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Over a span of 12 years, Jessica Griffith has had seven boyfriends and one broken engagement. With those stats, I was surprised to learn that she’s a fairly cautious dater.

It makes sense, though. Her family has a less-than-ideal reputation when it comes to relationships. “Most of my family has been divorced. My maternal grandfather is on his seventh marriage, to give you a gauge of what passes for normal in my family.”

So, after things fizzled with her then-fiancé—“Neither of us knew what we wanted”—she lived the single life for around six years. The first year was spent finding herself through weight loss, performing musical theater, and finishing college.

Once she was ready, she decided to try online dating.

But, between “aggressive dickpic barrages” and people who ghosted once they realized she wasn’t looking to just hook up, few dates really panned out. “When you’re single for a long time, it takes more and more to persuade you to try again.”

Trying out so many different dating apps and sites had a negative effect on her self-esteem. Like so many virtual interactions, it seemed like men forgot they were talking to an actual human. “People say whatever they think of you.”

She has to admit, though, that she wouldn’t tell people to avoid online dating. After all, she met her current fiancé, Riley, on OkCupid. He got her attention by sending her daily puns and being the first guy to treat her like an actual person.

Still, Jessica didn’t want to get her hopes up.

At that point, she was positive she just wanted to be single forever. But more than that, she was nervous about one big detail: Riley is trans. Throughout her life, she hadn’t known many trans people, much less dated a trans man, so she had an “uneducated belief that going on a date with him would be like going on a date with a woman” (which she’d done).

All in all, when she walked into the pub where they were meeting, she felt apprehensive, at best.

Quickly, her hesitation turned into joy. “I felt incredibly relaxed and comfortable around [Riley]. We talked and shared fries and laughed. A lot.” From that one night in August 2017, their relationship moved on an accelerated timeline.

By mid-October, they were living together and had already started talking about maybe getting married.

Unsurprisingly, their families were a little concerned about how fast they were moving—Riley’s especially.

Early in their courtship, Riley’s sister went through a devastating break-up with her fiancé, who had been around for years. Feeling betrayed, Riley’s family was extremely “gun shy” about Jessica. When he started talking about wanting to marry her, they expressed concerns that he wasn’t acting like himself. Jessica doesn’t blame them; they just wanted to make sure Riley wouldn’t end up in the same situation as his sister.

To ease their minds, Jessica and Riley have had a long engagement.

By the time they get married, this February, they’ll have been engaged for a little over a year, and together for about a year and a half.

Jessica admitted that their whirlwind romance is a little crazy. “Everyone thinks we’re nuts. We think we’re nuts. But we’re also really happy.”

What she loves about Riley is the fact that she can trust him. Before, she’d never felt comfortable relying on people, and it wasn’t until they started dating that she realized it’s okay to ask for help sometimes. When she let her teaching job eat away at her physical and mental health, it was Riley who told her that she needed to put herself first.

In addition to calling her out when she’s holding herself to “impossible standards,” Riley is the first person Jessica’s dated who actually respects her. “I don’t think anyone I dated in the past really respected me as a person. I think a lot of them wanted something from me and saw our relationship as an exchange of services.”

When I asked about society’s view of her relationship, she said that they haven’t met much scrutiny. Unless Riley brings it up, few people—other than his family, close friends, and coworkers—know that he’s trans. While they worry about potentially having a hard time adopting when they’re ready for kids, Jessica’s main frustration is dealing with people who expect her to fix their ignorance. “Society seems to think it’s my job to educate them about my relationship and prove it’s ‘okay.’”

This isn’t to say Jessica doesn’t face any discrimination.

When she and Riley got engaged, her friends weren’t over the moon about it. “A lot of people probably think that since we got serious so quickly, we won’t last.” Now that she’s left her job, making Riley the financial support of their household, she’s heard a lot of snarky comments about how nice it must be to be a housewife. (The sting of those remarks has even kept her from changing her work status on Facebook.)

What’s more, being an overweight woman, she’s certainly felt unsafe in the past. Still, being with Riley is the first time she’s feared how federal law could negatively impact one of her relationships.

But, through all the drama and judgment and worry, Jessica knows that Riley is the person with whom she wants to spend her life. Their life goals align perfectly, and he’s always gone out of his way to prove that she’s on his mind, like how he’d bring her snacks when she stayed late at work. They take care of each other, and that’s really all one can ask for.

“Just knowing there is a lifetime of more moments ahead is exciting.”

N. Alysha Lewis

N. Alysha Lewis is an editor and blogger with author aspirations whose love can absolutely be bought with french fries.

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