Should She Travel The World Or Settle?

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Question: Hi ATWYS,

I posted this about 2 weeks ago, and I’m not sure if you got it, so I’m sending it again.

I have been actively looking for a partner for two and a half years, and haven’t had a second date with anyone I felt good about. I approach dating on the basis that it takes time to build rapport and attraction, so always accept second and third dates (within reason) but none have blossomed into a relationship so far.

My lifestyle is pretty adventurous – my business allows me to spend large chunks of the year in some great overseas locations, and I often spend 3-4 months in one location before moving on to another. This has led to some amazing experiences, and I’ve met some fantastic people, but there haven’t been any romantic adventures so far.

Last year, I decided to stay in the US to find a relationship, and after 12 months of online dating, speed dating, going to relationship coaches, attending seminars, buying products related to attracting men, and approaching / fliritng with men in real life, I haven’t met anyone with “relationship potential” I have now made peace with the fact that I won’t get what I’m looking for.

By relationship potential, I mean someone I can see myself spending a lot of time with. Enjoying holidays with the family together, travelling together, having fun and supporting ourselves through life. I believe in investing time to get to know the guy better, but if there’s no platonic attraction, I don’t see the point in taking things further.

Ideally, I’d love to meet someone who I can do all the above with, and whose work allows him to travel with me. An entrepreneur, full-time blogger, freelance writer… an adventurous guy who ditched the 9 to 5 to be the master of his own destiny. Deep down though, I know that a man like that in the 40-55 age group can easily attract a younger, more attractive woman. In fact, I’ve met them while travelling, and they have their pick of very young exotic beauties.

I’m ready to resume my travels and focus on work again, but family and friends are pleading for me to stay and keep on trying. When I explain that the options available to me are limited, and that my ideal man has the pick of younger and prettier women, they look upset and say things like “if you had more self-esteem/confidence, you would have attracted him by now”.

Logically I know that I can either lower my standards and force myself to make a relationship work with a man I won’t be happy with, or carry on with my previous nomadic life, be open to meeting new people, use the skills I’ve learned in the US, and let whatever happens to happen (even if that’s nothing).

The second option sounds more realistic. What do you think?

Here’s what I think. We all know that the first part of my answer will be that you are the common denominator. Therefore, since you’re the only consistent factor in each experience or situation, the issue probably lies with you. That’s just plain common sense.

But let’s look at this from a different angle.

I was on Twitter yesterday and came across a tweet that ended up haunting me for the whole day. It said:

I’m the type of girl that falls in love with Justin Bieber because I’m not the type of girl that boys fall in love with.

I identify so closely with the young girl who wrote that tweet. Like her, I’m not the type of girl that boys fall in love with. Meaning I have never been and never will be that girl who always has men swooning over her. My formative years were mostly spent alone, my only company the characters in books or on TV. I knew that young girl who wrote the tweet because I was that girl, and still am to some degree.

That tweet brought me back to those nights when I’d climb into my Dad’s car after a school dance. He’d ask if I met any boys, I’d say no. He’d grow quiet – obviously pained for me but didn’t want me to know – then say, “Don’t worry. Your time will come.” Then we’d get ice cream. I try to imagine what it must be like for a parent in those moments. How powerless they must feel when all they want to do is make their child feel better. Here we are almost 40 years later and memories of those night in the car with my father brings me to tears.

I wanted to reply to her tweet and say what my Dad used to say. Don’t worry. Your time will come. But I’d add one thing: It might not look like what you think it will look like.

A promise like “your time will come” is a loaded one. It implies that, simply by being, we will find someone to share the journey. I happen to believe that if someone truly wants a partner, then they can find one. That was something else my Dad always said. Take this excerpt from a letter he wrote me:

Now, to answer a question you ask me most of the time to which I always say it is up to you if you find someone. My real answer is that I hope so before my time is up. I would ask God of nothing more than to see you happily married.

I guess what I’m suggesting with all this is that it’s up to you if you ever find someone. I have to say that, from your letter, I hear far more passion from you when you talk about traveling and your job than I do when you speak of pursuing a relationship. Maybe the travel and the experiences is “your time.” You’ve found something to love. There’s no rule that says you have to pair off like an animal on Noah’s Ark. That’s an idea that gets planted in women’s heads as we grow up. We mature believing that we’re supposed to want that. We don’t ever seem to consider the possibility that not everybody is destined to have a great romance or “soul mate.” We weren’t all born to be the type of girls that boys fall in love with.

That doesn’t mean we can’t have that, if that’s what we truly want. Like I said, I think we’re capable of having exactly what we want if that desire is a true intention and we’re willing to sacrifice and work for it. I guess it all comes down to how badly you need and want that. I happen to think that many relationships are borne from need. The need to fit in. The need for reassurance. The need for attention. That’s why most of those relationships have short shelf-lives.

An entrepreneur, full-time blogger, freelance writer… an adventurous guy who ditched the 9 to 5 to be the master of his own destiny.

I want to point something out to you. Take notice of how you frame a man who lives his life pursuing his passions as “the master of his own destiny.” Notice the power you assign to him. Where’s that same level of regard for yourself? There’s something very satisfying about being in control of your fate and purpose in life. We’re conditioned to believe that men who lead an unfettered lifestyle are self-possessed. But a woman who doesn’t settle down? Well, there must be something wrong with her. Even your family and friends perpetuate that idea with comments about how if you only did blah blah blah then things would be different. Stop listening to them. They are not you.

I think your second option of maintaining your nomadic lifestyle not only sounds more realistic, it sounds a hell of a lot more fulfilling and fun. You can find men to share your life for a time, should you want that. That’s not hard to do. You’ve tried all these ways to meet someone and nothing has worked. Maybe that’s because you really didn’t want them to work out. Maybe it’s time for you to be honest with yourself about what you really want and why you pursue a relationship with such vigor.

Right now, you are bound by nothing. That’s actually a pretty ideal place to be at this point in your life. So take advantage of it.Think you have a fatal flaw keeping making you unapproachable or that sends a distress signal to men? Figure out what it is and fix it, if only because everybody should commit themselves to personal improvement and growth. Don’t do it because you fear being alone. No thought is more dangerous to women than that. A remember a reader of my column once telling me that if I didn’t stop being so picky that, like the cheese, I will stand alone. Or maybe he used a musical chairs metaphor. Whatever the exact quote was, he was telling me that if I didn’t hurry up and pick somebody I could end up without a chair.


Oh. I don’t suppose he could have been projecting just a tiny bit, could he? Nah. Of course not.

Live your life for you, not the expectations or hopes/fears of others.  There are no wrong choices when you lead an authentic and honest life.

What about you readers?

  • If you could pursue one dream in your life, what would it be?
  • Do you have “well-meaning” relatives and friends telling you that you need to change if you ever hope to meet someone?
  • Is the author of this letter being realistic in what she’s looking for in a man?





  1. Yes, my family told me to change if I wanted to find a successful relationship – mostly how I presented myself – it took years and years but it worked out and I’m enjoying the companionship and “adventure” of exploring a different phase of life. Its absolutely not for everyone but it worked out for me.

    I am a little confused by the OPs statement about not having been on a 2nd date that she “felt good about” in 2.5 years. Yet she keeps going on more dates with men in the hopes of having “attraction and rapport” materialize. Seems like a huge waste of time.


  2. OP, in my experience, and although it may seem not only counterintuitive but culturally heretical, extensive and regular travel make one a less capable partner, not a better one. Long-term relationships/marriage are about the willingness to endure predictability, rootedness, routine, and boredom—with the occasional moments of romance or crisis tossed in. You don’t learn vital LTR skills by partying on the Thames, hiking in Thailand, browsing the Hermitage (St. Petersburg) or dining in the night market in Taipei. The series of short-term relationships (if they can be called even that!) that seem to dominate Western expat life teach nothing except that one should constantly chase variety. Which is of course antithetical to the pursuit of LTR/marriage. It’s not possible to chase 2 horses running in 2 different directions.

    From the tone of your letter, it’s hard for me to imagine you as Suzy Homemaker, cooking and cleaning and showing up to PTA meetings. You may not fully admit it, but you’ve already crossed the Rubicon. I have too. No problem.

    But a road that is different is not necessarily wrong. Your current path might be ideal: you’re building up cash and international professional networks. Grab all the cash on the table immediately. Exchanging money for some dim hope of future romance doesn’t seem wise to me. Econ 101: a dollar today is always better than a dollar tomorrow.

    As I pack my own bags for travel in a few weeks, maybe consider the German proverb, “Trust in motion.”

    And money.

    Or you could give it all up and apply for a managerial position in the suburbs and plow through endless profiles on Match, Tinder, Bumble, do speed dating, etc.


    1. Yeah, I second everything you say Speed, with the addition that OP needs to follow her passions only because she might\ cause collateral damage to innocents if she didn’t. This is speaking from experience of course, as a daughter of a frustrated unfulfilled mother who desired independence and a career but was stuck with mommy duties instead, and later on as a wife of a former “nomad” who wanted to do what was “normal” by settling down with kids, only to decide after 11 years and two kids later that he missed his former “adventurous” lifestyle.
      So OP, please do yourself and others a favour and follow your dreams and passions so you and others may not get hurt.


  3. OP doesn’t mention what her job is or where her money comes from. That’s fine! This isn’t about whether she works or has an inheritance stocked away. It is, however, about whether she understands what she’s really asking for when she claims to want a successful entrepreneur. So she wants to date someone who works 60-70 hours a week and has no choice but to put in a lot of face time with his employees? Or how about that freelancer – the person who generally still needs to do 8-10 hours of work a day even though it’s being done at home/on the go. To me, a major part of the problem is that the men she wants to date are at home in the houses they own, doing their jobs every day. What OP might actually want is someone who has worked his way up the ladder to the extent that he gets 10-ish weeks of vacation time a year. That’s really as good as it gets unless you get honest with yourself and admit that you actually just want to date a rich guy who doesn’t need to work.

    OP needs to accept that when you make a choice, you might be closing other doors forever. There’s a cause-and-effect that happens when you decide to pull yourself out of the dating realm at a young age. You can’t turn back the clock later on.


  4. Pretty much same boat as you, but I am not really successful at work, but I don’t care too much, I like normanding around. I do have a boyfriend now. Sometimes i feel stuck, we get to travel a lot, but I prefer to actually change the place I live, every few years. There are guys out there that also likes to move around.. Just do you eventually you will meet someone, if you don’t then it’s not ment to be. When you love someone, you will have to compromise because there is 2 of you now. Just have to make sure that person is worth it.


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