Relationship and Dating Advice: Wooing at a distance

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,


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,


Read more relationship advice and dating advice from THE GUYS:

Text messaging, tears and betrayal

Dating in my 20s as a single mother

My boyfriend is on dating sites; is he cheating?

Why does he have a secret Facebook page?

From a guy’s perspective; is my marriage over?

He won’t bring me out with his friends

Friends with benefits: why me? 


24 Comments on Relationship and Dating Advice: Wooing at a distance

  1. @Emily…..This seems like a reasonable assessment. Forge ahead and keep us posted.

  2. Janet B. // June 2, 2013 at 5:58 pm //

    Hi guys! I’ve recently started back seeing a guy I met over a year ago. It has always been a semi-long distance thing.(we’re 50 miminutes apart. We stopped talking because he randomly remarried his 2nd wife and it was later discovered and told that it was only way to have his baby girl closer to him. Well, I had moved on from the situation n started seeing someone else. 7 months had passed. He randomly crossed my mind and I wrote him on facebook to speak and it was totally a hi and bye thing on my end. Now, he’s in the process of gettin divorced AGAIN because nothing had changed. We’re back friends and talking and intimate again. Only once. But, he has told me he loves me twice, which he has never ever said to me, let alone shown me. I’m convinced, for my own reasons, that the divorce is happening. The thing now is, he’s grown a little distant. He’s made it clear how he feels about us but I’m not sure how to feel about it. I was in love with him when we stopped talking and those feelings have since resurfaced. I guess my question is, am I wrong for taking him back? And how should we go about this situation? I’m so emotionally invested in him and I’m afraid to lose him again but don’t want to look like a fool. Help!

  3. @Janet….We don’t see a right and wrong here. But let him extract himself first. Don’t muddy the waters right now. Let him get divorced and settle in to his new life before you start something up. That will give you more time to think about what you really want. Good luck.

  4. Hey guys, it’s Emily again, the one with the summer fling from last year. I need some advice on my current situation. Things with the man are great. We are seeing more of each other this summer and as always, he is very willing to go out of his way to make me happy. I have hung out with his friend group a couple of times and his best friend says he is envious of our great relationship, and can’t wait to see us get married. Also, he and a good friend of mine continuously say my guy and myself are girlfriend and boyfriend, despite not having applied the label. My guy brought this up to me on one occasion. However, rather than be a mature adult and discuss it, I pretended to be too tired and not respond to what he had to say. I think he then back tracked and said because of our distance, dating really is the best option. This has been going on for over a year, and I am getting tired of it. He still doesn’t know what love is and I’ve grown insecure of our situation and not applying the label “boyfriend/girlfriend” to it. What actions should I take?

  5. Lambert11 // August 5, 2013 at 11:08 am //

    Dear Guys, My name is Lydia and I’ve been talking to a guy for about 2 months. I’m 18 and about to head to college and he’s 22 finishing up his last semester of college. I’m going to a school in Chicago and he’s staying in Kansas. He’s a great guy who’s everything I’ve wanted. He’s funny and smart and engaging and outgoing. Granted he is older than me, so I love that he’s mature and has some sort of plan for his life. One flaw (or whatever you want to call it) he drinks and I don’t ever and when he’s at parties I can’t help but think he’s with other girls. As summer starts to end, we’ve talked about keeping this going long-distance but we are honest about the difficulty of that. Girls have said, “Don’t stay close, you’ll get to college and change your mind and forget him,” but I’m not that type of girl. I’m not one to date just to date and have never had a boyfriend. I want your perspective: Is this worth it to try and pursue while I head off to college?

  6. Lambert11 // August 5, 2013 at 11:08 am //

    Dear Guys, I’ve been talking to a guy for about 2 months. I’m 18 and about to head to college and he’s 22 finishing up his last semester of college. I’m going to a school in Chicago and he’s staying in Kansas. He’s a great guy who’s everything I’ve wanted. He’s funny and smart and engaging and outgoing. Granted he is older than me, so I love that he’s mature and has some sort of plan for his life. One flaw (or whatever you want to call it) he drinks and I don’t ever and when he’s at parties I can’t help but think he’s with other girls. As summer starts to end, we’ve talked about keeping this going long-distance but we are honest about the difficulty of that. Girls have said, “Don’t stay close, you’ll get to college and change your mind and forget him,” but I’m not that type of girl. I’m not one to date just to date and have never had a boyfriend. I want your perspective: Is this worth it to try and pursue while I head off to college?

  7. @Lambert11…..You say what you want, but what does he really want? The distance can only work if he’s completely and 100% into this relationship. If he’s even a little uncertain then it won’t work. We tend to agree with your friends, but we understand how you feel. Probably the only way to figure this out is try it for a little bit. But before you do you need to have a heart-to-heart with this guy and find out his true intentions. Our gut tells us he’s not on the same page with you. Good luck.

  8. I’ve been talking to my friend’s boyfriend’s brother for some weeks now. I’m starting to like him and we get along great, we even have pet names for each other, but he’s shy. If I don’t text or call him first, he won’t text/call me, longest I’ve gone without talking to him was a week. My friend’s boyfriend says that he likes me but is just a shy person. Should I accept his shyness and initiate every conversation or stop talking to him?

  9. Feelingsoblue // October 31, 2013 at 1:10 pm //

    Dear Guys,

    I have been dating this guy for about 6 months and everything was really great. Was getting to know him, started opening up to him, really care about him. Then during one 5am text session I fell asleep and didn’t reply for 30 hrs. Apparently, this had upset him even though I didn’t realize it. Throughout our relationship…he generally initiates texting, dates etc and apparently…this incident caused him to “test me” by not texting…and we ended up not speaking until day 6 when I texted him. He was very upset with me and had basically given up on me in his head. He said he had a feeling there was someone else (there isn’t) etc. While incredibly smart and successful…he has voiced insecurities about how he looks compared to me and how I am always so busy so after seeing him and us making up, I have made a real effort to reach out and show him I care; even though I always responded to him before so I thought we were ok. So 2 weeks ago he had another biz trip and once back I had a trip so have not seen him for weeks now but he has been acting very strange and distant since that incident. I am always initiating with him, he is slow to reply….I knew something was off. He finally admitted that 2 wks ago – about time of our 6 day non-speak – he has to move to different country for 3 weeks out of every month but will still be in same current country 1 week of every month. He said we cannot be together, it’s not healthy, we would argue, it’s not fair to waste my time etc. I asked some questions and said I’m thinking about what he said. Incredibly hurt by this and so sad as I’m still in a different country. Last nite I had asked him to call me after his meeting…he has not. So my question is: does he genuinely care but is concerned that this will not work because it would be more difficult and his insecurities have just built up…if this is the case …I want us to try…or is this just an excuse to break up….Further details: Quite sure there is no one else involved here, I am 8 yrs older than him…he is 29, every other way our relationship has been ideal. Please help!

  10. @Feelingsoblue…….Thanks for your donation. We do appreciate it. So we’re slightly confused. Do you live in the same country? How often did you see one another? To your question: He definitely seems insecure. And as you know long distance relationships are not easy in the first place. If you factor in an insecure person, this makes it doubly difficult. When you didn’t respond to him right away he immediately started imagining all sorts of horrible scenarios. 1. She’s no longer interested. 2. She’s sleeping with some other guy. 3. She’s having second thoughts about me. 4. Etc. And maybe he realized that he just couldn’t handle this sort of arrangement. That said, even if a guy was insecure, we don’t think he would throw away a good thing if he were 100% committed to it. It just seems like he decided too quickly to move on. So what else could be going on for him you might wonder? The only thing we can think of is your age difference. Maybe he’s projecting into the future and wondering what that might look like. You’re 37 we’re assuming, so maybe he’s worried that you’re going to want to have kids right away and he’s not ready for that. We can’t say for sure because we don’t know him, but that would make sense. It sounds like you’re just looking for some answers, so we’d suggest trying to get him to sit down with you to talk this out. If he refuses to discuss it, then that in itself, is information for you to ponder. It would once again show a lack of commitment on his part, or at least lack of desire, to work at this. Good luck and answer our questions. Feel free to ask follow-up questions if you need to. Good luck.

  11. HopefullyConfused // January 15, 2014 at 12:18 am //

    Hi Guys! So I’m 17 and I met pretty much the guy of my dreams (also 17) at a camp this summer. The catch, he lives in a different state. We text occasionally, but I am always the one to start the conversation. He did start one, but in response to a text I sent him the previous day. He said he doesn’t text much, but he always replies to mine within a few hours maximum. We have some things in common, but I am afraid to ask more about him in case he thinks I’m prying or creepy, or even what to ask him about. I also don’t know if he even wants to talk to me, or if he is just being nice. I don’t want to bother him, but he is a great guy. I don’t have ANY experience in dating or flirting in any way shape or form, and I don’t know how to go about hinting that I like him. At the camp, we spent basically the whole week together. I feel more comfortable hanging out with guys, and so I ended up being the only girl for most meals at his table. He called me “A rose among thorns”, we have some inside jokes, but I am so confused! Everyone else could see I liked him, and my roommates said it was obvious that he liked me, but he hasn’t initiated anything. He is applying to service academies (Air Force, Army, Navy) and so am I, so that is the brunt of our conversations. He isn’t the typical “player” type. He is really caring, so I don’t know if he is just humoring me by replying, or if he is just nervous about texting me. Guys, what is your advice?

  12. Hey Guys,

    I’ve been in an on again off again for almost two years now. We were off all of last summer. I went to visit him and upon my return, he told me he needed time to himself and we didn’t speak for almost 5 months. We have been working of things since the beginning of December and things were going fine. We got into an argument last Thursday. All my fault and I said terrible things. I called to apologize the next morning and he didn’t answer. I also texted him with no response. What do I do? Why would he just flat out ignore me if I sincerely apologized twice and am beating myself up about it?

  13. Hi guys,

    So I met this girl at my best friend’s wedding, and I felt instantly attracted to her at first glance. After a few days after the wedding, I found out that she is 9 years younger than me (I’m about to finish my residency and she is just starting out). I didn’t notice this at first, since she portrayed herself to be a very young mature and attractive woman. We added each other on facebook and ended up video chatting almost everyday or fb messaging for over 1.5 months. Recently (this past weekend), I made plans to visit her at her college in Alabama and spent lots of money going there, while also buying her some gifts along the way. I asked her point blank that I was interested in her but I wanted to know if she felt the same way. She said that she was interested and she liked talking to me, but she said that school comes first right now and she doesn’t know where she is going to be next year (she’s applying to med school). Recently she hasn’t been as responsive as she usually is, but she has been extremely busy for the last two weeks, with exams, volunteering events, and assignments, etc. When I met up with her in person, all we did was study together, grab a nice dinner the second night, and all I got was 3 hugs and a kiss on the cheek once. She isn’t a very physically intimate person, because her ex cheated on her in the past. Was wondering what your thoughts were and if I should still pursue her? We had tentatively planned to meet up again in May back in California where we are both from.

  14. @Jeff…..Weddings are a great place to meet people because everyone is somehow connected to either the bride or groom, which means that everyone has been vetted to a certain degree. That said, if she’s been cheated on AND she’s not that comfortable with intimacy, it might take a while for her to completely trust you. We see that as a bigger impediment than the age difference and her being in school. We’re sure you understand why she’s putting her studies first, but the question is: Is that her way of keeping you at arm’s reach or is she just busy? Question for you: You say you made plans to go down to visit her. Did she invite you or did you suggest it?

  15. Well I suggested to see if I could go visit her. She told me she was going to be busy during that time when I visited her because she has a conference, assignments and two exams that she took this past Tuesday and Wednesday. I guess my biggest concern is that we weren’t that intimate when I visited and that we haven’t been video chatting as much as we did initially. I am hoping that she is just really pre-occupied with what is going on in her life right now, but I have no way of knowing for sure. I has consulted my friends about it and they said to try and distance myself at least for the next few days when she is attending a conference in California. I would like you guys to offer more on your interpretation of the situation and give me a slightly better perspective on the situation. She likes it that I’m honest and straightforward with her, but with women it seems their answers are always more convoluted than what they say.

  16. @Jeff……Ok. Thanks for filling us in. We agree with your friends that you should give her some space. At least for a bit. Another question: Who initiated all those Video Chats? And what were the conversations like? Surface stuff or deeper? Like about her life/family/relationships? And how old is she exactly?….. Our first gut reaction is that she’s acting like a woman who might see you more as a friend. Or she’s not sure how she feels so she’s taking it very slowly and keeping you at a distance. The lack of intimacy during your visit and the fact that she kind of hinted she might be busy when you suggested you might come, concerns us. As much as we hate games, you need to play this right. It would be nice if she initiated some sort of contact with you. That would be the most ideal. But if not, you should probably lessen the contact to once or twice a week max. Look toward meeting up with her in May if possible. The question is: If she doesn’t bring up connecting when you’re both in California, then should you bring it up? That’s hard to say at the present. And we wouldn’t push that issue at this time. Hopefully, she’s just young and new at this, and a bit intimidated that you are 9 years her senior and already done with med school. Keep in mind, if she’s in her early to mid-20s and you’re in your early 30s, she sees you as much older than her. It would be different if you were both in your 30s/40s.

  17. She initially started the first video chat and then we started to do it more frequently. We talked initially about surface stuff and then went deeper. She suggested using this website to get to know one another better:

    We talked about family, life, and I tried to stay away from past relationships, but it sometimes came up. She is 20 years old and turning 21 in May and I just turned 30 2 weeks ago. I mean she even admitted that she doesn’t like to be intimate even with her close friends. Her roommate is one of her best friends, and they hug only once a month. The fact I got 3 hugs and a kiss on the cheek the second time I met her hopefully shows some promise. I understand that we are in two different places in our lives right now, but I really think she is the whole package. She is at a conference this weekend, but I’m wondering if I should just not respond to her if she messages me back (at least for this weekend), or if she does, try to keep the convo to a minimum. I don’t want her to lose interest in me.

  18. @Jeff…..Ok, this sounds more promising than we initially thought, especially since she initiated at the beginning. That said, you need to be cool. She may be more mature for her age, she may find you interesting, she may be attracted to you, but she is only 21 and in a totally different stage in life. This probably needs to move at her pace rather than yours. Also keep in mind that her friends are probably commenting on the fact that you’re so much older. Some may think it’s really hot, and others may think it’s creepy. That’s normal, and both camps will become more moderate if the two of you become a “thing.” We don’t see any reason not to respond to her if she texts you, just keep it light, fun, flirty. Keep us posted. ps. You do realize this is going to be a long road. We’re just wondering if you might want to be open to other possibilities, in addition to pursuing her. At least until things become clearer.

  19. Hey guys,
    So I haven’t received a reply back yet from her fb message. I doesn’t appear that she has seen my previous message, but I can’t tell if that’s for sure or not. I know she is busy, and the last thing I wrote to her was hope you have a safe flight to California and have fun at the conference, which was yesterday when she arrived in California. Should I be worried? She usually replies back within a day but its been like 2-3 days since she saw my second to last post, but didn’t reply

  20. @Jeff…..She’s probably just busy with the conference, but like we said, you need to be cool. If this is going to work it’s probably got to be at her pace. Let her be the one to contact you next. You ask: Should you be worried? Well, we do think it’s a 50/50 chance that it will work. The distance. The life-stage difference. Those are obstacles that can be overcome, but only if both people are way into it. This won’t work if she’s luke-warm. That said, why don’t you let it play out a little bit more. Give her some time to respond. And keep us posted.

  21. Hi guys! So she replied back with the following message:
    “Hi Jeff, sorry I disappear off the map when I travel.
    I had a good, but extremely exhausting weekend. I am still recovering, but this is going to be a long week as well -.-
    I got the brace thing you sent me(?) thank you so much i need to go to the doctor to check it out, parts of my finger go numb lol
    I hope you had a great weekend/week!”

    Now initially I was really happy about this, but a lot of friends have been telling me to ignore her until after my board exam next Wednesday which I agree with. But I also want her to make the next move…what should I do guys? Should I just try my best to forget about her? She’s got an important TED talk for her college this weekend, but I want her to make the next move. I have yet to text her back and would like your opinion? Thanks

  22. @Jeff…..We tend to agree with your friends. It’s important for you to focus on what you need to do. (Board Exam) Quick Question before we give you our feedback on whether to contact her or not: What’s her background? Is she from the USA or some other country? Anything else you can tell us about her? Religion? Anything that might give us some insight?

  23. She’s Vietnamese. I’m Chinese. Both of us were born in the US. She’s agnostic and has had her ex cheat on her in the past. Anything more you want to know

  24. @Jeff…..Ok. Good to have this info. Thanks. Factoring in her cultural heritage and her past experience with men, and the fact that you’re older, we can see why she might be keeping you at arm’s length. Why don’t you want until next week to contact her if she doesn’t contact you before then. And then just be yourself. That’s the best advice we can give you. She’s either into you or she’s not. And if she’s not, it won’t matter how you play this. If she is into you, and you don’t smother her, or make her feel that as if she can’t relate to you because you’re older, then it will probably slowly develop into something. But seriously dude, stop fretting about every move. You’re doing fine. You’ve gotten a lot farther than most guys would considering the circumstances. Have fun with it and keep us posted. Hopefully the next time you reach out you’ll tell us that the two of you are an item!! ps. We hope you’ll share our site with friends. Thanks.

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