Flyby Romance & Dating Moderates in a Divided World — An Army Pilot Interview

You Can Date Better
19 min readMay 9, 2021

Finding common ground when you’re in the air all the time is a tough gig for moderate military folks. One army pilot gets up close and personal about what it’s like to date when you fall outside common assumptions for a polarized job.

Photo by Bob Smith on Unsplash

A Small Introduction

I come from a military family, however disparate I feel from that at times. My maternal grandfather is a retired Air Force lieutenant general and the last living flying ace from the Korean War. He has a book written about him. He’s a big deal. I love him dearly and respect the hell out of him, even if we don’t share all of the same beliefs and viewpoints. My father was also in the Air Force for a short time long before I was born and I have many family members with past or present history serving in the armed forces. I have very close friends in Los Angeles that are currently serving or former veterans, and have dated a few as well. Getting to know all these people on a deeper level through time has truly shifted my viewpoint on so many aspects of the military stereotype.

Culturally, this military affiliation might seem a million miles away from what I do and who I am, given my ideological tendencies. I identify as liberal, I’m not religious, and I’ve been associated with the arts my whole life. Interestingly, that arts legacy stems from my maternal grandmother (the general’s wife) who fostered a deep love of dance, theatre, literature and appreciation of nature in her children and grandchildren. I spent more than one summer in Alabama with them as a child going to Shakespeare camp, or a ballet conservatory, or attending theatre and art festivals. What an unlikely but beautifully complex combo they were in some ways. I consider those grandparents to be some of my biggest supporters throughout my life. We do not fit the box of assumptions as an extended family, but I think that’s for the better.

There are some big points of controversy in such a mixed bag of a family and consequently, I have to reconcile how to marry these opposing forces from time to time. Indeed, the divide of the country has also been reflected in some portions of my family as well, and I’m not alone in that experience. That’s America right now. This is why this interview strikes a chord with me and why I think it’s important to dive deeper into the nuance of who military folks are, how they change, and where they surprise you. We can assume so much based on so little, and in the dating world, we may write people off too quickly, working off previous bias. I want to try to do that less, and I’m hoping readers will too.

Edward, like my grandfather, is also a pilot, and occupies a non stereotypical space in the military world ideologically. Where does that leave him in looking for a partner? How does he reconcile his own roots, his work culture and his personal beliefs and preferences? His journey from small town Iowa boy to big city dweller and international traveler in an incredibly high stakes job is a great lesson in questioning assumptions. In a world where we tend to look for partners that feed our confirmation bias, I hope examples like Edward might open our hearts to explore differences and expand viewpoints on dating. His interview reminds me that opposition can be a place of growth instead of frustration, unity instead of conflict, and love instead of hate.

Edward! How old are you?

I am 37.

And what got you into the military originally and how did you become a pilot?

I wanted to fly in one capacity or another even as a child, but I didn’t really have an idea of how to accomplish that goal during college. I started in aerospace engineering but I was a bit naive as to what the actual conceptual process of what aerospace engineering was. I thought it was more to do with the “aero” and less with the engineering, so after my first semester of college I switched majors because I didn’t like sitting in a dark closet doing Fortran programming for eight hours a day. I went into political science as a fallback and I didn’t really have a direction at that point. One of the things that I ended up doing with a friend of mine was an ROTC class for the Army. It was just an introductory class and I didn’t really know much about the military. I had some extended family that served in the Army and the Air Force, but it was just something to do. I was nineteen and didn’t really have a direction to go in. I enjoyed it, and as it happened, I was pretty successful in it, and was offered a scholarship after my sophomore year of college. So, I kept doing it and made ROTC my focus, and then that became my direction for after I graduated.

I joined active duty immediately following graduation in 2006 and went through the initial training for my specialty, which at the time was logistics. I got assigned to infantry battalion and after two months, I was deployed to Iraq. So, it was — out of college, training for six months, and then into Iraq. I knew that what I was doing was not what I wanted to continue to do, and I applied to flight school in 2008. Honestly, it was kind of just a pipe dream. I didn’t really think that I would get picked up, but I knew that if I didn’t apply for it I couldn’t get it, and I had made a decision, one way or another — either I was going to get into flight school or going to plan my exit from the military. As it would happen, I got selected to attend flight school three months before leaving Iraq so I started flight school in November of 2008 — a pretty quick turnaround.

Wow. So how long have you been flying now at this point?

My first flight in a helicopter was in September of 2009 so I’ve been flying for about twelve years.

Okay, what do you love about your job right now in the military and what do you hate about it?

The thing that I love is the flying part. I find myself going to places in the country, in the world, that I never planned on visiting or that I didn’t know existed. There’s always new things to see or a new perspective of someplace. And flying an aircraft is such an exhilarating experience. Just having the ability to control a machine like that and make your way through places that humans were never supposed to be, it’s just kind of a surreal feeling and I always enjoy it. Every time I fly it never really gets old.

My least favorite thing is the bureaucracy — of any organization, really — the controls and measures put into place by people who don’t do the job that you do because they think they can control the job that you do, and it’s frustrating. But it’s one of those things that, it’s the price of admission, and if you want to do the cool stuff sometimes you gotta do the bullshit.

How do you look back on your love life and relationships up until now through the lens of the military shaping your young life?

That first five or six years in the army I was gone more than I was home. So, not having a foundation, or a home, or roots really kind of changes the dating dynamic and what you’re exposed to, as far as having those experiences and growing up as a person. I grew in different ways through military experience in deployment with training and all of that, but I didn’t really have a lot of serious relationships in my twenties and that made it difficult to have a shared experience in the dating world.

That’s interesting. I think of the experiences that you had in your twenties as a fast lane to maturing, like they molded you in other ways — with leadership and facing fears and things that most humans their whole life might not ever face, and you are facing them quickly and aggressively. But the relationship side was just put on hold, maybe?

Yeah, of course. Like, I saw people die, I saw people explode, I saw human body parts. Mental maturation as far as trauma and compartmentalizing and grieving and dealing with anger and sorrow, and seeing bad things happen to people you care about — that part I definitely felt like I “matured” quickly. However, how to handle a disagreement or an argument with a significant other — about how to cook dinner or how to ask the right questions when your girlfriend is upset about someone stealing her lunch at work, or whatever other sort of thing that people learn in their 20s — I was excluded from that process by not being in a relationship at the somewhat formative years, so I was twenty-seven or twenty-eight by the time all that kind of shook out. It wasn’t the same experience as people who I’d gone to college with who had married their high school or college girlfriend and by the same time I was coming back from war they had already had a couple of kids.

Do you ever think that it has been an asset to you that you didn’t rush into things? Because you come from a small town in Iowa, is that true?

Correct yeah, from a very small town, a three stoplight town in the middle of Iowa. We didn’t have a lot of the same — I guess “culture” is not the right word — but the population was so small that there weren’t a lot of opportunities for casual interaction. Just a much smaller dating pool of people.

Now, you’ve lived all over the place, you’ve seen big cities and small towns and all sorts of things. Do you have any thoughts about where you came from versus where you are now, and if you have regrets or if you’re thankful for certain things?

Coming from a small town like that, my observed goal of most people was to find a partner, to get married, to shack up, to have a family and create that nuclear white picket fence home unit. That is kind of the Midwest staple of what your goals in life are. Honestly, looking back, I’m grateful for having escaped that. I never really wanted to stay in one place, and the army was an outlet to find that escape. I don’t think I would have had the same experience if I had been married young or in a serious relationship when I was younger, so I’m grateful for that way out. I think seeing a lot of different places and seeing what other people’s results were with that nuclear family unit just kind of strengthened my resolve of what I want out of life, and that in turn has kind of framed who I’m looking for in regards to dating.

I like that. So, what’s your dating life like right now? How are your goals different now? What are you looking for?

It took me a while to kind of figure that out. I was married for two years. As I said before, not having that experience in your twenties kind of leads you to make somewhat rash decisions. It’s not an excuse, just a contributing factor. I didn’t really know what the progress of a relationship was supposed to be so when I found someone that I enjoyed dating I just kind of ran with it and unfortunately, it did not work out — for the better in my mind. I hope that person is happy, I don’t hold any ill will, it was just definitely not for me.

I’m looking for a partner to amplify what I already have — someone to have fun with, someone to spend time with when it works for both of us, to travel with, to talk shit about (laughs), to talk shit with. I’m looking for a friend who I have chemistry with and that’s really it.

I’m interested in how that works for you. Do you date now? Do you use dating apps sometimes?

I have, yeah. In the past several months I’ve kind of shied away from it, mostly because it hasn’t been a very normal dating environment with Covid and with work. I’m still away from home half of the year with training or attending courses. Trying to date when you’re on the road a lot is also inherently difficult and meeting people who are okay with that is difficult too.

When you’re on the apps, what do you show on your profile? What do you tell people about what you do? Do you hide anything at first?

I keep it somewhat generic. On Bumble, the last profile that I had, I said that I was a pilot for the military interested in travel, a transplant to Southern California, and just some random interests — hiking, running, golf, road trips — things like that. There are some filters that you can apply for “I don’t want kids” and I do select that. Honestly, it’s interesting how many people swipe without reading so it’s funny to get matches and then have the first interaction or question be like, “Oh, is this what you do?” or, “Is this really what you want?” and once I tell them yes, that’s honestly what I’m looking for, sometimes that ends the conversation… and that’s okay too. I feel like honesty is the best policy.

As far as the types of people that you date — the military is usually associated with a more conservative crowd and some people might be nervous about that aspect of it. Do you experience that? Do you think people make assumptions about you based on your job?

I think that’s an accurate statement. The general assumption is that most military members are very conservative, probably almost exclusively republican, and I think there’s a lot of anecdotal evidence to back that up. However, I don’t consider myself a Republican. I consider myself kind of just a Moderate and Centrist, and more libertarian than anything else. There are some assumptions. I’ve had people say that they won’t date someone in the military just because they’re in the military without any other disqualifiers, which again, people have the right to do that, but it’s interesting where people draw their information from. Like if they were to ask four different questions, they probably would get answers that they did not expect from me.

That’s kind of where this is going. I feel many folks are less tolerant of people that are moderate because politics has spilled into lots of other areas and we feel that who we’re with represents our own values so we must align on everything. Who are the type of people that you tend to want to date, whether or not that makes sense and whether or not they are interested back?

It’s interesting, I find myself not really looking to match an ideology when dating somebody. There are obviously certain things that are more difficult to get around. Dating someone who is religious would be more of a challenge for me than dating someone who is overly liberal or conservative. Unfortunately, it seems that conservatism has kind of aligned itself with the religious identity, and when people assume that I’m conservative they also assume that I’m religious, and neither of those things are true. It’s weird to get pigeonholed in something by my identity for work and because of that I would say I am more likely to date someone who is left or liberal leaning than conservative. I haven’t had a difficult experience with that as far as being able to connect and not have politics be a problem — with a few exceptions — but for the most part it’s not hard for me to look past that, even if I don’t tend to agree with them on all of their political ideals. It doesn’t make me value them any less as a human or a partner.

You mentioned a few exceptions. Has a belief or political opinion or anything like that been a stopping point for you with someone who doesn’t share the same one?

Yes. The last somewhat serious relationship I had ended kind of abruptly. The person that I was dating had a very passionate view that all police without exception are bad and power-hungry and should not be supported, so essentially the conversation turned into an ultimatum. If I didn’t agree 100% with them then they didn’t want to date me. So I told them that’s not how I deal with conflict resolution and I’m not going to change my outlook on life when I have friends who are police officers and I’ve known police officers that have been shot in the line of duty — I just fundamentally disagree with that position. And if that’s something that couldn’t be discussed or there was no gray area or room for compromise, then I guess that was going to be the end of that.

What are some red flags or hard deal breakers for you in dating?

I guess one red flag would be someone who’s overly dependent because I’m not a person who can be always available, in the sense that I don’t want someone else’s happiness to depend on me and if I’m not available. Just by nature of what I do there are literally days where I’ll be flying for ten hours of the day where I am inaccessible to human technology. I’m flying at altitudes where phones don’t work, and then I get back and I have to sleep at some point because the next day is more of the same, and if that’s something that a person can’t handle then that’s kind of a non-starter for me. Another thing that’s kind of difficult is people that are extreme home bodies. People who are introverts are fine, but people who are afraid to travel, or people who are not willing to expand their horizons…

Like antisocial, agoraphobic…

Yeah. I see a lot of friends in a lot of places and I like to share experiences, so having someone that has difficulty with meeting new people can make it difficult. I’m pretty adaptive based on whatever my environment is, and looking for someone who also shares that quality.

Yeah, it sounds like something you’re also talking about a bit is trust too, because there is another stereotype — and I’m curious to know if you think it’s a worthy stereotype — that especially people with sexy titles in the military that travel around a lot may be prone to stray. Does that come up?

I’ve known enough people that are in and out of the military, that — people who are cheaters are going to be cheaters. I don’t think the Army breeds people who are cheaters or who are disloyal, but there are definitely people who fit that criteria. I feel like it’s just a measure of exposure, not that those people are any more or less prone to cheating, they just have much higher numbers of opportunities.

Opportunity, yes, but what do you think of the loneliness factor, that you don’t have what you need right there with you so you’re more likely to stray?

That’s a fair question. It’s hard to say if the job is the catalyst for that or if it’s just human nature.

What about pilot stereotypes?

Pilots are arrogant but it’s something that we have to do. Being able to do a job that is life-threatening daily, you have to have a certain level of hubris in order to know that you’re in control of an aircraft that is somewhat out of control. So that’s a personality trait that is definitely present, but I think it’s a necessary thing. It’s part of the training. Like, you have to have the respect for something that could potentially kill you, but you also have to have the confidence and arrogance to take control of that thing. There’s a certain sort of swagger for people that have dangerous jobs, but it’s got to be a balance of cockiness vs. confidence. If you have one more than the other, then it definitely shows.

How about assumptions on the civilian side? Like, does a man in uniform really get the ladies?

I try not to really meet someone when I’m wearing my uniform, so I guess I can’t answer that. I don’t hide that I’m in the military, but I would rather get to know somebody without them making a judgment, or making all the assumptions that we talked about earlier — about political affiliation or stereotypes — because it does cloud people’s judgment.

What are deal breakers that others may have about you do you think?

I would say not wanting kids is a deal-breaker for a lot of people in my age bracket. Being independent and wanting to move. I’m not particularly close with family and it’s not that I don’t care about them or have interactions with them, I just don’t really share the values of my family for the most part so I don’t feel the need to live near them or have a lot of time devoted to that.

Do you think your happiest times have been when you’re single or when you’re with someone?

Oof. I would say some of the things that I’ve done with a partner were probably among the top five experiences — going on trips, having moments or experiences with that person — but I can say without a doubt, like, my day-to-day life is better when I’m single.

Ha! That’s funny. I like that a lot because I think there is an assumption that being coupled means that you are finished and that’s where happiness peaks. Do you ever look at your desire for the lifestyle you want to live and then look at your desire for a partner and think, these are two very conflicting things?

I do, and as an example, seven years ago I was dating someone, and we hadn’t been dating very long, but they were of a similar opinion as far as the moving thing, or not being tied to a location. So, as it happened, I was moving for work, and I already knew that I was moving for work before I started talking to this person, and they eventually moved to the same place that I did, and it was great. We had fun for several months, and then it kind of got turned back around on me that it was my responsibility or my doing that that person moved to follow me, even though it explicitly was not. I was fully transparent about the whole situation, and when things started to go badly then I got blamed. Maybe that person was just frustrated with how things were going for them personally, but somehow I was responsible for them moving.

What do you think you’ve learned through your relationships so far and how do you see your growth as a partner?

I’ve learned to be more expressive about what I need. Earlier in my 20s and 30s, I was more concerned about trying to mold myself into what I thought would make someone else happy by saying the right things, and not being expressive about what concerns or thoughts I wanted to address. So, I feel like at this point in my life I’m more vocal about what I’m looking for, what I need, or what I want. I’ve solidified the things that I’m looking for with personal goals for what I want to accomplish with life. I think I’ve learned how to be a better listener. At least, I feel like now I understand that women don’t always want you to solve their problems. They want you to listen to them, even if that means not being able to do anything about it, sometimes the listening is more important. Just based on my background and my outlook on life, I’ve always been someone who tries to fix things or find solutions, and that doesn’t always work, so I try to be better about that.

Okay, let’s talk advice. What are some things you would tell a civilian who is about to go on a date with someone in the military and might need some pointers for common mistakes or keeping an open mind?

Well, I guess there are two categories. If someone in my age bracket has deployed or has moved around a lot already, ask questions. Ask questions about what they want for themselves. But understand that sometimes the answers are difficult for people in the military depending on what they’ve seen or experienced. They may not know if you really want to hear the answer because sometimes it’s a lot darker than what you would expect. Have an honest conversation about how much you want to know about what they’ve gone through. It can be difficult to hear and it can also be difficult to talk about. The PTSD part of it is real, and if they don’t believe that you actually want to know — that you’re just making idle chit-chat — then they’re probably not going to tell you the real story, and if they do find that you’re credibly asking and tell you, that can open up some hurt for them.

As far as looking to date someone in the military, just treat ’em like any other person. People are not cookie cutters. Two people standing in line in the same military organization could have vastly different viewpoints about the world, or not want the same thing, or not believe the same thing. I have a really close group of friends I work with and we rarely agree on a lot of things in the social or geopolitical world. Just because we wear the same uniform doesn’t mean that we’re the same person.

The caveat to that is, for people who are younger or just joining the military and have a boyfriend or girlfriend and maybe are deploying — that person will change. Like, the roles and responsibilities of being in the military will change a person…mostly for the better, but occasionally the stresses and the time commitment required for some military jobs can make it feel like they’re not who you signed up to be with and that can be challenging, especially for young people.

What advice do you have for folks in the military that might be in your boat, that don’t fit the traditional mold and are going out to date in the world to connect with people that might be further outside the ideological dating pool than is expected?

I would encourage anybody to broaden their horizons. Someone you thought that you may not have anything in common with might be the person that opens you up to new experiences or is that yin to your yang. It doesn’t always work when two people are the same person. There is balance to the world and there’s a good balance in relationships.

Have you found that you like a little bit of a challenge sometimes?

There are certain things that are hard things to compromise on, but I would say gaining different perspectives is the only way you learn. If you live in an echo chamber, your viewpoint is never going to shift and grow. It’s not to say you have to change your mind on everything but if you don’t give credence to new ideas then you’ll never be exposed to them. And you never know, you might be the person that can open up someone else’s mind.

Do you think it’s harder in these very recent years to have open conversations with different perspectives than it used to be?

I would say yes, I feel like people have definitely put their jerseys on a lot more. Just on dating apps that I’ve been on and seen, people put hard lines on there. It makes it difficult to bridge those divides and have those conversations like we were just talking about…when people decide that they don’t want any part of the other side.

Are you optimistic about your own dating future?

I always try to be optimistic. I’m still sorting it out. Building consistency is difficult, but I think as the world recovers from Covid and everything that’s been going on, hopefully there will be some reawakening of dating and all that fun stuff. Hopefully!

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You Can Date Better

Writing/content curation by Carrie Prince, founder & boss lady behind — coaching & consulting for the current online dating landscape.