it was the Seeker of Feathers. Carly explained that this card is about communication and assertiveness. “It’s more important that you say the thing,” she explained, “than that you say the thing nicely.” I’d gotten into a habit of downplaying my needs, of telling people I was okay with my romantic and sexual entanglements being “chill” and “casual,” when actually I wanted something more. This card told me to be more honest with potential beaux about what I want – and I interpreted that to mean honesty about not only my feelings but also my desired relationship structure (non-monogamous) and the kind of sex I want to be having. I’m not always good at communicating my needs if I think they might ruffle feathers, so this card reminded me to do so regardless.

The card on the left represented “what to do.” It was the Code, which features what appears to be a queer kinky person flagging red for fisting. (So, so, so awesome.) Carly told me that this card refers to boundaries, borders, and communities, and recommended I consider the communities I run in: in what ways do I fit into them, and in what ways do I stand out? In the places where I stand out, do I want to accept that and be proud of it, or do I want to adjust my approach so I fit in better?

This card made me think about how often I feel like a baby/newbie/impostor in the sex-positive communities I’m in. Though I’ve been running in these circles for years, it’s still hard for me to accept that I’m a valued member of the Cool Kids’ Club. I’m well-liked and respected by the members of that “club” who know me; there’s really no reason for me to feel like I don’t belong. This card reminded me that I should dive even deeper into that scene, unapologetically and enthusiastically.

Naturally, given the kinky content of the illustration, this card also refers to power dynamics. As we talked about my issues with anxiety and feeling out of place, Carly suggested that maybe I need to develop a power dynamic with myself: be my own dom, so to speak. This might involve bossing myself into doing stuff that is slightly uncomfortable for me, but will help me grow and meet potential partners – like attending social events that make me nervous, talking to new people, and entering new social scenes. I found it strangely helpful to have my anxiety re-framed in this way – as something I can challenge bravely if a cute toppy person tells me to, even if that cute toppy person is me.

The next card represented “what to think,” and it was the Apprentice of Bottles. Carly explained that this card usually evokes a person who is very charismatic, charming and shiny, but then turns out to be shallow and disappointing. They weren’t entirely sure what the card was trying to tell me, but it made a strange kind of sense to me: a lot of my emotional upheaval at that time had happened because I was idealizing people I had a crush on. Some of these people appeared to be my perfect partner, but of course, they weren’t actually perfect, and in many ways we would’ve been a bad match if we’d gotten together. I felt like this card was telling me to take people off the pedestals I’d put them on – and also to consider what qualities I actually need in a long-term partner, rather than just the dazzling qualities that capture my attention in the short-term.

Carly told me that this card can also refer to first impressions: making a big splash, and then retreating. We talked about how I often worry that the first impression I make is misleading. “I’m a sex blogger” is usually one of the first things I tell new people about myself, and I think it gives some people an incorrect impression about my personality, my priorities, and what kind of relationship(s) I might be looking for. Carly encouraged me to experiment with the way I talk about myself – which I started to do later that night, by removing the phrase “sex blogger” from my Tinder profile. I figured it’ll be easier for me and potential matches to discover each other organically if I roll out information about my sexuality more slowly. (Preliminary results: Tinder dudes have indeed been less skeezy and more curious about me since I did this. Innnteresting.)

The final card represented “what to avoid,” and it was Strength. Carly told me this card refers to strength not in the traditional/brawny sense, but in the sense of emotional bravery and vulnerability. At first, she was puzzled that this card came up in the “what to avoid” slot, since obviously, these traits are usually a virtue in relationships. “The only thing I can think,” they said, “is that maybe you have a pattern in your dating life of being too vulnerable and open, of letting too many people in too quickly.”

I almost started crying when she said this, because it was so amazingly true and there’s no way Carly could have known that. I give far too many people the keys to my emotional kingdom, and it results in me getting hurt a lot. When I choose to invest emotionally in someone I’ve just met or barely know, at first it feels like an exciting rush, but it quickly gets heavy and painful, with very few exceptions. “Vulnerability is necessary,” Carly told me, “but not everybody deserves your vulnerability.” They were so right, and I made a promise to myself to be more careful about getting invested in people who haven’t yet proved they deserve my heart.

I left Carly’s house with an immense sense of clarity and inspiration, like I’d just been given the road map to my next stop on life’s path. The despair of feeling unloveable had lifted. I was still just as single, my life just as devoid of serious romantic prospects, but that felt less important and less permanent than it had before.

Now, here’s where shit gets weird. Two days later, I met a boy on Tinder. We went out. We hit it off. We started dating. I leapt headfirst into a relationship with him, before knowing if he even ticked all the boxes that matter to me (“Is he a feminist?” and “Is his sex drive compatible with mine?” being the two key ones in this case). I was so desperate for a boyfriend that I viewed this dude idealistically, filling in the blanks and paving over problems to round him up to a person I could date.

I should have communicated my needs more clearly, more quickly. I should have held out longer before calling him my boyfriend and pinning my hopes on him. I should have remembered that first impressions aren’t everything and people change as you get to know them better.

These are all things that Carly told me in my reading with her. But it was like the universe wanted to hammer these points home. And hammer, it did.

In the end, I learned these lessons the way I learned so many math and science concepts in school. Someone smart explained the lesson to me – and then I had to put what I’d learned to use in the real world.

Well, I sure learned quick. I won’t make those mistakes again. And if I do, maybe I’ll pull a few tarot cards to learn how to fix it.