Relationship and Dating Advice: Wooing at a distance

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Dear Guys,

So long distance relationships are hard. I know that. What I’m asking about is something even harder— that is, trying to pique an interest from someone who you live far away from. I’m prepared to do what it takes, and I’m committed to going through with this, but I could do with some advice on how to approach the situation.

OK, some background: This girl was a childhood friend of mine, but about a decade ago she moved interstate. Strange as it may sound, from missing her then, I developed feelings for her.

Three years ago, I got to see her again, when we visited her family—we were family friends before they moved—and this confirmed how I felt. We got along well, and ended up staying in touch, though not all that frequently, as she’s a busy person. Anyway, telling her how I felt seemed premature—I figured it would make her uncomortable and only make things worse— so I tried to concentrate on becoming closer as friends and improving communication first. I had written a letter about this to send to her when I found out she now had a boyfriend.

That was just over a year ago, and I didn’t end up sending that letter. Anyway, it may not have been a good idea, but I told her I had feelings for her, and that I realized nothing could come of them given those circumstances but after being afraid of how she might react I realized I just wanted her to know. She actually reacted quite graciously, saying she appreciated my honesty and that she was more than happy to pursue a relationship as friends. Anyway, that went quite well, considering.

Almost two months ago she broke up with her boyfriend; on good terms(relatively speaking) from what I can tell. I waited a month, then told her that I was sorry she had to go through that and let her know that I was still interested, though I just wanted to be friends for the time being. She replied two weeks later, shortly after I asked whether she was busy or if something was wrong, as I’d tried to talk to her when I saw her online. She’d just been really busy, and said she wasn’t interested in entering a relationship for a long time. I apologized for any misconceptions and assured her that I was more than happy to just be friends for however long she needed, but that didn’t mean I was giving up on her.

This was almost a month ago, and she hasn’t replied since, which is starting to seem a bit long, even considering her busy life. Anyway, I’ve decided to wait a while longer, and in another month’s time I’ll message her if she still hasn’t replied. I expect you Guys will have had the time to answer this by then, and any advice on what I should and/or shouldn’t say is welcome. I’d also like to have an idea of how to continue from there: if at all possible. Any suggestions of a way I can get closer to her without crossing boundaries would be greatly appreciated.

Thanks in advance,



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Dear Zac,

Thanks for your question.

Consistent communication from both parties is the key to a successful long distance relationship. But issues often arise because every person is different when it comes to how this actually “looks.” One person might need to talk every day to feel secure and connected, while the other person only wants to talk once a week. This usually causes one person to be upset and the other annoyed. From there, cracks start to appear in the foundation of the relationship, then insecurities grow, doubt looms and then a break up. Unless of course both people are very committed to making it work.

But, let’s not get ahead of ourselves.

From your note one question keeps jumping out at us. Are you sure this woman is interested in you romantically? Based on her sporadic communication, excuses about being busy, and her declaration that she is open to being friends with you, this doesn’t seem like a woman who wants a romantic relationship. What do you think?

To us this seems like your biggest challenge. Because it is possible to woo someone long distance as long as they are interested in some way. If this woman only sees you as a friend, it won’t matter what you do; your advances will fall flat and only make things more and more uncomfortable between the two of you.

Zac, we do believe in going for what you want. And we encourage you to try. But we’re not getting a solid vibe from her. (At least from what you say.) But if you really would like to explore this you need to be direct with her. Sending her gifts, or trying to be funny on some social networking site, or showing her how creative you are by writing a song or making a movie or whatever, is only going to creep her out, especially if she’s unsure about you.

Of course you don’t want to scare her away and tell her you love her either. We think the only way you’re going to be able to woo her is if you actually get together with her first, to remind her how cool of a guy you are. Because right now she’s not viewing you as a potential boyfriend, but more of a family friend.

So is there a way you could just be passing through her town? Or take a trip with a buddy—not your parents—and visit? Or is there a concert or some other event that could give you an excuse to not only visit where she lives, but invite her to as well?

We think this situation needs a jumpstart, and the best way to do that is face-to-face. If that goes well, then you’ll be able to figure out the long distance piece because she’ll then be open to it.

Leave us a comment and/or follow up question in the comments section. We’ll respond here as well. And let us know how this plays out. We hope it works out for you.

Good luck,


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