If you’re over thirty and single, it’s likely not because you’ve never had a special romantic connection, but rather that the connections you’ve had miscarried for one reason or another. The fallout from such a miscarriage can be a complicated space to maneuver.

Scenario: You Walked Down that Road, but it Didn’t Work Out

Single at this point in our lives, we’ve all visited this scenario, yes?

When David and I found each other, I thought my days of searching were behind me, that I was done collecting stamps in my passport and had finally arrived at my destination. He said, “I’ve been looking for you so long,” and “I never want you farther than an arm’s length away,” and “I want you here with me in Santa Fe.” He made me feel like THE woman. And yet, as you may infer from the heading, it didn’t work out.

Some part of David panicked about commitment. He came back a few times, but, inevitably, he always panicked and disappeared. At some point, he asked if we could be friends. I couldn’t do it. I wasn’t going to be just another ex-girlfriend who’d shifted into the “friend” category. That would’ve devalued the power of our connection. And frankly, I couldn’t emotionally handle being “friends” with a man I loved so deeply. As emotionally difficult it was, it was easier to extricate him from my life altogether.

Damon and I only had two dates, but with long distance, you don’t bother going on a second date unless there’s some compelling chemistry on the first. And though there wasn’t a third date (his call, not mine), he played peekaboo with my Match profile for several months after our second date, looking silently but not actively engaging with me. He clearly liked me, but also had reservations.

A little over a year after our second date, Damon finally stopped playing peekaboo At that point, it was a relief. As long as he played peekaboo, it kept the flame of little-h hope alive, a wistful place to live. When he finally disappeared, it made it easier to face the reality that We weren’t going to happen.

With both David and Damon, if We weren’t going to work as a couple, it was emotionally easier to not interact with them at all.

Yet with Stanley, who I dated for four years, I’ve managed stay amicably connected. Why can I manage maintaining contact with him versus David and Damon? Perhaps with Stanley, it’s as simple as I’m the one who called our relationship off, so I’d already made peace with no longer being an Us. On his end, I think he initially held out hope we’d reconcile. Now, he’s remarried, so that hope’s in the rearview mirror, yet he still seems able to comfortably interact with me without the hope or expectation that we’ll ever be more than we currently are.

With some men who I’ve been romantically involved with, I’m able to handle maneuvering the tricky space of our post-romantic connection and with others, I can’t. Likewise, I’ve had men that post-romance couldn’t handle maneuvering that space with me. And that’s fine. It’s a tricky space to maneuver.

When faced with these tricky spaces, we each need to find what we can handle; what we’re comfortable with; and what, within reason, we want to, and are willing to, make of that space. Most importantly, how can we make that space an emotionally healthy place to inhabit? If we can’t, we may need to abandon that space altogether.

Scenario: The Chemistry is Strong but Relationship Doesn’t Manifest

This is a scenario that I’ve recently been struggling with in my own life.

I became acquainted with Evan over a year ago. He lives in Florida and, from the beginning, made clear that he didn’t see a long distance relationship “in the stars” for him. Despite that, he was taken enough with my Match profile that he felt compelled to get to know me. Our first phone conversation lasted four and a half hours. The words between us flowed easily. He said that we’re “kindred spirits.” We clicked.

On my end, I found (and continue to find) Evan attractive on many fronts–he’s tall and good-looking; he’s stimulating conversation; he’s compassionate and considerate; he’s successful and ambitious; he comes with a great (British) accent, and he’s the one of the funniest people I know. He makes me laugh. He makes me feel appreciated. He makes me feel cared for. He’s the kind of man I seek as a life partner. And while I’m grateful for our connection, it’s always been bittersweet for me–the sweetness of our connection coupled with the bitterness of the limits he’s imposed upon it.

Of late, as sweet as Evan is, the flavor I’m left with is bitter. The feelings have become too hard. Why now? It’s complicated.

Perhaps it’s because the flirting’s taken a heavier turn than it has in a long time, stirring up my emotions and desire–something I can’t afford to do when the signage on the road to him reads “Dead End.”

Or maybe, as a “friend” with chemistry, I’ve surpassed my threshold of tolerance for hearing about the women he’s dating.

Maybe it’s that he’s recently mentioned dating possibilities with women out-of-state, but retains his no-long-distance limits with me, suddenly making his lifestyle choice seems more like a personal rejection. At this point in my life, that doesn’t sit well with me.

And frankly, the juxtaposition of hearing about other women; having limits enforced on our relationship; yet simultaneously being sexually enticed is, well, emotionally discombobulating.

In all of this, of course, I recognize feelings of jealousy, and I don’t like feeling that way. I want Evan to be happy, but right now, I’m unable to bear witness to that happiness regarding other women. It’s a tricky emotional space to maneuver. Too tricky for me right now.

So, what to do when you’re feeling tricky emotions? Create emotional distance as you’re able and set boundaries to take care of yourself.

For me, that means that I need to step back from our relationship for now. I need to take some time away from him to allow my emotions to calm. And as long as there’s “Dead End” signage for me on the road to him, I need to set my own boundaries (i.e., no heavy flirting) to be able to comfortably live with his limits. I need to find new ways to maneuver in this relationship, because The Way We Were isn’t working for me anymore. Our relationship isn’t just on his terms, but also on mine.

And yet, conversely, there’s Isaac. He’s been in my life for over a decade now. Our chemistry and connection are strong, yet it also come with limits. Isaac’s limits. With time, I’ve learned to negotiate those limits in a way that I’m struggling to with Evan right now. I can indulge the heavy flirting with Isaac in a way I’m currently unable to with Evan.

What’s the difference? Time, perhaps. Or maybe different relationship histories and origin stories. But ultimately, each relationship has its own unique dynamic and what works to maneuver one connection successfully might not work for another and might not work consistently across time. Find your comfort zone for each unique connection and across time.

Scenario: The Interest is One-Sided

In this scenario, there’s an imbalance in the level of interest. One person has romantic feelings that aren’t reciprocated–the “unrequited love” of literature. But if it’s not requited, is it really love or simply a crush?

With Pierre, while I was intrigued enough to get to know him, I soon realized I didn’t feel the chemistry of romance. When I expressed this to him, he wanted to stay in touch, to “be friends.” We continued to talk for a while, but he began to push at the limits I set, as if I could be convinced to have feelings for him. When he was unable to accept my limits without trying to push beyond, I had to go from being friendly to curt, in order to make my point.

I met Keith walking on the trail near my house. Our acquaintance began as simply a smile of recognition. One day, he broke the ice and we started talking. Eventually, we become walking buddies. I liked Keith, but never felt any romantic chemistry with him. One day, he asked if he could kiss me. Politely, I declined. I valued our connection, but desired nothing more than friendship with him. He accepted that, and we remained friends. He’s now married to someone who suits him much better than I ever could have.

In the case of men who I don’t feel romantic chemistry with, I’m careful not to flirt with them whatsoever, for if you don’t have romantic inclinations for someone, it’s unfair and unkind to flirt and lead them on. To flirt where you lack intention or desire is about ego and game-playing. We’re not in high school anymore, and we should be beyond such behavior.

Maneuvering

This past summer, I went on a date with a birder. From him, I learned many interesting things about birds, including that birds who live in forests tend to have long tail feathers for quick and precise maneuvering among the trees. Birds who live in open spaces tend to have shorter tails, as they have no need for such maneuvering. This strikes me as a good analogy for different kinds of relationships.

Our easier, more straightforward relationships are the open spaces where we can soar and freely explore the expanses. No deft maneuvering required, no “Dead End” signs.

The forest is full of trees to maneuver around, obstacles to straightforward flight. Obstacles are the limits and complications in our relationships, the tricky bits. It takes skill to maneuver in these spaces, sometimes more skill than we may possess.

In maneuvering your complicated relationships, the key is being respectful of others whilst also taking care of yourself, whether you’re establishing limits for yourself, abiding by someone else’s limits, or working within the limits of the situation.

Considerations for maneuvering your complicated relationships include: the value of the person/relationship to you; what limits you’re comfortable with; what limits you may need; how you feel; whether or not any emotional discomfort is manageable (and worth the discomfort); whether you feel able to maneuver the tricky spaces; and if you need to create emotional distance or potentially remove yourself from the relationship altogether.

Scenario: You’re In a Relationship

When you’re in a committed relationship, that person should be the priority, and it’s your job to ensure that they feel they are. To that end, consider whether you need to put additional limits on any complicated relationships that you have. If the person you’re in relationship with feels justifiably threatened or jealous, you risk the relationship and losing your person.

For me, that means that when I’m in a committed relationship, I establish boundaries on any flirtatious activity outside of that relationship, such as with Isaac. I don’t sever the connection, nor do I go silent, I simply pull back from flirtation. When in a relationship, I save the flirtation for the man who offers me expanses, not the one who imposes limits.

Final Thoughts

There are many scenarios that can make a relationship complicated and tricky to maneuver, and each relationship dynamic is unique. Find your comfort zone where you can remain emotionally healthy within each of your complicated relationships, and remember that what that comfort zone is may change with time.

Take care of yourself and good luck maneuvering out there!

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