How Long Should You Wait Between Relationships?

We’ve all seen those people who move from relationship to relationship, some of which are extremely long term, without so much as a couple of weeks in between. We wonder what’s going on with them and why they can’t stop. Maybe as you’re reading this you’re one of those people. It’s okay, well it’s not, but we’ll get to that in a minute. What I mean is, there is still hope and you’ll find that taking time between relationships can help you be better equipped to achieve what you really want in life. 

Once upon a time, in a galaxy a couple of miles away I went out with a woman a few times during which she was chastising a previous date who turned her down. His reason was that he had told her she wasn’t ready to date yet. She felt that was patronizing and a bit patriarchal. I get that. However, I’m guessing what he was saying, perhaps poorly, was that she was still carrying around too much unresolved pain to begin a relationship from a place of strength. He didn’t want to be the partner who was chosen because of her insecurities. 

I actually agreed with him, I could also sense this tendency in her. She was still too upset about her recent divorce and the insecurity it left her with to be dating me or anyone else in a healthy way. 

Some people in this situation would date her, either because they are oblivious to what is happening, have their own insecurities, or because they have hope that things will work out. I wasn’t about to become a patch for her personal issues. Folks like her in this situation tend choose partners to make themselves feel better, not necessarily because they are a good match. Keep in mind it is possible that someone could still stumble onto a good match for the wrong reasons. It happens. Generally though, insecurity blinds us to who is truly a good match.

I want to say from the outset that I don’t know all of this from intuition. I know it because I have been down and dirty in the trenches of insecurity myself. I have made all the wrong choices in partner selection before. In the hopes that I can help you from making my mistakes, here are my stages of recovery for judging when I can enter a relationship again. Hopefully you find it instructive.

Stage One: I need it!

If you have an emotional urge to go on a date then it’s too soon. In this stage I guarantee you will find someone with whom to start a relationship. The partner you find is likely acting from a weakness as well. Folks that are emotionally aware and balanced do not generally choose folks who are in the midst of emotional turmoil because it feels unsteady and it takes them in a direction they do not want to be.

You are still too close to the trauma of either the breakup or your emotional insecurity to make wise choices about a partner. You are seeking to fill a void with someone else. It’s not really a void mind you, but that is what your subconscious is telling you. Really, it’s just our unwillingness to go through a little emotional work. We know that work will be unpleasant so instead we opt for pleasure and comfort in the form of a new partner.

In this state, even casual encounters (where hopefully each person knows it is casual) are troublesome, because there is too much of a tendency for people to want to settle back into a relationship. That person you found a few weeks or even a few months after your last relationship ended is probably not the person with whom you will be compatible. Too many one night encounters end up long term for all the wrong reasons. It is perfectly understandable as we are all just seeking comfort, but comfort at this point needs to come from within and not from without.

When this relationship ends, and they generally always do, you will find that you didn’t do any of the personal work that you needed and you are back to struggling with your insecurities. The kicker is you may find that these insecurities are even worse now having been magnified by another dissolved relationship. Shampoo, rinse, repeat.

In case it isn’t clear, this is the point where you should not be dating, it is where you should take some time and be single. Learn how to be content existing within yourself. Get used to the lack of communication from a significant other and focus on friendships and hobbies. Basically, just take time for you to get used to this new phase in life.

Stage Two: I could take or leave it.

This is where you feel like you could take or leave dating. This is actually a good place to be and it often feels like it is enough of a calm. However, I’m going to make the argument that you are not quite there yet.

I say this because this stage is generally where people try to date but get overwhelmed by some aspect of the dating experience. This is evidence that there are still some issues you need to work through.

Everyone has disappointing dates that wear on us and make us wonder if any date is going to work out. This is normal. What I’m talking about is more than that. This is when we get overwhelmed fairly early in the dating experience.

This is also the stage where I find I can still get hooked on someone before we even meet. Not always mind you, but if that happens then alarm bells should be going off.

Stage Three: Do I even want it?

The final stage is where you will wonder if you’ve gone too far the other way. When I start to question whether I want to date at all because I’ll have to change my routines and accommodate someone else then I know I am actually in a good place and now is the time to start swiping on those dating apps.

Many people envision this as having gone too far the other way but I couldn’t disagree more. You have found comfort in being single and now you are questioning changing that comfort for someone else. Accordingly, your comfort will only be amended for someone who is worth incorporating into your life. This is far better than the other stages where comfort is seen as coming from someone else.

In this emotional state I’m pretty even keel. No matter how many of my boxes someone checks off before we meet I rarely get excited. Even when I do, it’s still a state of being wide open to possibility but simultaneously aware that statistically there’s a better chance of things not working out. 

It’s just being at peace with the fact that you are going to meet far more people that you don’t click with than you do. If you’re falling for everyone you date then you are still back in stage one. 

This as you can imagine is the hardest place to reach and one that I fear many people have never experienced in their life.

My tip

If you have never done this before then expect to have some uncomfortable things revealed to you. There can be moments when this is difficult especially as one tries to move out of stage one. Knowing that you should wait but dealing with your emotions that tell you to throw your hat into the dating ring can feel horrible. It’s the realization that your brain is trying to self-sabotage. It might make you realize just how out of control you are and that ain’t a pretty sight. Believe me, I know.

Objections and caveats

Some people say that you can come to terms with your emotional state while dating. This is true. This is also what I am trying to help you avoid. That sounds weird doesn’t it?

Coming to terms with your emotional state while dating is what will likely end your poorly chosen relationship. You will realize that this person is not a good fit for you. The reason for that is you never achieved clarity between relationships. This guide is meant to help you choose better partners by not caving into your insecurity.

Plus the time is only going to do you favors in your next pairing. I guarantee when you find a partner who wants to be serious that they will appreciate the distance between your last important relationship and them. No one wants to enter a relationship with someone fresh out of their last one. We only do so, out of fear.

I should also say that this whole thesis depends on whether you are looking for a long term relationship. There are those folks who are not. I am not asserting that a committed relationship is the gold standard. It is however, what most people at least claim they are trying to achieve.

I also think this applies to polyamorous breakups even when a person is maintaining a relationship with other paramores. Heal from the loss of one partner and check any insecurities it creates before setting out to find another.

I’m also not suggesting that your emotional house be completely squared away. I’m not even sure this is possible. You don’t have to be perfect before you start dating, rather you should just make sure that you have done the emotional work so you are not acting from insecurity. Hopefully, this will help you better choose your next partner.

The Evolution of Gender

Gender is a complex and wonderful thing. Currently we are living in the golden age of gender. Folks now have a greater awareness and social acceptability for more types of gender expressions than has ever happened in the United States. The flexibility is there to explore and become who we are and it is my greatest hope that this trend continues into perpetuity. I am a benefactor of this recent trend. I guess it would also be fair to say that I have also helped establish a social climate in which freedom of gender expression is welcomed and encouraged. So has anyone else who has acted in an accepting and loving way towards queer folk (so thank you).*

There was a time when this wasn’t always the case. Twenty five years ago Matthew Shepard, a young gay college student, was lured into a deadly trap in Laramie, Wyoming. He was tortured and beaten, then left for dead tied to a fence. When he was found his face was solid red, covered in his own blood save for where his tears ran down his cheeks. He would later die from his injuries. Now I don’t know what Matthew’s gender was specifically, but his murder was a signal to queer folks everywhere about how safe we were.

This is the world I emerged into as an adult fresh out of high school. There were people in my home town who actively cheered on the murder of this young person. I remember having to actually push back against their sentiment. To these bigots, he was just “another faggot who got what he deserved.”

During this time, I had firmly accepted that I liked dressing in women’s clothes. It will come as no great mystery then why I chose to keep this part of me to myself. My partner at that time was seemingly hostile to me dressing this way as well. I had once shared this aspect of me with her to have it thrown back at me in a dismissive way a month or so later. It would be another 15 years before I told anyone else what I did behind closed doors.

In the meantime, I began compiling a secret collection of women’s clothes. I went so far as to have a post office box so that any items I ordered would not come to my home address and raise the suspicion of my partner. At the time, I didn’t put a label on the activity of dressing femme. I didn’t think much about what it meant for my gender. I was married and in a monogamous hetero relationship so my sexuality and gender just kind of seemed like moot points. I was pretty sure I was at least bisexual, but I wasn’t at liberty to explore anyhow.

However, moot points don’t stop the tide from rolling onto the beach. So I went on with my clandestine activity of dressing up anytime I had the house to myself. I would almost frantically change through my clothing collection trying on one outfit after another while flitting around the house. It was fun, sexy, and reassuring. That was enough for the moment.

And yet still, it wasn’t truly enough. I wanted to share this with my partner, which I felt I couldn’t, and more to the point I really wanted to dress this way in public. I chalked this up as a partial result of wanting to be able to share this with someone, anyone, and also because I was denying myself a form of expression. I was also young and full of hormones. I wanted to be out and about, looking as sexy as the women my age who were strutting their stuff around college campuses and malls (yeah, I’m that old). Why couldn’t guys dress femme without recrimination? It was a societal aspect that I would often lament.

There was another interesting phenomena that happened around this time. Trans people were beginning to become vocal and as a result visible. They were staking out their identities and this was rankling a lot of bigot’s noses. 

In a shitty rural town a few miles outside of my shitty rural town there was a person who had come out as trans and had transitioned to living as a woman. As you can imagine, virtually no one was willing to accept this person for who they were. I remember a male coworker who was a cousin to this woman would refuse to use her name or feminine pronouns when discussing her. By deadnaming her he was making a point, chiefly, that he was an asshole. It didn’t matter that she was family, all that mattered to him was to display intolerance and homophobia with vehemence. Anyone who has ever spoken to someone like this coworker of mine will readily recognize that for these people insecurity is the hallmark of their masculinity. It is a weakness parading as a strength.

I had never met or seen this young woman, something which remains true to this day, but I had an attraction to her nonetheless. Admittedly at the time, the very idea of her as a transwoman was fetishized a bit in my mind. However, there was something much greater at work. I felt a kinship with her. Somehow we were the same but I couldn’t put my finger on it exactly. I had some hunches though. 

First, I figured that she was more liberal than most of the folks with whom I was surrounded. Keep in mind that the world had yet to be introduced to Caitlyn Jenner so I didn’t know that people could be queer and still support a political ideology that would legislate them out of existence.

The other part of my attraction was that I knew there was a tie between her being trans and me dressing femme. It took me a while to sort through it, but I realized that there was a shared experience between us. She was able to ditch certain gender norms (admittedly in favor of others) and live how she wanted and I was trying to do the same. She had conquered the gender expectations against which I was still struggling.

Meanwhile time prodded along, as it always does, and I left the relationship I had previously mentioned. Soon after, I moved across the country and into a much more progressive area. It was here I immediately realized that I had an opportunity to live openly as a queer person. I embraced it head on and soon after I had my sexuality tacked down as pansexual. I also started mentioning to people that I crossdressed.

The term crossdresser for me was a peculiar fit. This term had previously seemed like a fetish label for folks and not an identity term. As such, I was reluctant to adopt it. As I went on dressing in women’s clothes I realized that this activity went deeper than just a fetish. The term crossdresser felt good, as it was the most accurate one I had to describe myself, but it still fell a little short of full representation. I knew I was missing something but I didn’t know what.

I started doing the mental work concerning whether dressing femme meant that I was really trans. At that time in my life, all I knew about being trans was that those folks wanted to live as the opposite gender into which they were born. 

It is true that there is a part of me that would love being a woman. I revel in the idea of slipping into women’s clothes and filling them out in a way that is more conducive to their design. I would love to have small A or B cup breasts. The idea of having sex as a woman is appealing as well. Not to mention that when I wore a skirt or dress outside as a woman, no one would give it a second thought. I would be turning heads for all the right reasons. As an aside, I fully realize that being a woman comes with its own set of hassles, mainly in the form of men who have toxic behaviors.

The idea of transitioning to a woman is tantalizing, but it would also mean giving up a body I have come to love. I still wanted to enjoy my body and to occasionally revel in my flat chested appearance. I love how my penis creates a bulge beneath women’s clothes and I could never give up that sexy bump. I knew pretty quickly that transitioning wasn’t something that I was interested in mainly because the effects were permanent. If I could pop body parts on and off like a glorious gender bending potato-head doll then that would be amazing. This would be the life experience which would bring me the greatest level of happiness. Short of that impossibility, staying male bodied and adorning myself in femme attire is next in line for my quotient of greatest happiness.

I kept the label of crossdresser for 8 years. I continued dressing in private and I was able to find some partners I could dress for here and there. Still, my urge to dress femme in public had never left. In fact, I felt it all the more. I was denying something intrinsic to who I am. 

This led me to start exploring gender terms and concepts. Originally, before I began reading about identity terms I thought bigender might describe me best. What ended up resonating with me most though was the term genderfluid. Simply, this was because my gender identity and expression do not seem fixed. At times I feel less or more masculine, less or more feminine, sometimes like a man, and oftentimes like a woman.

Later on I read an article and realized that being genderfluid places me in the transgender camp. I had two feelings simultaneously. The first was, “am I trans enough to adopt the label?” I quickly realized this was nonsense. The bigger feeling washed over me in a wave of warmth and acceptance. I felt as if I was home. Every emotion and experience of my life came rushing in to fill the space behind the door I had just opened. It all made so much sense now. My feeling of connection to every trans person I had ever met or read about hinged on more similarity than I had realized. We direct kin in our big beautiful queer family.

This self realization, coupled with my desire to dress femme, pushed me to take it out into the streets. I started mixing women’s clothes with men’s and strutting around town. I just bought my first pair of women’s boots to wear in public and little by little I am actualizing what I had merely dreamt about for two decades.

I feel like in many ways that I have finally arrived. That I am where I am meant to be and have finally figured out the nuances of what makes my sexuality and gender work. However, life is good at surprising us and while I don;t know where it will take me, if I stay true to my path I know it will be to a place of happiness.

The other day I was driving to meet a friend and I had a pair of women’s jeans and a women’s cardigan on and I remember seeing my body as I drove down the street and I looked feminine. I felt my heart swell.

Some may find labels limiting and I completely understand what they mean. For me though, I have used them to derive an identity that was previously out of reach. I am pansexual, I am genderfluid, I am transgendered, and I feel awesome.

* I don’t want to assert that the world is a completely better place. The recent mass shootings, protests against drag queens, and the abysmally low rate at which those who are cisgendered even consider dating a transgendered person are all evidence that we have many prejudices and hatreds that need to be relinquished into the dustbin of history.

Article soundtrack: Ten Foot Pole- can we stop trying to win, White Lung- hysteric, No Trigger- the honshu underground, Mobina Galore- whiskey water, The Used- people are vomit, Bunkface- toxicated, Mixtapes- c.c.s., Adventures- i can’t say