How do I keep him interested while he’s away?

Dear Guys,

Where do I begin?

I met this guy when he was dating a friend (not a close friend) about 5 years ago. We hit it off right away, but only as friends. About a year into their relationship she cheated on him for the first time. (My friend has a horrible cheating record and we all knew it would happen at some point.) This guy and I talked, connected, and shared a kiss. We both knew it was wrong and I told him to give her another chance, and he did. I was beginning to have feelings for him, but never pursued him because of the circumstances.

Fast forward a couple of years. The two broke up for good this time and he moved back to his hometown, which is five hours away. We kept in touch as friends over the years. Talking for a few hours every 5-6 months. I got in a relationship (which I’m trying to end amicably but I haven’t been happy for months..) and time moved on.

Now up to date: He was having a going away party because he was leaving for the army.  At the party, most people were wasted so we got to hang out and talk the whole night. He was being very flirty with me, brought up old times, and kept putting his arm around me. I got a little drunk and told him how I’ve always had slight feelings for him. He told me that he has too and he kissed me again. We stayed up all night talking and kissing. I was a little skeptical that maybe he just wanted to get some before leaving for basic. However, he was a gentleman and didn’t try to sleep with me.

Ever since the party, we’ve been texting. Not daily, but enough. He has said, “It really blows that we’re just now getting back in touch. Timing was never our thing.” And “We’ll write eachother and see what happens.” He leaves for basic tomorrow and we talked on the phone for about an hour tonight.

I guess what I’m asking is, how do I keep him interested in me from a distance? Am I reading too much into this? We’re not dating by any means, but I don’t want to lose that opportunity. I can’t stop thinking about him, but I don’t want to come on too strong. I’ve been in a relationship for the past three years and I don’t really know how to do this anymore, especially when it’s someone who is far away with no phone/internet, and someone I don’t COMPLETELY know. Am I in over my head? Thanks for reading my dumb girl ramblings.


Dear Jenn,

Thanks for your question. By no means do we think these are the ramblings of a “dumb girl.” We get it.

First of all, the fact that he once dated your friend has no bearing on this. That was in the past and if she has a problem with it she needs to get over it. It doesn’t sound like you’re worried about that too much but we just thought we’d throw it out there.

We’ve always felt there was something special about a written letter. It certainly is much more intimate than an email or a text. Remember, that’s how our parents and grandparents kept in touch, the golden age of correspondence. And it will give you an opportunity to add a personal touch every time you reach out to him. (Also an opportunity to possibly send small gifts, tokens, little things to remind him of home AND you.)

The other thing you have going for you is that he’s going to be very busy with basic training and he’s not going to be out at the bars every night hitting on other girls. He just won’t have the time, or the energy.

For now the best thing to do is try to keep the connection and energy alive, but let him be the one to get things going. Let him be the one to initiate. Believe us, if he’s really interested—which we think he is–he will want to keep this going. So really you don’t need to do anything but be yourself and trust your gut. Things will become clearer as this unfolds and you start corresponding.

Good luck. Feel free to ask us a follow up question and please keep us posted as this progresses. And have fun!


ps. Please let your friends know about us. Thanks!

Other questions about military relationships: 

Military long distance relationship

Military relationship; what do I do? 

Military gal in a long distance relationship; is it time to move on? 

13 Comments on How do I keep him interested while he’s away?

  1. Anastasia // May 3, 2012 at 11:12 am //

    Hi Guys,

    I hope it is ok asking a question through this section! I saw a couple other ladies do so, so I’m giving it a try 🙂 I just got out of a 5 year relationship about a year ago we’re both 30 so I’m really not sure about dating again even though I’m very outgoing, am relatively confident and very friendly – I like to think I can put people at ease with me (not sounding vain – I’ve been told this). I met this really nice guy online about a week or so ago (I messaged him) and we were both very enthusiastic to meet each other – he wrote me back right away and said I was very pretty and after a few messages we did start texting almost every day. So we did get to meet up last night and everything went well, just a couple drinks and then he walked me home. Our conversation was not one-sided where one person dominated it. I didn’t get any awkward vibes or anything from him and it seems we have a fair bit in common and we’re the same age (30). We sat across the table from each other and I noticed at one point he did brush my hand though of course that could have been an accident. He walked me home but didn’t kiss me – just hugged and we did give each other a hug when we first met. Is it a bad sign that he didn’t try to kiss me after? This was his first time going on a date with someone he’s met online so he might be shy, he did come across as relatively quiet but not overly so. I’m usually used to guys at least trying to kiss me at the end of the first date, regardless of how the date may or may not have gone so I’m not sure what to make of the non-attempt. I’ll never instigate a kiss though – I have no problems initiating conversation and suggesting a date but I’m bad at initiating that final follow-through. He’s finishing his residency for medical school and he’s writing a big exam this weekend so he’s been studying all week so I know he’s probably pretty drained, even though we hung out until after midnight and he still walked me home. I wished him luck on his exam (it’s 3 days, 6 hrs a day!) and he said he’d let me know how it goes. So, I’m not really sure of what to make of just a hug – but then again, the building I live in is connected to a concourse/mall area so it was really well lit and were just outside the entrance to the apartment… so not really conducive for any sort of privacy. I want to text him tomorrow to say good luck on his exam but I’m not sure if I should just wait and let him initiate contact or wait for him to let it know how it goes??


  2. @Anastasia……Yes, you can absolutely ask us a question via the comments section of any post. (Hopefully related to your question.) Be sure to check out the “Relationship Memoirs” page to read some dating memoirs from a woman’s perspective. It sounds like your date went splendidly. What’s wrong with a great conversation and a hug? From our experience a kiss on the first date, especially a blind date/online date like yours is optional. And frankly, from the guy’s perspective, going in for the kiss after a great night is sometimes a risk. Why spoil a good night? If it went well that means they’ll be a second date, which means there are plenty of kisses in the future. So to us, he seems like a gentleman, especially because he walked you home AND didn’t try anything. As far as initiating contact, please let him do so. Once he does, then by all means wish him well on his exam. And after that you can certainly contact him to say hi. But let him be the one to ask you out again and initiate all contact and dates for a little while. Then you’ll really know where you stand with him. We hope this helps. Please feel free to ask us a follow up question anytime. Good luck. And have fun! Please keep us posted as this progresses. ps. And please let your friends know about us. Thanks!

  3. Thank you for the speedy reply! Im not going to tell anyone about it until I know if there is actually something to tell, so I’m going to worry about telling the friend a long time from now.
    He’s just so out my league. He’s has his masters in education and now is going to officer school for the army and is only 28. I’m a 23 year old who works at a chain restaurant, so that’s another reason I needed advice.
    I’ll definitely make the letters interesting. I’m good at that kind of stuff.
    Thanks again for the advice! I’ll come back for any more concerns 🙂

  4. @Jenn……Good luck. And don’t sell yourself short. It’s not what you do, it’s who you are. Take care and keep us posted. ps. Please let your friends know about us. Thanks. You might be interested in some of the Relationship Memoirs. Check out that page on our site.

  5. Anastasia // May 4, 2012 at 9:46 am //

    Thank you, Guys! You replied way faster than I expected. His exams started today and I already buckled and sent him a simple text wishing him luck (I didn’t hear from him yesterday anyway) so I wish I read your response first! But oh well, I’ll definitely leave the ball in his court now if he wants anything else.

  6. Hi Guys,

    Sorry this will be quite a long one, it spans a few years. I have never done this before (writing about personal issues online)…but I can’t really speak to anyone I know right now about this.
    This is about my friend, my best friend (let us call him Alex), who has cared for me as more than a friend nearly the entire time we have known each other. We met around three years ago, but I was in a relationship at that point. Once that boyfriend and I broke up though, he asked me to hang out outside of school more often. I was not in a good place after the break up, but did hang out with him more in large groups. Unfortunately, I quickly fell for a guy he introduced me to that reminded me of my ex. It was a short rebound relationship, but I know it hurt Alex that I went for his friend when he was obviously interested.
    After that it was the end of my senior year, and I was single, so I asked Alex to go to prom with me as a friend. Between prom and the summer before going off to college, Alex and I became very close. I began to think I had feelings for him, and asked him out. Quickly I realized I was unsure of how I felt though, and being in a relationship with him felt odd. I told him this, and since it didn’t feel right to me I broke up with him. I’m not sure if I only thought I liked him as more than a friend, or if I was so used to being friends with him that I freaked out when it became something more.
    At the end of the summer I then became reckless. I was saying goodbye to a lot of friends, and a few guy friends of mine moved to kiss me at this time. These people included Alex and the rebound. I was stupid, leaving for school, and single, so I took a couple of these opportunities knowing nothing would come of it. Alex learned I kissed the rebound though, and became angry. We had a heated conversation, and he decided to not speak with me after that point, which I understood and agreed to. The silence lasted for a month before he broke it with a text, and we became friends again. By this time I was off across the country at school, but we still kept in touch online.
    The last year has been filled with him still caring for me, and me not returning those feelings and dating other people. Now, I am not so sure. I’m starting to feel as if I care for him as more than a friend, but it is hard to tell. We are so close and I know I love him as a friend, but do I care for him as more? Every other relationship I have had started as more than friendship, or it quickly escalated into a relationship. This is very different and I don’t know how to make sense of my feelings for him. I don’t know how to confirm my feelings, and I am not sure if I should tell him how I feel right now. His hopes have been dashed so many times, I don’t want to say this to him and get his hopes up only to do the same thing as before. Also, in roughly three months he will be leaving on a two year mission (we will keep in touch through letters). I am thinking I should keep this hidden, and see where things are when he is back…but it is a long time, and currently he is trying to get over me and date other people. Perhaps when he is back, I will have feelings for him, and he will be over me. I really need some advice on this, how to know if I do have feelings for him, and whether or not I should tell him how I’m feeling now, or if I should wait until he is back.

  7. @Sarah….Here’s our take on this. Obviously you care deeply about Alex, and since you do, you desperately want to care about him like a boyfriend. But it really sounds like you don’t see him that way or feel for him that way. And although we do believe feelings can develop from a deep friendship, most of the time there is an initial attraction that then leads to a deeper relationship. Alex seems like a good friend. Why not keep it that way. That way you’re sure not to lose him. Also, keep in mind that you’ve had plenty of opportunities to be with Alex and each time you’ve chosen other guys instead of him. There’s a reason for that. It may not make sense to you, and you wish it wasn’t so, but the facts are the facts. What do you think? Does this make sense? What’s your plan? It might be smart to wait until he returns. And maybe by then you’ll have sorted out these mixed emotions of yours. ps. Please let your friends know about us. Thanks! And feel free to ask as many follow up questions as you’d like.

  8. Thank you for getting back to me so fast. I know I want to care for him as more than a friend, and it makes sense that I could be confusing that for actual feelings. The fact that there wasn’t initial attraction made me feel shallow, because besides that our personalities work so well together. That could very well be just as friends though. Waiting and seeing how I feel in a couple years would be best, I think I know that but have been tempted to say something to him lately. It is helpful to hear other people say that waiting is a good option, it will make me more determined to think it out and wait. I’m still not entirely sure how I feel, but I have time to figure it out and will try not to stress about it. I’m slightly ashamed I can’t figure this out on my own right now, but i’ll try to get past that and talk it through with my friends.

  9. @Sarah…..Thanks for sharing your thoughts and feelings here. It makes sense that you’re having trouble figuring this out because at this point your heart and your brain are clashing. Like we said, your brain is saying, “Yes. What’s the problem? C’mon!” Your heart is saying, “Hold on. Not so fast. Are you sure?” Time might help this, although time away may not give you an accurate reading. As the cliche goes: Distance makes the heart grow fonder. Hang in there. Our advice: Leave your heart open to other possibilities/guys while he’s away. You may end up meeting an amazing guy and then realize this other guy is just a friend who you’re fond of. And if you’re still single when he returns, well, then you can entertain the possibility of dating him then.

  10. Hi!

    I have a question too about a guy… we are going away on college break soon so I’m really anxious. I’m a freshman in college, this guy is a senior and we share one class. We hit it off one Saturday night and he kissed me, but we actually talked for hours in his dorm, so I feel like it wasn’t purely sexual. The next time we hung out, he puts his arms on my waist/around me when we sitting down at a table watching TV and he leans in toward me whenever I say anything. He smiles a lot and sometimes I catch him smiling/looking at me. He tells me about his family/life/career goals and he teases me too. I feel like there are many other signs that he likes me and wants to ask me out, but I have a few reservations as well. For one, he said he would ask me out after finals and first semester break ends, but he only said this after my friend coaxed this out of him. He didn’t have a very comfortable expression on his face either. I always thought that if a guy was really interested, he wouldn’t wait (although we only have 2 days left at school). Am I just being too paranoid/impatient? Is it a good sign he wants to take it slow? Or would he have made his intentions clear by now?


  11. @Addison….We don’t have enough info. When did you meet him? How long has it been? Our initial reaction is: Two days doesn’t seem like a bit deal. And school/finals seems kind of important. Maybe he doesn’t want to get confused, and/or excited until he’s done with the semester. Seems reasonable to us. But fill us in some more and we’ll offer some more opinions.

  12. @One of the Guys. We don’t have enough info. When did you meet him? How long has it been? Our initial reaction is: Two days doesn’t seem like a bit deal. And school/finals seems kind of important. Maybe he doesn’t want to get confused, and/or excited until he’s done with the semester. Seems reasonable to us. But fill us in some more and we’ll offer some more opinions.

    I met him at the beginning of first semester in August. We had one class together and sat close the entire time. He was always smiley, asked me every weekend how my week was, on Friday he asks what my plans are, and he takes the long way to walk with me sometimes. He also teases me and whispers funny remarks toward me during lecture. I never noticed these small things because I wasn’t interested before, but I started noticing it after I myself became interested. He made a move after he invited me over about 4 days ago to his building and after I told him that I wasn’t looking for a hook up, jokingly saying “you’re gonna have to ask me out first.” He backed off but respectfully continues to touch me when he can (putting his hand on my shoulder/waist, leaning in close.) He texts me too and I think he is interested. I think I may too paranoid/worried that after 3 weeks on break, he’ll lose interest.

  13. @Addison……Thanks for filling us in. You may be paranoid, but there’s nothing you can do. If he loses interest in three weeks, then there really wasn’t much potential in the first place. So just be yourself. And trust that you’re attractive enough and interesting enough that he’ll be thinking about you the whole time on break. And try to be patient. (We know that’s hard) He needs to be the one to initiate and ask you out. If he doesn’t, then maybe all he was interested in was a hook-up. But let’s not jump the gun. Just see what happens and definitely keep us posted. Ask as many follow-up questions as you’d like. ps. We hope you’ll share our site with all of your friends. Follow us on Twitter: @TGPBuz. And share on Facebook. Please help a fellow reader and take a moment to VOTE on our Ask our Audience page. Thanks.

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