Long Distance Reservations

Hey Guys,

So, I’ve known this girl for about seven years now and we live in different countries—not too far mind you, only about 10 hours from each other. We’ve never actually met in person, but have talked to each other a few times over Skype—neither of us are all too comfortable in front of a camera.
Now, we text and IM each other a lot, about 3-5 times daily, with each exchange lasting anywhere from 1-3 hours. We talk about everything. During this time we’ve become really close and there’s almost no topic that is taboo between us.

In the last few months I’ve started having more romantic feelings towards her, but I’m just not sure if it’s reciprocated. When we text and chat, and whatnot, it can sometimes get very flirty, to the point where I’m not sure if she’s being serious anymore. Now, there are several issues I’m having about this, and whether or not to proceed:

1) there’s a bit of an age difference, with me being 9 years older than her.
2) again, I’m not sure if she feels the same way, as she’s an incredibley hard read.
3) I just found out that she’s been dating a guy where she lives for about a month, but she’s not sure if she’s into him.

Now, I’m very conflicted as to whether or not I should tell her how I feel?
I’m not really afraid of rejection because I believe our friendship is strong enough to survive that, but I don’t want to put her in an awkward spot with her current boyfriend because I don’t really believe that’s fair of me. Any advice in this would be greatly appreciated.

Thank you,


Dear Sean,

We understand your concerns and reservations but all of it is about her and what may or may not make her feel uncomfortable. It’s considerate of you to think of her, but what really should be driving your decision is simply: What do you want? If this relationship could look exactly the way you’d like, what would that be? How would it look? Boyfriend/Girlfriend? Living in the same city? What?

We say this because, for your situation—long distance for seven years—someone, at some point, has to take a risk, otherwise you could go another seven years with no face-to-face contact. Is that what you want? So the first thing we think you need to do is think about what you really want from this. If you’re having difficulty with that task, then write out pros/cons. For example.

Pros of Telling her how you feel:

-She might feel the same way!
-You’ll know where you stand. (Then you can be open to pursuing other women if she doesn’t feel the same way.)
-You won’t have to keep it bottled up inside.

Cons of telling her how you feel:

-She might feel awkward.
-You could possibly lose her friendship
-She might not reciprocate.

Then do the same exercise for NOT telling her.

Whatever you decide to do, you need to understand the consequences of taking that action and be ready to accept them. And since you asked for our opinion we’ll give it, although you’ve got to make your own decision.

Our Advice: If you truly want something more with this woman, then don’t you think you owe it to yourself to go for it? She’s a big girl. She can handle a little awkwardness. And frankly, do you really want this woman as a lifelong friend or do you actually want to be in a romantic relationship with her?  Because if you want the latter, eventually you’re going to grow frustrated and resentful by just being friends with her. And think about the future a bit. Let’s say you choose the friends route and don’t tell her. Well, what happens when she meets another guy. Do you really think you’re going to remain best buds while she gets serious with another guy, or gets married? That’s doubtful. Finally, we don’t think your age difference is a factor. It’s not for you, right? Then it probably isn’t for her. And with time, it will become less and less important if you end up together.

Sean, you’ve got to make your own decision here. Think about what you truly want. If it’s just a great friend, then keep things as they are. If you have other ideas of a romantic relationship, then go for it. There are no guarantees in life. Yes, this could completely backfire and you could lose her. But you know the saying, “Nothing ventured, nothing gained.” That said, you need to be completely comfortable with your decision. If you’re not, then hold off until you are.

We hope it works out for, however you decide to proceed.

Any other questions? Follow-up comments?

Take care,


ps. We hope you’ll share our site with your friends. Thanks.


15 Comments on Long Distance Reservations

  1. yellowbumblebee // November 24, 2016 at 3:16 pm //

    Hi Guys!

    I have a long distance question. I met this guy at a friend’s party. He had just started a sabbatical from work and had 2 weeks at home before going on a round the world trip to figure out what he wanted from life. We really liked each other and went a date. We saw each other every single day after I finished for for a week and a half, until he left. That was 3 weeks ago. In the first 2 weeks when he first left, he called me a lot and texted a lot. Less so now, but I get at least 1 message the least every other day. However, he still doesn’t know if he wants to come back to this country or his job and definitely won’t be back until Jan. We have said how much we like each other and what an awkward situation this is.

    Rationally, I feel like I should just let him go and let our affection fade as he may decide never to come back and all this would have been for nothing (and worsening the potential pain). We are still getting to know each other but he isn’t in the right place to be giving me a lot of time. We have talked about this on multiple occasions but each time we agree to continue talking. Do you think we should just let it go?

    Thanks for any advice in advance!

  2. @Yellowbumblebee……If you are able to stay open to other possibilities while getting to know him, then why not keep it going. But sounds to us that that could be difficult for you and the last thing you want to do is spend a year or longer hoping something is going to work out and miss out on other opportunities. (We’re not just talking guys. We’re talking fun. Other adventures. Whatever.) And you need to be honest with yourself. Truly honest. As per him. If he wants to keep talking let him make that decision for himself. You don’t even have to bring it up unless he wants to talk about it.

  3. Hi Guys,

    I’m kind of in a position like the original poster, except I’ve been talking to a guy from another country (I’m in the U.S., he’s from Australia) for about 8 weeks. I like him a lot but I’m not sure if he likes me the same way. He used to text me everyday but then tapered off. If I text him first, he’ll answer me. It’s hard to gauge his feelings because even when he texted me everyday, he never talked to me long or asked me any questions to keep a convo going.

    I realize part of this is my fault because I won’t speak up. I feel it’s not my place to force him to share his feelings if he doesn’t want to. Both of us still have our dating profiles up and use them, so it’s not like I can’t date other guys. But it’s driving me crazy because I like him more than the other guys I’m talking to. Advice?

  4. @Wanda…..Sounds like he’s having second thoughts. Or maybe doesn’t see the point of a long-distance relationship. Does he ever initiate contact? Has he talked about visiting you?

  5. Thanks for taking the time to read my comment. I found the courage inside myself and told him I was cutting it off. It sucked and I still feel crappy because I’m still attracted to him, but I feel it was the right thing to do. He said he understood and that he still wanted to stay in touch with me which I don’t quite understand why. We never met or talked on the phone. Only did texts. I’m not going to say anything for a month to see what happens.

  6. @Wanda…..keep us posted. And good luck.

  7. hey guys
    A couple years ago, I met this guy who lived in a different state then I was. They were visiting my state because their aunt lives in my state and is a close friend to my aunt. We talked and hung out a lot and I really liked him, but I didn’t know if he felt the same for me. This recent year i found his social media accounts & I followed him and he followed me back. We have been keeping in touch for a while now and I really like him. I’m not positive if he likes me back though because we live in different states. Do you think we could ever be in a relationship although the miles?

  8. @Eleanor……It’s definitely possible, but it would be best if he initiates any sort of conversation about it. But let’s say he’s shy, or is afraid of embarrassing himself, or being rejected, you could always hint that it would be fun to get together. BUT…do nothing more than hint. The guy needs to be the one to initiate in this type of long distance situation. Why? Because if a women initiates and the guy is into it, she won’t know if he’s truly into it because of her or because he thinks he’s going to have sex.

  9. Hi,

    So about two months ago I went to Tampa and on my last night, I met someone. Initially, I didn’t want anything to happen between us. We talked for a couple of hours and then we hooked up. I didn’t think anything of it afterwards because I know I’m not going to see him again. When I left the next day he ended up texting me. I found out he’s in the coast guard and he’s actually stationed in Hawaii. On his last day in Tampa, we talked on the phone and he told me he’d hit me up whenever he can. We didn’t talk for about a week. I tried calling him but it didn’t go through so I sent him a Snapchat. He responded immediately and he told me that he uses a different number in Hawaii. We ended up talking on FaceTime that night and he told me that he wants to keep in touch. We’ve been talking everyday since then except when he has to be away for work which only happened once so far for about two weeks. We’ve stayed in touch for the past two months, we text everyday, we FaceTime on the weekends. He plans on coming to see me in Nashville whenever he comes back out here for work sometime this year. My question is, should I pursue this relationship further? Or should I treat him as a friend that I might possibly have sex with if ever he’s in town? Our conversations tend to get sexual at times but we do talk about deep stuff as well. I don’t know, I’m lost in a sense that I don’t know how to treat this relationship. I feel like it would be difficult for me to not fall for him if we talk all the time but then again it’s hard to cut off our communication because I do enjoy talking to him. So lost right now, please help.

  10. @Jane…..We understand. Honestly, at this point we think you should treat this as a guy who you like talking to and who you might have sex with when he comes in town. Unless he initiates some sort of conversation about a committed relationship, then you have to assume he’s not thinking that way. Make sense? Thoughts?

  11. Vanessa Yip // February 14, 2017 at 9:24 pm //


    I really need your opinion guys. I met a guy last summer when I was traveling in Vegas. We were only able to spend one night together but had such an amazing time together. We are world’s apart from each other but promised each other to keep in touch. Then during around fall, I went to visit him in his hometown when he was back in the States. He offered me his place to stay at right away. For the whole trip he has been nothing but wonderful and attentive. I even got to meet his parents haha…and apparently they took a liking to me. After he left, we continued to stay in touch. But the thing that irks me a little is I would initiate the conversations 80% of the time, which we would talk maybe once or twice a month. Though every conversation we’ve has been pretty incredible and he is extremely engaged and do seem interested to get to know me. But now he’s back in the States again, he hasn’t messaged me. I know he has absolutely no obligation to and I shouldn’t expect anything. But the last time we talked, we’ve expressed how we really want to see each other again. I don’t know if he is actually that interested in me or just sees me as someone to bang when he’s back. Or could he possibly be waiting for me to contact him? Many thanks in advance!

  12. @Vanessa….Don’t fall into the familiar trap. You’re starting to second guess yourself and wonder if maybe you’re doing something wrong. (He’s got complete control of you and he knows it.) The fact is, he’s putting in zero effort. Unless that changes drastically, nothing is going to change with your relationship. Meaning, right now, you’re a fun booty call. Sorry. Our advice: Let him start initiating. And stop making it easy for him.

  13. Hi!

    Thanks so much for the reply. I really appreciate it. And you’re right, but obviously my stubbornly hopeful self is giving me the benefit of the doubt. In which I am just giving him excuses after excuses (he’s terrible at texting, it’s because of the long distance, he’s busy with his life etc). On top of that he’s real nice and sweet every time we talk and keeps saying to keep in touch, which makes me even more unsure and confused.

  14. @Vanessa……Remember, sometimes a non-action reveals as much as an action. Make sense? No one here is doubting that he’s sweet and nice. He’s just not showing signs that he’s as serious as you.

  15. Yes, it totally makes sanse. Thanks again!

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