“Homesteading” isn’t a term we hear often in contemporary vernacular, but it’s exactly how M Shelly Conner and wife Tiffany Conner describe life on the 15 acres they share with their two-year-old dog Whiskey in central Arkansas. It’s a long way from Chicago, where the couple first met in person in 2016 after connecting on OKCupid.
“I was impressed with her profile,” Shelly, a writer and professor, recalls. “We’re both bourbon aficionados and she wrote that her favorite food was Brussels sprouts which I had really started to enjoy cooking at the time. By the time we moved off of the dating platform, we had given ourselves the nicknames Pink Whiskey (Tiffany) and Bourbon Girl (Shelly).”
“On the dating app, Shelly was witty and intelligent,” adds Tiffany, who manages Human Resources Information Systems (HRIS) for an architecture and design firm. “I liked her confidence. I was pleased that we were the same height—I like them tall!”
The two began their courtship writing and texting. “She was very charming and I was excited but nervous to move to the phone,” Tiffany admits. “But when we finally did video chat it was pretty effortless.”
“I thought that she was incredibly quick-witted...funnier than me. I’m used to being the funny one!” Shelly adds. “[Tiffany] just has this glow that draws people right in...even to this day. People are drawn to her. She’s really quite brilliant in so many respects.”
A month into the relationship, their shared love of bourbon led to declarations of love for each other, as the couple prepared to take our first road trip together to the Kentucky bourbon trail.
“I had written [Tiffany] a letter declaring that I was ‘falling in love with her’,” Shelly explains. “[I] wanted to surprise her with it so I mailed it through postal mail from the drop box in her building. I wanted it to arrive before our departure. But days passed and it never arrived! The day of our departure, it showed up at my home—the return address—marked undeliverable. So I just ended up hand-delivering it to her.”
For Tiffany, “the ease of planning travel together” and their first night on the road sealed the deal. “We started hashtagging our travel as the #AdventureofPinkWhiskeyandBourbonGirl,” she says, adding. “Everything from the beginning and even now is really just effortless with us.”
The two credit empathy, therapy and communication with their success as a couple, including extensive and honest early discussions about the challenges faced in previous relationships, in hopes of avoiding the same mistakes. “But things were notably different for both of us starting with ourselves,” they tell The Root via email. “We had both done the post-relationship self-work required to be ready to enter a new relationship and not allow past issues and ineffective ways of dealing with them to handicap it.
“It starts from within. You have to do the self-work,” they further explain. “You cannot ask for trust that you are unable to give. Too often people have these lists, which can be helpful to identify what you want. But they aren’t very realistic and don’t always delve into what you need. If you cannot be honest with yourself, then you won’t be honest with another.”
“I think that we’re really good about talking things out,” Tiffany offers. “We do equally hate to be mad at one other. It kills us both.”
“Which makes it easier to either apologize or speak openly about what is bothering us,” Shelly adds. “It helps to do it early. Sometimes, it’s even saying, ‘Something’s bothering me. Don’t know what it is yet but I’m feeling anxious/irritable/etc.’ Then most times, we can tackle it together.”
In fact, they agree that their greatest challenges have been the things outside of our relationship: “Life. Losing parents, pets, unemployment, relocation. Things that we’ve seen add pressures on people and therefore on the relationship. So although these things were challenging, they were not challenges to our relationship,” they write. “We viewed every single one through the lens of us as a unit. Not as Shelly is unemployed or Tiffany doesn’t have a car, but as we are searching for a position for Shelly and we have one vehicle.”
In 2017, Tiffany proposed, amid “an emotionally exhausting year” that included the death of Shelly’s father, managing his arrangements and making extensive repairs on Shelly’s home Chicago in preparation for a relocation to Arkansas after she secured a university position. “And we were filming my [web series] Quare Life at the house as well,” Shelly adds. “Every weekend was packed with something and the first one that we had to ourselves was the weekend of June 10.
“It was still a bit chilly in Chicago during the morning and Tiffany suggested we make brunch and asked me to start a fire in the backyard fire pit. When I got it started, she came out and said that she had a little present for me and she presented me with a photo album,” she continues. “It was a chronological documentation of our entire relationship until the very moment including some of our original OKCupid correspondence, a picture from our first date at C2E2 (Chicago’s Comic-Con), hotel key cards from our travels, and printed text messages. The final page turn asked, “Will you marry me?”
“When I looked up from the album, Tiffany was standing there with a quivering lip and a ring,” Shelly concludes. “I, of course, said yes!”
To ensure they’d have full rights as a married couple once in Arkansas, the two privately married ahead of their relocation in February 2018 at the Chicago courthouse. A larger ceremony took place in September of that year at an all-inclusive resort in Cancun, Mexico with 92 guests in attendance, a celebration that “combined our favorite people enjoying vacation with us in paradise while also witnessing our union,” the couple says.
When asked to share their favorite qualities about each other, the two are effusive. “Tiffany is extremely thoughtful,” says Shelly. “She remembers birthdays and important things, not just for me, but [for] everyone that she cares about and loves.”
“I have always admired how Shelly sets her mind to something and makes it happen,” says Tiffany. “I’m always in awe of how she talks about something happening and focuses until it happens. I’m a little jealous of it too. When her mind is set on something, she does it.”
To that end, Shelly is now also a published author; her debut, Everyman: A Novel, hits bookstores July 20. She and Tiffany are also working on a screenplay together.
“I’ve wanted my novel to do well because it’s been my life’s work and I have suffered through underemployment and so many things in bringing it to life,” she says. “Now that my life is also with Tiffany, I want that book to provide us with freedom.”
That freedom will hopefully include “so many things!” Tiffany exclaims. “Developing our homestead. Traveling the world. Raising children. Selling our screenplay.”
If that sounds like a lot of togetherness, “It should go without saying that you should LIKE your partner,” the couple writes. “Like to spend time with them. Like to share activities and events with them. You really should be if not, the best of friends, certainly very close ones. But also it’s great to have separate friends and activities and hobbies as well. Some that you introduce to each other, some that you find together, and some that you respect as being separate.
“Real love recognizes that dating never ends,” they add. “You continue to maintain and improve the acts that got you in the relationship. Real love knows that something that may not be important to you but is important to your partner should be easier for you to do—cause it’s such a small thing for you but means the world to your partner.”
Clearly, it’s a commitment to growth that’s working well for the Conners.
“[Our relationship has] definitely gotten stronger in all aspects. There’s more of an emotional connection and deeper understanding of who we each are,” says Tiffany. “What’s made us stronger is our shared vision for the future and our equal excitement and passion for our lives. We continue to be supportive of each other...But we have never had a tumultuous, rollercoaster up-and-down story. What’s a rollercoaster that only goes up? An elevator?”
“Those also go down, love,” Shelly chimes in.
“Well an UP escalator!” Tiffany responds.
“I agree. It started very strong and has only grown in all aspects,” Shelly adds. “We started with trust, but even still, sometimes old insecurities rear up and you think, “does this person really mean this?” But Tiffany shows up for me every time and I am determined that I do the same. This is the love that I asked for and I worked on myself for and I am constantly making sure that I continue to be the person who deserves it.”
You can read prior installments of “How We Do” here.