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#108 Millennial Meg Ryan
If you’ve been wondering if I’m still hooking up with Goodtime Guy, the answer is yes. We see each other about twice a month, and the sex has only gotten better. :) I’m also delighted to report that feelings are nowhere to be found! Which is interesting because I think we are becoming friends? We obviously get together with the main intention of fucking, but the hanging out before and after—whether it’s a post-coital meal or a pre-coital night out (neither of which are dates)—is also quite nice. He’s a lovely guy and I enjoy his company; he’s not just a piece of meat. We don’t talk much between dick appointments, but I truly don’t mind…
Because while consistent, delicious sex is great, so is laughing on the phone for 3 hours with a cute guy who lives across the country. :D
How did I meet someone who lives so far away?
The internet, of course! He and I both belong to an odd little Slack community of brand builders. We had briefly interacted once or twice, and then last Fall, we talked a bit more when he signed up for the professional development & networking program I’d been promoting. At the time, he happened to be in New York (visiting his girlfriend who had recently moved here), and asked if I wanted to meet up IRL. Some other Slack folks were having a party, to which I invited him (+ another person in the program) so we could all get to know each other better. It was a lovely evening of platonic networking, with the highlight being that I insisted he read The Artist’s Way. A few days later, our program assigned us to the same 7-person team, which meant he and I would see each other on a weekly Zoom call for the next month and a half. However, he was MIA from the last few meetings, and I occasionally wondered what happened to him.
Ok, so how did he go from semi-professional-acquaintance to person-of-romantic-interest?
In January, when I finally remembered that I’d been wanting to check in with him, I messaged him on Slack to ask how he’d been. He told me he was taking a break from work and reading/loving The Artist’s Way. He asked how my writing was going, specifically my dating newsletter (which I had told our team about). I added him to this email list, shared the archive with him, and he immediately started reading my latest posts. When I realized he was reading the posts in reverse chronological order, I told him he should start from #1 in order for it to make sense.
The following is paraphrased from memory because our Slack runs on the free, messages-disappear-after-a-few-days plan:
Him: Uh oh, did I just spoil the whole thing for myself?
Me: haha spoiler alert: I’m still single!
Him: Hey, I’m single now too!
I knew he’d been with his girlfriend for like 5 years so I was VERY surprised to read this. As a single woman ravenous for any morsel of male affection, it’s always exciting to hear about a new man on the market—even if that market is based in Seattle. I’d be lying if I said I wasn’t intrigued, but I figured this just meant we could become friends without worrying about stepping on any girlfriend toes.
Anyways! Once he was informed of the proper reading experience, he proceeded to spend the next two nights reading ALL 107 ENTRIES—messaging me his favorite excerpts along the way. Needless to say, my ego was wet. After Slack-ing some more about my emails, Julia Cameron, and strawbale houses, I gave him my number and told him to give me a call so we could swap Artist Date ideas. I can honestly say that my intentions at this point were 98% platonic. I knew he lived far away, but he seemed to be a likeminded weirdo and I was excited at the prospect of becoming Real Friends.
He finally got around to texting me about a week later:
Him: In this rapidly advancing digital age when you say ‘give me a call’ do you wanna actually talk on the phone or video call?
Me: While I have nothing against seeing your lovely face, I’ve grown nostalgic for old fashioned telephone calls (I’m even buying a rotary phone as I’ve finally figured out how I can route my cell phone calls through one)
Him: Sounds like you should call me on my landline phone for our very vintage phone chat
He shared a photo of his WOODEN NOVELTY BOAT PHONE, and the rest is history. After I quickly died and came back to life, we scheduled our phone call for the following week. I assumed an hour would be plenty of time, but we ended up talking for TWO. Our second phone call? THREE hours long.
We talked about all sorts of things: movies, solitaire, his Saturn Return, quitting the rat race to become artists, the tactile ecstasy of fingering an analog phone or cassette deck—y’know, normal stuff. “Rotary Boo” (coined by my cousin) was sooo funny, smart, and interesting; and I was quickly obsessed.
For two whole months, we were talking on the phone almost-weekly, and—despite agreeing that it’s the lowest, albeit most convenient, form of communication—texting almost-daily. That added up to 9 phone calls, ranging anywhere from 90 minutes to 4 HOURS. We had also swapped addresses after our first call so that we could send each other mail. I sent him a postcard and he mailed me *physical* photographs of a strawbale house tour he took. When he broke his knee in late February, I surprised him with a box of Thin Mints.
I realized I had a Full On Crush™ on February 11th. I was having some coupled friends over for wine & cheese & laughs, and I noticed how much I wished Rotary Boo could have been there as my plus one. That’s also when I realized that I probably needed to tell him how I felt.
Having been unheard-of-ly transparent with him thus far (e.g., he had already explored the cringiest corners of my life & brain—aka this newsletter—so I didn’t think twice about disclosing things like my love of astrology or homemade deodorant), I felt it would be dishonest of me to continue hiding my feelings. For example, during one of our (consensual) astrology chats, he had asked what the planets said about our compatibility. I didn’t know if he like-liked me, too, so I reflexively dodged the vulnerability ball and stammered out: “uh… we vibe.” After all, he was still fresh out of a long-term relationship (“recently-divorced” as I like to say) and I didn’t want to freak him out with how “powerful” The Pattern says our romantic bond is. Truthfully, I had basically been playing it cool ever since our second call, when he revealed that he’s a Cancer(!).
During the first three weeks of sustained communication with Rotary Boo, I didn’t hear from Goodtime Guy and assumed he’d lost interest. But on February 13th, I woke up to this late-night poetry:
“Hi, so when can I go down on you?”
I had only just acknowledged my Rotary Boo crush, but there was no way I was turning down this offer. So, I met up with Goodtime Guy later that night. :D
~~END OF INTERMISSION~~
The next day, Valentine’s Day, I worked up the courage to inform Rotary Boo of my crush via a Google Duo video message. While we had never communicated via this medium, I assumed he had the app because he’s an Android user. *Shrug* To this day, I still don’t know if he’s ever seen that message lol; he’s never mentioned it, and I’ve never asked him about it. Regardless, I was proud of myself for bravely professing my feelings—even if they did disappear into the ether. It was a baby step down Vulnerability Road!
As Rotary Boo and I continued to talk, and my crush continued to grow, (and I continued to hook up with Goodtime Guy…), I would go back and forth on whether or not I should tell him about:
My more-than-friend feelings for him, and/or
The sexual relationship I was having with someone else!
As you all know, this was uncharted territory for me. I was having sex and catching feelings—with two different people! While I didn’t want to lie or withhold from Rotary Boo, I also wasn’t sure if my sex life was any of his business, considering the fact that he had yet to express any explicit* romantic interest. As for Goodtime Guy, I knew he wouldn’t care at all about who I was talking to on the phone. So, as I gradually got my sea legs on the ocean of ambiguity, I figured there was no harm in continuing to have a physical relationship with Goodtime Guy while having an emotional relationship (at least on my end) with Rotary Boo. I didn’t owe either of them anything more than I was giving, and I was trying to stay focused on my joy and pleasure.
*While I love to wildly speculate, I hate to jump to conclusions. Yes, Rotary Boo once left me an insanely cute, just-thinking-of-you voice memo telling me to watch Drive My Car—saying that 3 hours had never passed so fast, with the exception of our phone calls(!!). Sure, he once wondered aloud (via text) what his ABCDEFG name would be. And duuuuh, he was spending hours on the phone with me almost every week. But unless I have *irrefutable* proof that someone likes me, I can never assume we are anything more than good friends.
So there I was, starring in my very own rom-com! It was kind of amazing. I suspected there could eventually be an everything-blows-up-in-her-face-and-she-ends-up-alone scene… but I’d cross that bridge later. For now, I was reveling in getting allllll my needs met.
At the beginning of March, having recently returned from a warm & tropical yoga retreat to the cold & colorless hell that is late-winter NYC, I decided it was time to start exploring in earnest my options for a West Coast move. Seeing that I now had a friend in Seattle, along with family and friends in Portland, I booked a PNW trip for the end of April / beginning of May. With these plans confirmed, I concluded that it no longer made sense to tell Rotary Boo I had a crush on him before hanging out in person—just in case there was no romantic vibe and we actually were Just Friends. All that hemming & hawing paid off and I continued to harbor my secret [read: probably-super-obvious-to-him?] crush for the next 2 months.
Around this time, Rotary Boo and I noticed that some of our texts had been getting lost. We relocated to WhatsApp, but wondered if this was the Universe telling us to finally fulfill our 20th-century fantasy and give up texting for good. I suggested we challenge ourselves to only talk via phone calls and snail mail during “Analog April” and he enthusiastically agreed.
It was a cute idea in theory. In practice, Analog April was a bit of a letdown lol. We went from talking almost every day to… barely talking at all. I played it cool for an entire day before leaving him a voicemail on April 2nd. I left another message on April 4th. By April 6th, there were also 2 pieces of mail en route to him, and I hadn’t heard a PEEP. I remember thinking, “If I knew we just wouldn’t talk anymore, I never would have suggested Analog April!” That night, as I was getting ready to go see Goodtime Guy [read: trimming my pubes over the toilet], my phone rang. Of course it was Rotary Boo. Naked and surprised (and running late), I let it go to voicemail. He said he had been super busy with work and asked if I’d received anything in the mail. The next day, I indeed received his postcard (postmarked March 28, which I appreciated) and called him up for a typical 2-hour chat. At the end of that call, we planned to talk again on April 12th. We also “briefly” chatted (for 48 mins) on April 9th when I had to ask him a question that would normally be a text.
He was going to be traveling for the second half of April, so those 3 calls concluded our communication for the month. I ended up sending him a total of 4 pieces of mail, including a short letter saying how much I appreciated our friendship—which I knew he wouldn’t receive until he returned to Seattle on May 4th, the same day I would arrive. (In case you’re keeping score, he sent me 2 pieces of mail—one of which was lost and never recovered. :’( While I’m still dying to know what was in that envelope, I do not resent him—or anyone, for that matter—for not matching my postal output. I am a mail queen!)
After three weeks of total, albeit planned-for, silence, I didn’t hesitate to text him as soon as May arrived. Things seemed normal. I was in Portland (having a very good time, btw) and would be taking the train up to Seattle in a few days. I was looking forward to finding out, a) if I liked Seattle and, b) if we liked each other. Having only briefly met once before, under very different circumstances, I was anxious!
What if he didn’t like me?
What if I didn’t like him?
What if the past 3.5 months had been for nothing and I’d have to start over from scratch with someone new??
May 4th - PDX → SEA (irrelevant texts omitted)
Rotary Boo: hey when do you get into Seattle
Me: I’m on the train now! Getting in at 3:30. You?
(2 hours later)
RB: So I bump bump bumped my flight up cause my buddies all left early and I get in at like 530 I think
(1 hour later)
Me: Welllll let me know whenever you want to hang out! (Doesn’t have to be today) I’ll just be wandering
(1 hour later)
RB: Yo yo! Got home a little bit ago took a shower and ready to party. Where you at! I can come pick you up and take you to this sweet park