Over the last couple of years, we’ve been talking about how to improve your dating life, from making yourself look better, improving your ability to approach and charm friends and strangers, fixing the attitudes and self-limiting beliefs that hold you back and even how to find more sex. However, while it’s good to learn about each individual aspect of attraction, dating and self-improvement, you need to be able to blend them all together. After all, getting better at dating is a holistic system rather than simply applying each of the component parts one at a time.
However, trying to apply everything all at once can feel overwhelmingly complicated. It helps to have some context in which you can see how everything merges seamlessly. So with that in mind, the Doc is getting back on the examining table to study another incident from his life to see how to put all of these lessons together. It’s time for another Anatomy Lesson.
And this time, it’s a story of how I escaped the Friend Zone.
We’re going to look at how I took a decades-long platonic relationship and went from “just friends” to so much more – and more importantly, we’re going to break down WHY what I did worked… and how you can relate it to your own experiences.
Some obligatory ass-covering – this has been approved by all parties involved. Certain details have been changed to protect the innocent and not-so-innocent.
And so I give you: The Great Escape.
I met Cat on the first day of classes of our Freshman year of college – the only class we would ever have together, in fact. It was, amusingly enough, as classic of a “meet cute” as you could want: she had gotten lost trying to find the classroom and arrived 20 minutes late – well after class had started. Because of a scheduling foul-up, there were more students than there were seats. Cat, having arrived last, was going to be stuck standing for the rest of the class. I, never one to miss an opportunity for a grand gesture1, I gallantly gave her my seat and spent the rest of class trying to lean up against the chalkboard in a suitably cool and manly fashion.
I later had to wash my shirt three times to get all the chalk-dust out.
After class, Cat and I started talking… then headed over to the Student’s Union to keep talking. Then met up with friends at the dining hall.
Over the course of the 8 or so hours that we spent together just hanging out and chatting, we realized we loved almost all the same things and had absolutely insane nerd chemistry and we were destined to be best friends.
I also discovered she had a boyfriend of three years.
As a result, I did something completely unlike me: I mentally shuffled her into the “Good friend” category of my brain rather than “potential girlfriend” category. In fact, as hard as it is to believe, I genuinely didn’t harbor any romantic or sexual feelings for her. She was quickly becoming my best friend and like the sister I never had. We spent practically every day together, hanging out between classes and at meals, indulging in the usual college rituals with our circle of friends. We would joke that in some alternate universe we were a completely scorching couple but in the real world… we loved each other dearly but genitals never came into it. In fact, the next year, she would be the one to introduce me to my first serious girlfriend.
Graduation came and went and we moved to opposite sides of the country. We would only see each other twice in person during the intervening 12 years, but thanks to cheap minute plans and the wonders of email and instant messaging, Cat and I never fell out of contact.
The important part here was that Cat and I were genuinely friends. While I’d had many occasions – before and since – where I made the classic “Nice GuyTM“ move of trying to pull the Platonic Back Door Gambit, I legitimately only thought of her as a friend. As a result: I was always able to be completely honest and genuine with her, rather than pretending to be her friend under false pretenses. It would also potentially make things more difficult: after all, we had literally over a decade of my being “Good Ol’ NerdLove”, the guy she spent all that time thinking of in entirely non-sexual ways.
In the years that passed, Cat and I only managed to meet up in person three times; first at her wedding shortly after graduation, then a New Year’s Eve celebration six months later and again two years after that. However, while we were separated by thousands of miles, we were in touch almost constantly – regular emails were exchanged and nearly monthly phone calls. Between the two of us, we stayed in contact through five separate moves, three deaths, four jobs, applying to grad-school for her and three serious girlfriends on my part. She provided much-needed support through some ugly break-ups and long dark nights of the soul, while I helped talk her through homesickness, self-doubt, anxiety over trying to get a PhD in History and the trials and tribulations of married life
During this time, I had begun my transformation from hapless loser to the man I was today… and Cat was a long-distance witness to it all. She got all of the juicy details of my escapades in Austin, from the girls who broke my heart and set me on my path to the trail that I started to blaze through the bar and club scene. She used to joke that she was enjoying having a vicarious window into the dating scene – after all, she’d been with the same guy for nearly 9 years by then. She remarked that she could tell I was becoming much more confident and outgoing than I ever had been back in college.
“It’s nice to see you finally coming out of your shell,” she told me over the phone one night as I told her about a long night spent getting bottle service at a local club. “You never would’ve even dreamed about doing anything like this back in the day.”
How very true.
Back in college, I was – if not withdrawn – very unsure of myself. I had my identity as a nerd and that was that; I was never going to be the Guy Who Was Good With Girls, no matter how much I wished I was. Years later, it was almost laughable how wrong I was.
But while Cat had heard the stories, she still hadn’t seen the difference for herself.
This would change soon.
One of the trickest parts of transforming a platonic friendship into a sexual or romantic relationship is having to break the other person’s mental image of you – after all, that image is intimately tied into whether or not she sees you as a sexual being. If someone has spent months or even years seeing you strictly as a platonic friend – even as a surrogate family member – then it can be very hard to switch gears to seeing you as someone they might conceivably want to be naked with.
The tricky part of breaking that mental image is that change is gradual and slow. The idea of Suddenly Sexy is popular, but in reality, that transformation requires more than whipping off some glasses and a more flattering hairstyle. It takes time and effort, and for someone who sees you on a daily or even weekly basis, they may not even notice the evolution. When someone has a fixed image of who you are, slow changes often get absorbed into the status-quo rather than providing that “Good heavens, you’re beautiful!” moment you’re hoping for.
This is why distance was one key component to my escaping the Friend Zone; it gave me time to change and grow without those changes being a part of our status-quo. As a result, the differences between who I was when we met and who I was now was that much more pronounced in her mind.
But more on that in a moment.
The Build Up
One fateful day, Cat dropped a bomb on me: she and her husband were splitting up.
This caught me entirely by surprise. As far as I knew, she and her husband had been – if not deliriously happy – at least doing well. I knew that the stresses of grad school were getting to her2 but I had thought this was just the usual “too much work, not enough hours in the day”.
As it turned out, nobody knew; she had spent the better part of her entire relationship masking the fact that she was unrelentingly miserable. Her husband was emotionally manipulative at best – borderline abusive at the worst and the only reason why she’d went through with the marriage in the first place is that she felt as though she couldn’t back out now… religious and social upbringing meant that this was the only choice she had.
Divorcing him however, turned out to be the best decision she had ever made. It was like a great weight had been lifted from her shoulders – I could hear the relief in her voice whenever we would talk. There wasn’t a period of adjustment; it was clear that she was over the marriage long before the papers had been signed and she was reveling in her newfound freedom… at least as much as grad school would allow, in any case.
Our own relationship took an interesting turn at this point. Over the years since I had what I call my Batman moment ((“Yes father! I shall become… a pick-up artist!”)), I had become much more flirty in my daily life. If you were a woman and I was having a conversation with you that lasted longer than 5 seconds (and didn’t involve my having to explain why I needed my power and/or credit cards turned back on) then I would flirt with you. There wasn’t any serious intent behind it; it was just part of how I interacted with people. I enjoyed the playfulness of it, the back and forth bantering and teasing.
My conversations with Cat were no difference. I’d flirt with her when we’d talk over IM or on the phone, she’d laugh and make jokes back and we’d go on with talking about Buffy or Firefly or our cats. It became part of the background radiation of our relationship.
After her divorce, she began to flirt back a little more than normal, teasing and joking in ways that she hadn’t felt free to do so before. She was enjoying the feeling of being single again and being free to do what she wanted; in fact, being away from her ex-husband meant that she was feeling attractive for the first time in more than 10 years. It was abundantly clear that this was done in fun – after all, she lived in the frozen north, barely two hours from the Canadian border and I was living it up in Austin. It became part of our friendship – a fun thing we shared as she started to get back into the dating market.
Then came the day that grad school nearly broke her.
It was becoming increasingly apparent that grad school was not for her – getting a doctorate in History almost ensured a life in academia and finding a tenure-track job at a university was akin to winning the Powerball. The sheer level of stress from the work and the vanishing future was taking it’s toll on her; she broke down in tears several times over the phone during our regular phone calls.
This was when I made my decision. We hadn’t seen each other in close to a decade; it was time that we fixed that. She was coming to stay with me in Austin and I wasn’t going to take “no” for an answer. She could stay in my spare room, I would cover food and entertainment. All she had to do was relax, decompress, down a margarita and enjoy herself for a couple of days.
I want to pause to emphasize that I had no agenda at this time. I was seeing a couple of girls on the semi-regular at this point. My only thought was taking care of my best friend who was having a difficult time at a tumultious stage in her life.
She thought about it for approximately 10 minutes before she said “yes”. She had some time off in a couple of months. This worked out perfectly, in fact; she’d be coming down just in time to celebrate my birthday with me.
This was where the real transition was beginning to start. I was slowly adding a sexual tinge to our friendship without bludgeoning it in and making things awkward. Flirting with women was a natural part of who I was. As a result, Cat felt comfortable with this new part of our friendship. Rather than trying to clumsily wedge a joking-but-not-really-if-you-say-yes “hurr, I’d like to fuck you” into things, I would make a comment like “stop it, you’re turning me on” that would make her laugh and we’d just continue on with our conversation.
More importantly, I was clearly flirting without intent, and Cat understood this. It was fun for the sake of fun that made her feel good about herself, but was nothing serious. I had no agenda in trying to get her into bed. If I’d been making a concerted effort in hitting on her or trying to get her to come down so we could bang, it would have awkward and uncomfortable.
It was this slow progression that made introducing the idea of sex more acceptable. Like the metaphorical frog in the boiling pot of water, the change was so slow and gradual that it was comfortable and natural, becoming the accepted state of things rather than a sudden and disorienting shock.
Equally important was that while I was willing to flirt with her, I still considered her my friendfirst. I might think of her in a “it’d be nice if…” kind of way, but when I invited her to visit me, I legitimately wanted to hang out with my best friend who I hadn’t seen in years.
The Break Out
As Cat’s visit loomed larger, I noticed that I had started thinking of her as more than just a friend. Our flirty back-and-forths was making me seriously consider whether it would be worth making a move or not while she was here. On the one hand, it wouldn’t be the first time I’d ever fucked my way out of the Friend Zone3 and I’d had enough friends-with-benefits to know I at least was capable of sleeping with a friend and not having things get awkward. On the other hand, she was going to be staying with me; the last thing I needed was to make her feel awkward – or worse, trapped – if it turned out that we weren’t on the same page.
I decided to proceed, but with caution. I planned out our time with precision, starting with my Standard First Date. We were going to start at my house; I’d give her time to change and freshen up, give her the tour (with a lingering moment in the back yard; the view of downtown from my deck has been the key to many a seduction in my time), then head for downtown. A stop at a bar where a band I knew was playing, followed by dinner nearby, drinks and dessert at a wine bar I knew well and then… well, who knows. I decided that I was going to be on high-alert; if I got any signals at all that she was uncomfortable, I’d ratchet everything back to “good friends having a good time” and that would be that.
The day she arrived, I was ready. The change in my behavior and personality had been one thing… but in the nearly ten years since we’d last seen each other, I’d undergone a profound physical transformation as well. I lost 40lbs of fat and started weight-training, completely altering my frame and sillouette. I’d learned how to dress well – no more Three Wolf Moon tees for me! – and how to carry myself with confidence. I was dressed to kill when I met her at the airport – a well-fitted black button-down, dark blue jeans, rockstar boots, hair impeccably styled… I looked awesome.
And it paid off in spades. She was shocked to a standstill when she saw me, actually pausing for a second to make sure it was me before she rushed in for a big hug. I picked her up, gently put her back on her feet, grabbed her bag and escorted her to my car.
“So we have plans for tonight,” I said when we got in. “… but I’m not going to tell you what they are. The only thing you need is your ID, so dress to kill and wear cute shoes.” She arched her eyebrow at me, but grinned. “Look at you, Mr. In Charge,” she said. “A girl could get suspicious.”
After a brief snack of pretzels and mini Bon-Bels, we hit the entertainment district. I took her hand as we walked down the street,pointing out local landmarks to her – places where various rock legends had gotten their start, clubs from my stories, the corner where the drunk girl tried to steal my boots. We both had a laugh when a drunk cat-called her, telling her that she was “too much car for me”. I yelled back that someone was going to be hugging those curves later and she gave me an elbow to the ribs before squeezing my hand and grinning at me.
At the bar, I held the door for her, my hand on her lower-back as I lead her to the bar. It was one of my regular hang-outs, so I paused to talk to people and bartenders I knew, introducing her as my oldest friend. She was having the time of her life, meeting new people and dancing to the band.
During a break, I returned from the bar with drinks to find a guy looming over her; he cornered her against the wall, leaning in and ignoring her increasingly unsubtle “GO AWAY NOW” signs.
I ducked under his outstretched arm and handed Cat her drink. I turned back to the guy. “Hey don’t be rude!” I said. “Introduce yourself.”
“I’m #######” he said. I could barely hear him; he was clearly annoyed that I’d wandered into what he saw as “his” territory, and was wondering what it was going to take to make me leave.
“Nice to meet you. Bye!” I said, turning my back to him, effectively cutting him out of the conversation.
Cat and I made small-talk as he kept trying to get around me. Eventually he gave up and stomped off in frustration. “My hero,” Cat said with a laugh.
“Hey, I had to drive him off,” I said. “Couldn’t have him hanging around when I did this…”
And then I leaned in and kissed her.
Cat stiffened momentarily with surprise, then almost immediately melted into me. When we finally came up for air – it felt like hours, but was only a few minutes – she took a deep breath. “Just how long have you been waiting to do that?” she asked, fingering the button holes on my shirt. “About…” I looked at my watch. “two hours?” I was joking, but only just. I was holding back slightly, gauging her reaction. She seemed pretty into it at the time but…
“Well, you’d better not wait that long for the next one,” she said.
I took the hint.
The changes in my personality that she knew about were one thing – it helped change her mental picture of me to someone who was sexual, but possibly not someone she could see herself with. The changes in how I looked – a night-and-day difference from the years she had known me in college – blew apart her mental image of me. My transformation had effected what I call The Cosmic Reset Button – I was someone she knew, but I was so different from who I’d used to be that she was forced to consider me in a new light.
Over the course of the evening, I was letting her know in little ways that I was interested in her as a man is interested in a woman rather than just as friends. I wasn’t treating her like a friend, I was treating her like a potential lover – the flirting in the car, taking her hand, guiding her at the bar with my hand to the lower back… these were all ways of building sexual tension without making it uncomfortable. It let things build, but without feeling forced; if I’d been more overt at the time, it would have made things awkward – after all, she was staying at my house. The last thing I needed was for her to feel unsafe or that I expected her to put out. Since she kept responding positively – flirting back, squeezing my hand, allowing me to lead her around the room with my hand to the small of her back – I felt comfortable in making my move.
When I did kiss her, I didn’t hesitate. I didn’t wait for “the perfect moment”. I made my move with the full expectation that she would welcome it. The fact that she leaned into me let me know she was at least physically into me… although while her body might be up for it, her mind might have had other ideas. Hence the joke about how long I’d been waiting – by making a joke, I was diffusing any tension about whether things would get awkward; if I could make fun of it, then clearly I wasn’t going to be butt-hurt about things if she decided she wasn’t in the mood. We could laugh about the moment and go about our time without her worrying that I was going to be upset or sulky.
As it was… it was perfect.
We didn’t sleep together that night. I didn’t push for it and while Cat was clearly happy that we’d taken our relationship to a new and exciting level, she didn’t want to rush straight into bed either. In fact, we didn’t sleep together until four days later, a night before she was leaving to head back home. While we had a hard time keeping our hands off one another whenever we were alone, we didn’t call attention to what was going on; instead of wondering at the fact that we were making out, we treated it as normal. I showed her around town, took her to all my favorite spots… and as soon as we got home, we’d make out on the couch for hours.
We were making plans for her next visit before she even left.
After she had arrived home, we had a long “what does this all mean” conversation; after all, we lived thousands of miles apart. We agreed that we were both on the same page – that this was a casual thing, no strings. We’d hook up whenever one of us was in town, but there were no expectations of commitment. We were just friends who’d fuck on occasion.
Eight months later, Cat quit grad school, got her masters and moved to Austin.
Our wedding was on Free Comic Book Day last year.
And it’s been an amazing adventure ever since.
- Seeing as my idea of romance at the time was based around having watched all the wrong movies and read all the wrong books [↩]
- Between her experiences and several friends’, I don’t know if I would wish a post-graduate education on my worst enemy… especially one that ended in a job in academia. [↩]
- Side note: guys, when you do get out of the friend zone, your cock starts to play the Jurassic Park theme. Just FYI [↩]