Dating and Romance

How to Turn a Long-Distance FLING into a THING

long distance

Remember that unbelievably sexy guy from the surf shop that you fell in lust with on your vacation? Or the one with the massive shoulders and shining skin that you had a steamy little fling with while you were visiting your girlfriend in Greece?

Ever wonder if you could turn those intense sparks of erotic connection into… something more?

Ever think that a crazy-hot fling could turn into a passionate dating relationship?

“Last summer, I shared an incredible 3 nights with a guy from the city I was vacationing in. Fantastic sex, plus he took me out, guided me around, and even carried my luggage to the airport. After we parted, there was some mutual cyber-stalking, and when I messaged him on his birthday, he said he “remembers our summer days quite often.”

I will be spending a few days in his city next month, and I contacted him to ask for help arranging transportation. He provided advice, and when I confessed I would be happy to see him, he invited me to stay at his place, which I accepted.

From his answers on his dating profile, it seems he’s open to a relationship and would be willing to try something long-distance in the beginning.

Claire, can a past fling turn into something more? What would be the ingredients to facilitate such a transformation? IF he still seems into me in person, and IF these new days together prove equally great, how can I tell him that I’m interested in getting to know him?” – Julia

Hi, Julia. Thanks for your message (and thanks for your thoughtful comments on my site).

Of course a sexy fling can turn into a dating thing. You have one MAJOR obstacle facing you (see below), but that mountain can be climbed. Lots of people have done it successfully, and you can too.

As to your question about how to tell him you’re interested in getting to know him… Keep reading, gorgeous. I’ve got you covered.

The single biggest obstacle that you’ll face is simply getting to know each other.

Most people who head into long-distance relationships have already been dating a while when suddenly his work transfers him to another area, or her job puts her in a new country for 6 months.

The two of you don’t have that dating foundation.

You don’t know his friends, family, or how he lives day to day. You don’t know his dreams, personal values, history, or habits. You don’t know the state of his finances, or how he communicates, what makes him feel loved, or with what kind of grace he gets through everyday problems… Or, more importantly, how he gets through big, life-changing problems.

You can certainly learn ALL these things and more, and it can be exciting to discover and unlock these kinds of details about a person.

Long-distance relationships can have several advantages over traditional dating…

  • Couples who make a relationship work long-distance are probably going to fare well when they face other obstacles in their couplehood.
  • Because you have fewer interactions face to face, each interaction you DO have can be much more meaningful.
  • Since you don’t get to see each other in person very often, long distance couples tend to avoid the trap of making everything about sex. Your relationship has to become more than physical.
  • Each of you gets plenty of time to pursue your own dreams in life.

WARNING: If you plan to be exclusively committed to one person for a long-distance relationship, you’ll also have to accept a certain amount of loneliness in your life… However, if you’re simply dating casually (and still seeing other guys), it probably won’t cause problems.

How to turn a long-distance fling into a relationship

1. Make the tech work for you!

Text, email, Skype, chat, FaceTime, Google Hangout, social profiles – you have more choices than ever before to connect. Use ’em! And be creative. What about a Skype movie date, where you both watch the same movie, and chat about it while you watch?

2. Put plans in place for QUALITY interactions

If you already have a relationship in place when you go long-distance, you don’t often have to plan for this. But if you’re just getting to know each other, and just doing it long distance, this one is going to take a little effort.

The key is in asking really good questions…

36 questions that make couples fall deeply in love

melt his heartYou may have already seen a recent article in the New York Times that has been going viral on the internet.

It describes a clinical study where a researcher had strangers ask each other 36 questions that resulted in them falling in love.

The author of the article tells the story how she tried out the experiment herself with an acquaintance and was shocked at the power that these questions had on the two of them...

→ Find out more about the 36 questions that made strangers fall in love

3. Send love letters and care packages

Remember how amazing it feels to actually get something in the MAIL? (Remember mail?) (No, the other kind. The good kind.) Whip together a steamy love letter and enclose it with some fun little gifts: a book of erotic poetry or a pair of your line-up-the-back stockings. Or you can go the good old-fashioned route and send home-baked goods. Just do it!

4. Phone sex (oh yeah)

I’ll let you do your own search on this. But the basics are to talk about what you’re wearing (or not wearing), how you make each other feel, and what you’re doing to yourself right now. Or what you wish he/she would do to you right now. You get the idea.

Want help learning “the language of desire”? Read THIS, girlfriend…

Btw, one of the best parts of phone sex is that you can unleash your fantasies. Work through your favorite sexual fantasy role play over the telephone line and see how long he’s able to hold off before calling you again for moremoremore… 🙂

5. Schedule regular visits

You might not be able to be together on a regular basis, but you can and should make definitely plans to visit each other.

While you’re together, hide some little love notes, secret messages, photos, playlists, small gifts and other treats for the other person to find later. Some great hiding places: cereal box, stack of dishes, coat pocket, sun visor, lingerie drawer…

6. Pursue some common hobbies together; encourage and support each other

If you both always wanted to run a 10k, start training together, even in your separate locations. Keep each other updated on your progress, and even arrange your first race to be during one of your visits!

Here are some other ideas:

  • Bike a century
  • Take a class online together
  • Play a game together – board games, MMORPGs, whatever works
  • Learn to speak a foreign language
  • Plan a vacation or trip
  • Build a website together or share a (private?) blog
  • Watch a concert together
  • Research each other’s family trees and share your results

How to let him know you’re interested in a (long-distance) relationship

This is actually much easier than you might think. Choose a good time when the two of you are face-to-face, and not under time deadlines or other stress. Then:

  • Tell him some of the things you’ve enjoyed about your time together recently.
  • Describe some of the things about HIM that you really like. Ways he makes you feel, qualities he has, skills or abilities you sincerely admire.
  • Describe the kind of causal, long-distance dating relationship that you can envision with him. And keep it lighthearted, like this: “I could see us starting to really get to know each other over the next few months. We could Skype and email, and maybe I’ll finally tell you how I got that funny scar on my ankle…”
  • Then ask him: “So. What do you think? Would you like for us to get to know each other a little better?”

Be sure to find out his initial expectations for how often you connect once you go back to long distance, but be willing to be flexible and open. This will be very much like a regular dating process, but will simply take a bit more time, intention, and willingness to adapt.

Ever done the long-distance thing yourself? Add your story below…

I’ve done this a few times, but never with someone I didn’t already know pretty well. If you have experience, advice, and helpful tips, leave a comment below and add your voice to the conversation…

xoxo Claire

22 comments on “How to Turn a Long-Distance FLING into a THING

  1. Claire, this is great, thank you soooooooo much for the article! I really, really appreciate that you took the time to answer my question so in-depth, and to provide so many great ideas! You ROCK!

    Of course, I liked the ideas themselves. And most of all, I loved the sense of excitement and hope and reassurance, that I felt while reading it. To tell you the truth, what I was feeling most anxious about was not HOW to maintain a long-distance relationship, but… what comes before that. How do you get there/agree to try one in the first place? How do I know he’s interested? How do I let him know I’m interested (I will use the little script you gave me!! Thank you!!!)? How do I show him that it’s worth investing time and energy in getting to know him? Or the age-old, general question: how do I make him want me? Of course, I realize that the last one sounds quite bad, haha. I understand that the key is to keep it casual and low-key, and proceed with openness and curiosity, rather than with hard-and-fast expectations. Wish me luck, I’m gonna need it.

    Once more, thank you sooooo much!

    • Claire Casey

      You GOT this, girlfriend. And you’re absolutely right: “Proceed with openness and curiosity, rather than with hard-and-fast expectations.” That way you don’t come across as desperate or clingy, but rather beautifully self-assured; the kind of amazing and compelling woman that every man hopes to win for himself.

      Hope to hear from you again sometime, gorgeous. xoxo CC

      • Hello again Claire! It feels so good to see that this post is still popular, and it keeps helping other women in more-or-less similar situations! 🙂 And I realized it’s been 4 months and a half since I was asking for your help with this, and SO many things have changed in the meantime, and I haven’t come back with an update… so here I am, with a lengthy and self-reflective report! (Spoilers: your tips helped a lot, but with ANOTHER man! Life can be so ironic sometimes…)

        So, here’s how my story went: I did indeed get to see the guy from the post (let’s call him Guy#1) again this summer. I went to his city and stayed at his place, and he was kind to me and the sex was still good… and I realized that in the end, *I* didn’t want to try anything (long-distance or not) with him. I still respect him and find him immensely attractive and fascinating, it’s just that now I can see that he was never actually interested in more than a (repeated) fling. How do I know? Well, by simple comparison with Guy#2.

        I met Guy#2 around a week after this article was posted (end of May 2015—good thing I wasn’t waiting around for Guy#1!). 🙂 Just like with Guy#1, we also spent a few amazing days together (including the fantastic sex, going out, and even the luggage-carrying!). And it’s also a long-distance situation (I currently live abroad and he’s back in my native country—fortunately, I want to go back there when my work contract ends next year anyway). But the similarities stop here:

        – While Guy#1 was content to look at my profile from time to time and merely reply to my messages, Guy#2 has been making a constant effort to contact me (it gradually increased to the point where he’s messaging me every single day now, if only just to say goodnight).
        – With Guy#1, the level of connection didn’t change between the first and the second time we spent time together in person; with Guy#2, intimacy GREW organically (for starters, it helped that we talked, you know…).
        – Guy#1 didn’t make any plans to meet in person again; Guy#2 flew to meet me in September and arranged to spend 4 days together, and is planning to do that again early next year (I’m going to travel to be with him in November).
        – Guy#1 never really cared about my life (or anything much about me beside entertaining me while I was right in front of him; Guy#2 constantly cares about me and supports me in my projects.
        – Guy#1 never spoke about introducing me to his friends and family; Guy#2 plans on making me meet his friends, and even asked me if I want to meet his Mom.
        – Guy#1 never said he doesn’t want to be with me, but he never talked about wanting it either; Guy#2 did, at two different levels: after our time together in May, he insisted on keeping in touch/”dating” long-distance so that we can get to know each other (at my request, it was an explicitly non-exclusive arrangement—because I was going to see Guy#1 soon, ha!); and after our second “batch” of time together (September), he confessed that he’s not looking for anyone else anymore, he’s waiting for me and he’s ready to move in together with me the very same day I come back to our country (which I said I won’t do because I will need at least a few good months to regain my footing in my old city and find a job and reconnect with friends and establish new roots on my own—and he understood that, thank God); he didn’t demand exclusivity, or a commitment, he just offered it on his part.
        – Guy#1 had potential; Guy#2 has interest in me, and is at a stage in his life where he wants to and *can* turn that into something concrete.

        With Guy#2, for the first time in my life, I’m learning what it’s like to be pursued, and I now have the clarity to see that, in the case of Guy#1, I was just deluding myself by seeing MUCH more interest than there really was (hey, I had no idea what *real* interest from a man felt like!). And (again for the first time in my life) I learned what it’s like to have deep, scary, purposeful conversations about a relationship (candidly discussing expectations, sharing what we need, and comparing timelines for things like living together, marriage, and having children) and to consciously decide that “this could actually work, so we’re both willing to give it a try”. Wow, eh? 😀

        So, I’m actually pretty optimistic about my chances with Guy#2 (Claire, please DO let me know if I’m deluding myself again!!!!). Here’s why:
        – The interest and desire to make it work is mutual.
        – He’s located where I already wanted to move back to, and where I had, and will have again, a life of my own.
        – There’s a clear (and relatively short) expiration date on the LD-ness: In October 2016, my work contract ends, and I’m moving back to our city.
        – We’re both aware that “doing healthy relationships” is a learned skill, and we’re both willing to educate ourselves on the topic.
        – We both make it a priority to spend quality time together on Skype: talking, watching TV shows together, reading blogs and listening to podcasts and discussing them, and, yes, having cybersex… So we’re basically combining all but one of Claire’s tips from the post above (I’m also thinking of applying #3 and sending him a not-your-typical care package…). And it’s working wonderfully so far (thanks for the advice, Claire! I didn’t get to use it with the man I initially wanted, but I’m using it with a man who actually deserves it much more).

        As for Guy#1… He didn’t say anything since I left his city in June (didn’t even reply to my goodbye note). But in September I edited my profile on the website he (Guy#1) had initially found me on (to reflect the fact that I might have found someone special so I’m not currently available—note that I still didn’t delete said profile!), and I had the bittersweet surprise of finally hearing from him (Guy#1) again. He reminisced about our beautiful time together, and wished me all the best and happiness. It felt bittersweet. 🙂

        So, what conclusions would I draw from this whole long and extremely rambly report? (Claire, please correct me if I’m wrong!)

        1. It’s great to give a LDR a chance; just please, PLEASE make sure it’s something both partners actually want, and it’s not just in your imagination (“potential” and “attraction” and “compatibility” are not enough!). Make sure there’s genuine interest and practical steps that both partners take in this direction (see my Guy#2).
        2. Just because someone is attractive and smart and wonderful AND shows you a great time doesn’t mean they’re actually interested in a real relationship (see my Guy#1).

        Any other opinions, Claire? I’d be very interested to hear your thoughts and advice! And thank you again for this post!!!!

        • I so love this Julia!! You just helped me in so many ways and probably don’t even realize it. I’m so glad you did an update. I hope everything is still going well between you and guy #2.

  2. Christine

    Brilliant cubed! Good luck Julia, not that I expect you’ll need it 🙂
    These principles also apply when there are constraints of distance (my fling/aspiring thing lives halfway across my smallish state), also he’s an involved, divorced parent of two young kids, has them on weekends. So, we’re figuring it out.
    Thank you Julia, for your question & the incomparable Miss Claire. I feel even more confident going forward I can build on what we have so far created together.
    Love, rainbows & unicorns bearing gifts,

    • Claire Casey

      (Christine, it was that “unicorns bearing gifts” that I especially enjoyed in your comment!)

  3. sandmarie

    I’m seeing a flight attendant, it is hard to even see him often. Is this supposed to beon distance relationship when all we do is sex because his stops in my city are always at almost midnight. How can I making turn this into other than sex. HELP I REALLY LIKE THIS GUY.

    • Claire Casey

      Yeah, it sounds like more of a bootie call than a relationship. Do you know if he is interested in more? Have you already asked him? What did he say?

      Also (and this is a big one) — are you dating other guys?

      • sandmarie

        Yes I’m seeing other guys, I’m not intimate with anyone else, because I really like this guy. He has 9 kids with two wives. I’m beginning to wonder if I’m his lover for this destination since he is a flight attendant.

        • Claire Casey

          Wait, wait, wait. If he’s married, he’s not the one for you. And even if he’s divorced, this is gonna be one super-busy man for the next 20 years. If you continue with him, you should at least go in with your eyes open about that.

          Assuming he is NOT married, you still need to know if he’s interested in more of a relationship with you. That means you have to have a conversation about it.

          But I think you can also listen to your instinct in this. If YOU think you’re just another woman to get it on with at this particular layover, then you may in fact be right… Painful, but it’s better to know than to wonder.

          • sandmarie

            He is not married, he is separated and he called me the other day and told me he is going to sent me passes to go meet him in some of his destinations near by. He is 54 and said he is looking for a long lasting relationship to end his life with this person. He told me since he is with me all he wants is a normal life. So help me how can I make sure he is really committed. I get texts, daily and even videos Etc. He tell me his whereabouts all the time. Yet I feel not quite right about just meeting up for sex and dinn. Os. He is addicted to my food I’m a great cook.

  4. sharon bunting

    We live together. Been seeing him since last November. He’s a very good lover to me an me too him we make each other so hot for each other. He made me get off 10 times the first time we made love. Maybe its just my mind over thinking

  5. sharon bunting

    No he’s the only guy an I’m his only one too

  6. This was everything I needed plus more. Thank you for this!

  7. Hi Claire,
    I have been seeing a Wonderful guy for over a year now.
    We are in a casual Boyfriend /Girlfriend friendship.
    At the end of this year, both my kids and I will be relocating to another state to live.
    I’m happy to move because of a new start with my kids and I.
    I’m going to be sad to say goodbye to many of my friends here and yet it’s going to be tough for me to say goodbye to my special friend to which I really want to have a long distance relationship with. …. distance from one another will be an 8 hour drive .
    In my heart of hearts I’d love for us to be together forever but he also has commitments and can’t be with me :/
    We click, we are the best of friends and he makes me feel good about myself and as I do for him. ….
    What do you think Claire? Can it work for us?
    T.i.a…. much Love JJ

    • Claire Casey

      HI, Josy Jo, thanks for writing. As you your question “Can it work for us?” — I don’t see any reason why not, but I definitely don’t think you should sit around and wonder about it. That last section of this article is perfect for you, because your best plan right now would be to have that chat with him. Then you’ll no longer be wondering, you’ll KNOW! 🙂

      The only concern I have has to do with the nature of his “commitments.” My hope is that you’re not telling me he’s married…

      If he’s NOT married, there are very few commitments that can’t be worked around for two people who love each other, so be hopeful. But most of all, talk with him about it and see what happens.

      You have absolutely nothing to lose by finding out, right?

      My best to you! xoxo Claire

  8. Hi Claire,

    I recently started seeing a guy before he left for the summer. We go to different schools in the same city but he recently went home for the summer while I am still at school for another couple of days. We are from the same hometown, and I will be returning soon. We really have great chemistry and get along pretty well. He also asked me when I was landing and for how long I would be home. I think we could pursue a more serious relationship. When he first got back home a few weeks ago, we were still texting back and forth (pretty regularly every day). However, he started not answering my texts one day and the next week, to make sure he wasn’t ghosting me, I sent a check in message. After a few texts back and forth for about a day and a half, he didn’t answer AGAIN! A few days later, he drunk texted me and, the next day, I answered and we had a short conversation about what he had done that night.

    All of my friends say that this is not a bad sign. They say that he is probably in “summer mode” and realizes that he will be seeing me in a few days, so doesn’t really see the point in starting a conversation. I think that he has lost interest, but there are no signs in our conversations that he is not interested in me anymore. I’d really like to see him when I get home, but I feel weird doing so if he hasn’t reached out over the past few days. Thoughts?



    • Claire Casey

      Hey there AMI. There’s a fair amount of work involved in keeping up a long-distance relationship. And pretty much everyone who has ever been in one has had periods of less communication and then times when both parties worked harder at it. It’s a habit you have to get into, and life sometimes intervenes, you know?

      I don’t see any reason why you shouldn’t keep dating this guy. BUT! I also don’t see any reason why you shouldn’t also continue to date other men as well. You’re in school, which is the perfect opportunity to explore and enjoy the many kinds of possibilities around you.

      Hold yourself a little in reserve, and if you want a real relationship (rather than a fling) don’t immediately jump into bed with anyone. Give a man a chance to win your trust and show you if he’s truly interested and is willing to do the work of a relationship with you.

      Here are a couple of articles that might be helpful to you:

      There are so many good things in store for you! I’m sending you waves of sunny-ocean love. 💚

      • Claire Casey

        I meant to also say — Sure, text him when you get home! It’s easy enough to do. Just don’t “chase” him — if he doesn’t come halfway, let him go. xoxo

  9. Hi Claire,

    Loved this article, thank you so much! HELP, I’m feeling so perplexed! Back in February I met a guy online, who lives 5 hours away, and we immediately hit it off from the start. After a few messages we eventually began talking/skyping for hours every night. There hasn’t been a dull moment since! Great conversation, we have the same sense of humor and enjoy the same hobbies and interests. Within 2 weeks of connecting (Valentines Day actually), he drove down her to take me out on a date. It was seriously one of the best first dates I’ve ever been on and it lasted nearly 8 hours. We kissed that night (amazing kisser btw) and then planned for me to come visit him the following week. Which I did and it was yet another amazing moment for us! After that, things began to get confusing.

    The feelings have been mutual throughout this entire process because we’ve both vocalized to each other that finding each other is like finding a needle in a haystack, we’re both very picky. So here’s the kicker, he was engaged and that ended just a year ago because she cheated on him and got pregnant by this other man. She did this while he was here in Texas (she’s in Georgia where he was living) purchasing a home for them so that they could be closer to his family. He told me from the beginning that he was still very fragile and I told him I understood. Because of this I kept him in the loop more so then I typically would because I knew he needed that. Well long story short, I could sense some major distance and it began taking a toll on me so I decided to walk away. I’m 35 years old and I’m ready to settle down and have babies.

    Fast forward, and for the last 3.5 months, I’ve been dating someone else who is local. He’s an amazing guy and treats me like a queen BUT there’s something missing…that something is the guy above. I can’t stop thinking about him. It’s like our souls were supposed to meet. Well so last weekend I took a road trip with a friend to where he lives and simply added him back onto snapchat and within minutes he wrote me. He’s been dating someone else for 2 months now. He still met us for dinner both nights while we were there. On the second night as we were saying our goodbyes he said that he hasn’t stopped thinking about me and I told him the same. He grabbed me hand and I could feel the chemistry. We held each other for so long and tried to figure out how we could make it work. I told him I was going to leave him alone but he said he doesn’t want that. He will be here for work in a few weeks and he insisted on spending time with me. I’m crazy about him!

    Please keep in mind that we feel this way about each without being intimate, we’ve only kissed and cuddled. I want him in my life and I don’t know what to do? Any advice or suggestions would be greatly appreciated.

    Hopelessly confused,


    • Claire Casey

      Hi Erin — Thanks for taking the time to read and comment. And I don’t see any reason at all that you shouldn’t have him in your life. You know what your end goal is (marriage & kids), so keep dating your local guy and date this other guy (follow the long-distance dating tips above) and any others until you meet the one who is interested in the same goals you have and is emotionally ready to commit.

      There’s absolutely no reason NOT to do this, is there?

      Just be aware that the long-distance guy is dealing with some pretty heavy emotional baggage, and will need time and intention in order to figure out what his contribution to the break-up was (and he did play a part), so that he can heal from it and move forward, stronger.

      Sending you sweet healing, fresh mountain breezes… xoxo

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