“Should I Go Abroad To Rekindle A Romance?”

I am in my final semester of college, and last year, I had the chance to study abroad in a country that I’ve been fascinated by since I was 15. I arrived with plans to travel, learn, and do volunteer work. I did NOT go with the idea of romance. Naturally, I ended up meeting someone my first month — a wonderful guy six years older than me named Diego. I would like to clarify that my time abroad did not revolve exclusively around Diego — I made some very dear friends, did well in my classes, and traveled as much as I could afford. But I eventually went home, of course, and Diego and I never discussed attempting anything long-distance. As heartbroken as I was to leave, I comforted myself with the assumption that I would get over my “international fling” as soon as I occupied myself with other things, but the truth is, I still think about Diego every day, and always with sadness.

After months of waiting to “get over it,” I started seeing a therapist, who raised the possibility of going back. Then, my supervisor for my tutoring job discussed teaching English abroad after college, and now I find myself incredibly tempted to do it so I can go back to the country where I studied. My concern is that I want to go for the wrong reasons, and if things didn’t go anywhere with Diego, I would feel like an idiot; I’m terrified of further heartbreak and the humiliation I’d feel for being so naïve as to try to rekindle a youthful passion. On the other hand, I do want to take a couple years to just work and live anyway before tackling grad school. I could really use some impartial counsel from someone whose judgment I admire. Do you think I am being foolish or is there merit in going back to give things a legitimate shot while I’m still able? — Enferma de amor

Yes, it’s true; if you return to Diego’s country to teach English, you do run the risk of heartbreak, but surely a young woman who seems as emotionally intelligent as you do understands that the things in life most worth pursuing usually hold the greatest risk. That’s not to say that everything that’s risky is worth pursuing, but if, when weighing the risk of heartbreak against the risk of always wondering “what if,” the former option is the one you can live with more easily, then in this case, the risk is certainly worth the pursuit. It’s like I said in one of my earliest columns: “If we only pursued relationships that didn’t involve much risk, we’d miss out on some of the richest and most character-enhancing experiences life has to offer.”

Of course, there’s no way I can tell you whether things with Diego will work out, but I can almost guarantee that whether they do or not — whether your time abroad ends in heartbreak or long-lasting love — you will grow and evolve in ways you may not even imagine just yet. Whether you end up with Diego or not in the end, you will leave the experience a more evolved person — one who will go on to love, and be a richer, well-rounded person to be loved in return.

But, let’s be practical here. We are talking about a man it seems you maybe haven’t been in touch with since you last saw him. It’s certainly worth reaching out to him and discussing the option of you returning to his home country. It’s also important to consider whether there’s enough adventure to be had for you there outside any potential relationship with him. You say his country is one you were fascinated by from the age of fifteen on. Does that same fascination still apply, even after spending a semester there? Is there enough interest outside Diego to warrant a return trip back — one that will be much longer this time around? Maybe by making a list of other benefits to be had, you could again avoid making your life there revolve around a man. If you can do that, I feel pretty certain that even if your experience ends it heartbreak it won’t be one you’ll regret. Can you say the same for your other option — the one that leaves you wondering “what if?”

Follow along on Facebook, and Instagram.
If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.


  1. fast eddie says:

    If he’s still available and interested, go for it. Passing up this shot will haunt you for a long time. As Wendy said, you see the risk and intelligently weighting it against the benefit. Worst case is you’ll have an adventure and learning experience. Playing it safe and secure is less satisfying and not nearly as romantic.

  2. Also, see if he is on Face Book. Maybe that will give you some sort of an update on him. Good Luck!

  3. Wolvie_girl says:

    I’ve often said (and even on this blog) that “You broke up for a reason” and therefore don’t usually encourage attempting to rekindle romance…but in this case, the only reason seems to be an ocean! I say go for it. I agree with Wendy that you should reach out to Diego before-hand. It would be awful to show up in a foreign country you just travelled to for a man, only to find that man happily with someone else. I’m suddenly reminded of the Felicity premier when Felicity transfers to NYU for Ben, only to find him with another girl and her face covered in egg…priceless television, but not so priceless to recreate in real-life, an ocean away!!

  4. LW, you seem to have your head on straight so, as long as you’ve thought though what you will do there if this romance doesn’t pan out, go for it! As Eddie said, worse case, you’ll still have an adventure and learn a lot.

  5. ahh Wendy. I love your advice for this LW. It’s exactly what I’d tell my friends if this situation suit them. 🙂

    p.s love the little cupid on your homepage. so cute lol

    1. Thanks! The cupid was Drew’s idea.

      1. Ahh, what a romantic! You go Drew!

  6. And just think, even if things don’t work out, you’ll at least answer that “what if” question.

  7. TheOtherMe says:

    I agree with everyone else, if he is willing to give it a try, go for it !
    I also wanted to add that is is probably the most well written advice seeking letter I have ever read, as LK7889 said, you really seem to have your head on straight !

    Buena suerte !

    1. I have to concur; this was, if not the best, than at least one of the best written letters I’ve ever received.

  8. fast eddie says:

    Aside from the romance element, the opportunity to teach ESL in a different country is fantastic and likely to be of greater value to you and the students then here at home. If you do this I’d love to hear about it.

  9. MellaJade says:

    Wendy, you gave some great advice on this one and I totally agree. Reading both the letter and the response reminded me of a quote I loved from the movie “Girl Next Door”
    I’m paraphrasing, but “You have to find out if the juice is worth the squeeze.”
    Best of luck LW!


  10. JennyTalia says:

    All I know is if you don’t take the opportunity, you’ll spend the rest of your life wondering what may have happened if you did. Go for it – you only live once and to me, an opportunity to be happy forever is worth the risk of some heartbreak.

  11. Chicago_Dan says:

    One vote for team Diego!

  12. Like others said, try to reach out to him first (if you’re not still in touch). If you’re going JUST to rekindle a romance, you might want to test the waters first with some online communication. That being said, if travel is in your heart, and teaching is what you love to do, you can’t go wrong. You’ll never regret an experience that makes you a stronger and more well rounded experience.

  13. What a sensible letter writer.

    If it’s what you want to do anyway, go for it.
    From what you’ve written in the letter, it doesn’t appear you’ve kept in touch with Diego. Have you? I don’t know if I’d even want to see him out if I didn’t have any indication that he felt at least remotely the same way.

  14. Definitely get in touch with him. If he’s moved on and isn’t interested in a relationship, give yourself a couple weeks to see if you still want to go and teach abroad. There’s tons of places to teach abroad, and probably plenty of cities in Diego’s country you could experience 🙂

  15. fast eddie says:

    Someone wiser then myself said that two things stand between us and happiness, fear of the future and regret for the past. That’s a bit slight for all life’s challenges but worthy of consideration.

  16. She never said which country is Diego from… I’m curious. I might help her if Southamerica is the location.

  17. Great advice Wendy, and from everyone else as well – I just wanted to chime in to say that after college I moved to a new city to see if I could re-kindle something with an ex -it didn’t work out in the end, but I’ve never for a minute regretted it. Before moving I set myself the condition that I would only move if I got a job that was in the field I wanted to be in – that way I didn’t feel like I was putting myself at a disadvantageous career-wise, but once I got one, I went for it. Ultimately, I just thought if I didn’t go for it, I would never have been able to stop wondering what if, and truthfully, right after college, there’s often little reason to be anywhere in particular – why not where that guy is? You don’t want to ignore your other priorities, but relationships are an important part of life – one that’s worth just as much effort as your career is – we’d all think it was legitimate to move for a great job. I didn’t end up with that guy, but I still feel really brave and proud of myself for going for what I wanted.

  18. without a doubt, my first thoughts running in my head while reading this letter were just good ones. LW seems to really weigh the pros and cons of going. but, outside of a romantic interest, she seems to have legitimate reasons other than that for wanting to go. the fact that you’re able to even ask yourself, “would i be going for the wrong reasons?” speaks a lot about the maturity and common sense you seem to have.

    i think that is your answer right there. even if it doesn’t work out with this guy, you could still have a wonderful life over there and, who knows, meet someone else.

  19. Marie Parks says:

    @Isabel: Just out of curiosity, why would the country make a difference?

    1. @ Marie Parks: I assumed Diego speaks Spanish and so do I. I’m from Southamerica and live in Santiago. I might help LW if she comes to my country. Now that you pointed out, actually it makes no diference and probably Diego is not even his real name.

Leave a Reply

Your email address will not be published. Required fields are marked *