In this episode, Jennifer shares her experiences dating three pilots, each with unique traits but similar emotional challenges. She describes the excitement and complications of dating pilots—like the "bad boy" who is inconsistent, canceling last-minute and running hot and cold. One pilot would breadcrumb her with promises of romantic trips, while another boasted about securing assets through questionable means. Jennifer explains that pilots often enjoy companionship without commitment, advising those interested in dating them to stay independent and cautious with their hearts. Her takeaway? Have fun, but guard your emotions.

"Dating a pilot can feel like soaring through thrilling skies—just remember, the landing might not be as smooth."

Mr. Pilot

Today's episode features Jennifer, who has experience dating three different pilots.



Who is the bad boy, Mr. Pilot?



You will be breadcrumbed by a pilot and he won't respond to your last text.



He will cancel a date with you an hour before you were going to meet.



Blame it on jet lag or being on call.



He'll be gone for days at a time, but he will figure out how to keep seeing you.



He will request a layover in your hometown again next week.



You won't like the warm and cold you get from him.



He would regularly cheat on his wife and tell you he's separated.



How he'll lure you in.



He has stories to tell from all over the world.



He's open-minded.



He will always share what he's drinking or eating in photos in exotic places, like Paris or European cities he flies to.



He gives the anticipation to you that one day, he will go to these romantic places together.



Spot him before you're hooked.



You don't want to unfairly judge him by his profession because there are a lot of stereotypes surrounding
pilots, such as sleeping with flight attendants, napping in cockpits, having kids in every city, and high
divorce rate, aka AIDS, Aviation Induced Divorce Syndrome.



He could very well be a high-value man.



You just have to make sure that he is the one.



How you proceed thereafter requires insight and preparation.



Dating a pilot can be hard since they are often away and can't be contacted easily.



To survive dating a pilot, you need to be independent.



If this is a deal breaker for you, then you should not get into the relationship and save everyone a lot of tears.





Host: So, Jennifer, have you ever dated a pilot?



Yes, I've actually dated three pilots, and they were very different personalities.



But there were some overlapping features, and I'm sure we'll cover that today.



So, what would you say are the most challenging aspects of dating these pilots?



Well, I think when you go in to dating a pilot, you kind of need to know your personality type and your
attachment style.



So, you know, if you take the Briggs-Meyers test, it'll tell you if you're more intuitive or if you're an emotional
dater.



And for me, I'm an INTJ, so it's hard for me to get attached to people very quickly, which I think you kind of need that personality if you're going to date a pilot.



And if you're more of an emotional dater, I'm not sure that that's a good, like, I don't think that's a good
match, because, you know, the pilots I date were very, dated were very nice to me.



But they definitely wanted to keep it very, to keep emotions out of it.



It was about, you know, having dates and having fun on the dates, but not anything really towards
commitment, except for the one, which I'll talk about, the exception, but what his red flag was.



Host: So how did they lure you in?



Well, I was taking flying lessons, and they were really interested in that.



Female pilots are kind of rare.



They're called diamonds.



So they liked that I was interested in flying, and that I could discuss it with them.



And the first one I'll talk to, he's Mr.Romantic, you know.



He'll talk about all the places he's going to take you, and all the getaways you're going to get on.



He's very nice, but you have to just remember that he is living a very different reality than you.



He can jump on a plane and be in China tomorrow, and that's not your reality.



But he tries to share with you, like it is, and it's kind of a fantasy, but you cannot get wrapped up in thinking that this man is going to start arranging for you to go on these trips with him.



That's not what's going on.



And so, you know, I just, I enjoyed hanging out with him.



He was very nice to me, and it was just to have fun.



And then, you know, another one, he was very interested in helping me become a pilot, and he had his
own airplane, and he would take me flying and let me practice flying, and he was very motivated.



His mother had the same job I have now, and she always struggled financially, so he really wanted me to
become a pilot and work at FedEx and make $300,000 a year, and he was highly motivated that I was
going to do this.



And it was very nice, but becoming a pilot takes a lot of money.



And he did let me practice on his plane, but I did not have the funds.



It takes tens of thousands of dollars to become a pilot, but we had a good time.



He was always very gracious when we went out, but it was understood that he called me, I didn't call him,
and everything was based on his availability.



And it wasn't going to be a boyfriend-girlfriend scenario.



It was going to be a, hey, I'm free Saturday night.



Do you want to do something?



But when we went out, he paid for everything.



He was very generous.



And then the third guy, he was recently divorced, and he actually seemed like this really great, awesome guy.



I was like, oh, this guy is, you know, he's monogamous.



He seems interested in finding, you know, a long-term relationship.



I thought he was really great, and we were getting along, and we dated several months.



And he wasn't great about calling when he was in another country.



You know, he was one of those, he wanted you available when he was in town.



And everything seemed great with him until he told me that his father was an attorney.



And when he was married to his first wife, I think for 16 years, every legal document they signed was
written by his father, including their mortgage documents.



So his wife had a job, and she had worked all the years they were married.



And when they got divorced, she found out the father had written it up so that the father owned everything.



So everything that she had been paying for all the years she was married, she had no legal rights to.



So he got to keep the house in another state.



He got to keep all of their savings.



He was able to buy a house for cash and call your bill.



And she didn't even get to keep the car that she had been making payments on.



She had no car.



And his sister gave her old car and decided to get a new one.



So she, after 16 years of being in a marriage and being committed, she walked away with the sister's used car.



That's what she got from it.



And the dog.



She got custody of the dog.



So the guy that seemed like, you know, possibly marriage material, he was looking for an extra income to
pay to make himself and his family wealthy.



And you were basically a live-in servant.



And so three very different types of guys, but three guys that you would want to emotionally attach to
because you would get hurt.



So what advice would you give to someone who's starting to date a pilot?



I think if you're dating a pilot, you need to recognize it for what it is.



It's probably just to have fun.



You know, you need to look at this as someone who is like a male friend.



Like you have female friends you go out with.



You need to look at this as somebody that's a male friend.



I can tell you of all three pilots I went out with, just to be completely honest, I did not sleep with any of them.



That did not seem to deter them.



They were okay with that.



I'm pretty sure they were sleeping with enough women that they didn't care.



I mean, honestly.



So if you are the type of woman who, if you sleep with a man, you develop feelings for him, I don't think
you should share that kind of intimacy with a pilot.



If you want someone that would just take you out for a nice dinner or a nice night on the town and have fun
with, and you know, he might even take you on a trip, you know.



Like I said, the guy gave me flying lessons, you know, we went to Little Rock, he had talked about us flying
down to Florida for the weekend, and I told him, you know, I don't want to sleep with you, and he said, well,
that's fine, you know.



But with all that in mind, you need to realize that these men have a lot of options, and it's just a basic
supply and demand.



There's probably a thousand women for every pilot, and they don't have to date someone seriously.



They don't have to settle.



They can have their pick weekly of who they go out with.



And so it's just not a good idea to emotionally invest.



How did you spot them, that they were bad boys?



So the first guy, he was inconsistent, you know?



He would say, hey, we're going to do this, and he'd paint this really over the top picture, and then
something would happen, and he would, you know, and they'd seem to forget about it.



And I think he was juggling some, I don't think it was intentional.



I think he was juggling so many women, and he couldn't remember what he promised.



But he was really, really nice to me, you know.



So as someone just to go hang out with and have fun with, yes, absolutely.



Would I get on a plane and go somewhere with him?



No, because honestly, you might meet somebody while you're there, and forget you're with him, and you
might get left.



And then the second guy, when he told me the story about his dad, and he really was bragging, he was really proud that he had all these assets that he and his wife had, his former wife had paid for.



And he was so proud that he had been able to use his dad's legal, you know, mind to create this, you know, basically a pyramid where everything was under his dad's name and his name.



You know, his dad signed everything over to him once the divorce was final, and the wife got nothing.



And, you know, I didn't, and I'll say this, when a man shows me a red flag, I do not tell them it's a red flag, okay?



And I do that for the next woman they date, because if they know they're showing red flags, they'll hide it from the next woman.



So like this story he told me about taking advantage of the wife, I did not say I had a problem with that story.



I wanted him to tell the next woman he dated that that was something that she needed to have on her radar.



I just said to him like, oh, we've been hanging out for a while.



I don't see a friendship developing.



It's really important for me to be friends with somebody I get in a relationship with.



And I just let it be very neutral.



The third guy, he was fine.



We didn't really, I wouldn't say he's a bad boy.



He was always very nice to me, but he told me from the beginning that he had a vasectomy early in his 20s.



He wanted no children.



He wanted, he did not want to ever get married.



And his main obligation was making sure his mom was taken care of.



So when we dated, he did not want to be your boyfriend.



He wanted to just date.



He was very nice.



But that was not my objective.



I was dating to have a relationship, and he was not.



But, you know, I still think if someone called me and said, is this a nice guy to date?



I would say, yes, he's very nice.



You know, he's just not going to commit to you.



Yeah.



Host: So according to you, maintaining trust, especially with the second pilot, do you think that's a common stereotype about pilots?



I think pilots know that they make a good salary and they share information with each other.



And I would not go into the situation thinking that you're going to be an equal partner.



I think that they are going to watch out for their own interests.



And you know, and I have a unique take on that because I was married to somebody who came from
another country.



And I can tell you that I found out during my divorce, you know, that person had been funneling money to
the other country.



And so, you know, a pilot, you know, he can go set up an offshore bank account easily because, you know,
he's flying to other countries.



You know, he could have an apartment you don't know about that he has girlfriends over at.



And as long as you have a physical address in some countries, you can open a bank account.



And so, I would tell you, from my experience, my ex, when we would go to, he was from Canada, when we
would go to Canada, he would withdraw $9,999 in cash.



Because when you cross into another country, you have to declare if you have $10,000 or more.



So he would triple count to make sure that he did not have a dollar more than $9,999.



And the first thing he would do while we were in Canada is go to the bank the next day and tell me he had to go take care of something.



And then he would go make a deposit.



And I was very young at the time and didn't know.



But the point being that if you're with somebody and they're from another country or they have access to
another country, they also have access to bank accounts in those other countries.



Host: So how did you navigate these emotional highs and lows that come with their inconsistent communication?



I think if you're going to date a pilot, the most important thing is that you're not dating him alone.



I will say with the third pilot, the one that was giving me flying lessons and things, he was investing a lot in
me, and so I did just date him.



You know, I was working, I didn't really want to juggle more than one guy.



So I had a lot of things going on with work, and then I would see him like every other weekend for a night.



But with the other two, I think it's really important.



It's, you know, for dating, I treat dating like a job interview.



You know, if I had a business and I was interviewing for a job, I wouldn't just accept one applicant.



I would have multiple applicants, and I would have multiple interviews.



And when I'm dating someone, I do not become exclusive right away.



You know, they have to show me consistent behavior, they have to show up, and they have to
communicate to me that they want exclusivity, because I have no idea what's going on with them.



I have no idea how many other women they're talking to.



And, you know, I just, I make sure that I don't get emotionally attached until you see that consistency.



And until then, it's just fun.



You're just going out, and you're having fun.



And for me, I think everyone has different attachment styles.



For me, the more physical I become with someone, the more emotional I get.



So I just don't let them become physical with me.



That's just not something I do.



But, you know, someone else, it might be sharing their childhood stories or something like that.



You know, whatever it is that makes you bond with a man, just don't do it until you get that exclusivity.



So independence is often cited as a key factor in surviving a relationship with someone who travels a lot, in this case with a pilot.



Host: So how can one maintain that balance while still feeling emotionally connected?



I don't know that you...



For me, personally, I'm not built that way.



You know, I have a friend who has several children and they're varying ages.



You know, her youngest is about 7 and her oldest is, you know, 22.



And she's so involved in their lives that I think that she could handle a pilot.



I think she would actually like that he wasn't around all the time so that she would have time to focus on
her children.



So, if you have a really active social life and you have other things going on, I think that you can handle
that lifestyle.



But if you, you know, go to work and you're looking for companionship from a man, and you have your
friends, but you do like the consistency of having a boyfriend and going out on dates every week, I just
don't think it's a good combination.



Host: So, given the nature of their job, how can someone discern whether the pilot, their dating is genuinely interested in a relationship, or just enjoying the perks of short-term encounters?



I'm not sure you can know.



I mean, for me, from what I've seen with men, okay, a man, you can tell how much he desires you by how
invested he is in you.



So, if you're dating a pilot, and you want to know that he's invested in you, you know, at the end of the day, I would make it about money.



Because if he can't juggle 50 women, if he's, you know, paying car payments or rent.



And I know that sounds, you know, crazy, but, you know, all three of those guys, if you were really looking at them for boyfriend material, the minute you put that on the table, they would have all bailed, you know.



And so I would just say, look, you know, I understand if you're not ready for marriage, but I'm looking for a provider.



I want to know that you're serious about being with me.



And, you know, this is what I need from a man.



I need a man that's going to make my $500 car payment every month.



Here's my cash app.



If you're serious about a relationship with me, show me that you're invested in me.



And if he's not willing to do that under the circumstances, now, I wouldn't do that with everyone, but that's a way to weed him out, okay?



And if you want to, you know, be, you know, above par with it, you could take that $500 a month and you could put it back in case you get married, and you could say, surprise, I've been using that money to save up for our wedding or the honeymoon, right?



But with them, you have to see that there's some kind of real investment, and a man that's not willing to invest in you is not willing to stay with you.



He's going to just have you on the hook for convenience until somebody comes along that does desire him.



And I will tell you, I think women have really been shamed into, you know, not expecting men to be providers.



But I can tell you that I know several women that demand that men that date them, you know, invest in them, whether it be dinners and getting their nails done or whatever.



And those men value them much, much more.



And, you know, from personal experience, I will tell you, when I was married and my ex-husband was, you know, dating a woman, he highly valued her and gave her lots of money.



And I was working and contributing the money, and he was actually keeping up with how much, I saw notes, he would keep up with how much I was contributing and then go withdraw that amount because he didn't feel like he was losing money because I was bringing, you know, $1200 to the table.



So he would give her $1200 because he wasn't out any money.



So, and he highly valued her.



So a man is meant to be a provider if he's serious about a woman.



If, like I said, if you want to be legitimate, you know, you can put the money back to pay for something like the honeymoon or, you know, whatever you think, you know, something for you guys to do.



But, you know, if a man is, you know, acting interested in you, and then he won't, he doesn't care that you, that your child suddenly needs braces, and you need to come up with $5,000, and you only have $4,000, and he's not willing to put in the $1,000, and he's making $300,000 a year, then he's not interested in you.



You're in his Rolodex.



You're one of many.



And that's just a way to weed them out.



And I hate to be that way, but, you know, it's the same as, you know, a woman.



So a woman's currency is her beauty, and a man's currency is his currency.



Okay?



So as a woman, if you are, you know, buying clothes, you know, getting your hair done, you know, wearing nice shoes, wearing nice jewelry, you're spending money to look good for him.



And he should be spending money on his end to reciprocate what you're doing.



There should be a give and take.



You should not be getting dressed up and wearing your best dress that you spent, you know, $80 on and $200, you know, pair of shoes and a hairstyle that you, you know, had to pay $180 for to go to a man's house to watch a movie on his couch and him expect physical intimacy from you.



He has invested nothing.



That is a lopsided relationship, and that's a parasitic relationship.



So I hope that answers your question.



Host: Yes.



Host: Well, thank you very much, Jennifer.



We really appreciate you coming and giving us your perspective about pilots.