This is the way the story is supposed to go, right?


We meet a great guy, we instantly notice — there’s something special about this one. But even better, possibly, they notice the same about us — there’s something special about this one, I’d love to get to know her better.


After a totally appropriate amount of time — after we’ve gotten to know them a little bit — after a few times of hanging out, when we’re absolutely positive, “Yes. There’s something REALLY special about this one!” he asks us on a date. He likes us, and he’s made his intentions totally clear.


The story doesn’t end there though — he doesn’t just ask us on one date. He asks us on another, and another. And after another totally appropriate amount of time, after we’ve had enough time to get to know him, to realize that we actually have totally fallen in love with this guy, he realizes the exact same thing, and so he tells us. “I love you” and our heart promptly melts as we whisper back what we’ve been thinking for weeks, “I love you too.”


After awhile, he asks us to marry him, we say yes, we have the most beautiful wedding — dancing late into the night under the stars surrounded by our very best friends and our family. People make toasts to us, to how perfect we are for each other, to the fact that they see God so clearly in our relationship, and we ride off into the sunset and live happily ever after.


That’s the dream right? That’s what we’re all hoping for, what we’re all holding out for.


But have you ever noticed (and I totally know you have!) that sometimes it doesn’t go quite this way?


I know I most certainly have.


One of the emails I receive more than any other from my sweet, wonderful, brilliant readers is the email that goes something like this:


“I really like a guy, and I think he may like me too, but I’m not sure because he hasn’t said anything! I want him to pursue me, and I’ve been waiting, and waiting and waiting, and we talk, and we have so much in common, and such a connection, but nothing is coming from it! Do I keep waiting? Do I give up? Do I tell him how I feel?”


Is that your story? It’s absolutely 100000% mine.


The thing is — there have been many times in my life when I’ve had feelings for someone and had no idea if they felt the same.


Sometimes it was with a guy I used to date, but had broken up with. The relationship was over, but I still had feelings, and I wondered if maybe they still did too.


Do I say something?


Other times, this first scenario unfolded for me — well, half of it.


I met a great guy, I instantly noticed — there’s something special about this one, and the more time I spent with him, the more I liked him. But the other half of the equation was missing. Or maybe it wasn’t. I honestly had no idea because I had no idea how he felt, and he certainly wasn’t pursuing me.


Pursuit is something we talk a lot about in our Christian culture. Isn’t it? 


Different moments in scripture lead us to think that if the man is the head of the household, of the family, if he’s the leader, then he should be the pursuer. We should wait for him to make the first move.


And in a lot of ways, this is the story we want anyway! We want a guy to see us, and notice us, and pursue us.


But it doesn’t always happen this way — in fact, more often than not, I think it doesn’t (check out this post). 


But why?


The first reason is actually something I talk a lot about in my course Love Your Single Life — and that is the fact that only one relationship is supposed to work out.


Think about it — best case scenario, if everything goes exactly as it should, only one of our relationships in our whole entire lives will succeed. Every other one will fail. Isn’t this crazy?


If we’re successful in relationships, that means we will have an absolutely horrible batting average. Failure every time except for one.


And this means that we’re likely going to have feelings for a lot of people, a lot of these confusing, convoluted situations, a lot of times when it just doesn’t work out before we finally get to that one where it does.


I know I did.


That scenario that I described at the beginning — that’s how it happened for Carl and I. We met each other, realized there was something really special about the other one, and he asked me out.


But before that happened, there were so many times when I liked someone and nothing happened, or someone liked me, but I didn’t really like them back.


The timing was off, the people were off, the situation was wrong — it didn’t work out.


And so this is the biggest reason why I think we find ourselves in this situation so much more often than not — because only one relationship is going to truly work out, which means that all of the rest of them will happen in fits and starts this way. All the rest will be near misses.


But another reason why I think the story doesn’t play out the way we want it to sometimes is because of something my husband actually pointed out in one of the Bonus videos for the single life course:


Nobody is teaching men how to pursue women.


And it’s really true. It’s the rare man who’s been taught how to pursue a woman. The rest of them are looking around at what everyone else is doing, just trying to figure it out and do their best — just like we are.


And while I wish this wasn’t the case — while I want the wonderful, strong men in the world to help teach the ones behind them — I think that realizing this puts things in context a little bit.


We expect guys to know what they’re doing, and to do it right. Sometimes we even say that we won’t even give them a chance if they don’t do things exactly perfectly.


But I think it helps us have compassion for them, and really see them as people, not perfect pursuers — to realize that they don’t know what they’re doing any better than we do. So they might not know how to perfectly pursue you, or how to tell you if they like you. They’re afraid of rejection, bumbling through it, or totally clueless, just like we are.


So this brings us to the biggest question I think we all have…


If we have feelings for someone, and we’ve waited, and we’ve gotten to know them, and we think there might be something there, but they’re not saying anything, do we speak up? Do we tell them how we feel?


My advice would be, yes!


Here’s why:


When I was growing up, my dad was my go-to guy for boy advice. We would sit in the white wicker chairs on our front porch, or go on evening walks around the neighborhood, and I’d tell him the whole story and ask him what I should do.


And really — I was usually asking for advice about this exact thing.


“I have feelings for them, but I don’t know how they feel, and I have no idea what to do!”


And my dad’s advice was always to put my cards out on the table.


I think the reason we don’t, the reason we want to keep our feelings hidden is because we’re afraid of being hurt. And I get that, because getting hurt is an almost certainty when we’re telling someone how we feel.


BUT… I think we sometimes equate getting hurt with weakness and this is what my dad showed me isn’t true.


When we are putting ourselves out there, sharing our feelings, putting it all out on the line for love — that’s not weakness. That’s not embarrassing, or shameful, or something to avoid. It’s actually the opposite. It’s strong, brave, courageous.


And if we do that, if we tell someone how we feel, it leaves us without regret. We know that no matter how things turn out, we know we did the best we could. We know that they had all the information. We can put to bed all of our what-ifs, and could-this-have-turned-out-differentlys.


So whenever I found myself in this situation, whenever I realized that I liked someone, and we got to know each other, and I thought they might like me too, but I wasn’t sure. After I’d waited for a long time, and really given them the chance to speak up first, if it still wasn’t happening, then I’d say something.


Because I really figured I had nothing to lose.


Sometimes it worked out, sometimes it didn’t. Sometimes I’d share my feelings, and they’d tell me that they liked me too, and then would explain why they’d been holding back. Sometimes I’d tell them how I felt, and they’d tell me that they had feelings for me too, but that they weren’t going to pursue it. (That’s a hard scenario, because you know they like you too, but it’s not going to work out. It’s a tough one to move on from.) And sometimes they’d tell me that they didn’t have feelings for me, and that hurt tremendously. But… at least I knew.


So friend, if you have feelings for someone today and are wondering if you should say something, here are the 5 things I would say you should consider:

1. Consider the amount of time you’ve known each other/have been waiting

The thing I don’t want any of us to do is to speak up too soon. Sometimes when we speak up after a short period of time, we can run the risk of coming on too strong. We’ve seen that happen the opposite way, haven’t we? Maybe it’s happened to us, or to a girlfriend of ours. A guy came up to my best friend one time after having just met her, and he told her that he really liked her, and wanted to intentionally pursue her towards a serious relationship.


Yikes! Right? She didn’t know anything about him, and now she felt the pressure to know whether he was the one or not, almost instantly. He didn’t give her the time to get to know him, and to do so casually. He put a lot of pressure on it immediately, asking her to know something she wasn’t ready to know. So she backed away and said no.


This happens, I think, when we come on a bit too strong.


Give yourself and this guy some time to get to know each other. (I’ll teach you lots of ways to do that in low pressure situations in the course!) Make sure he’s had time to form an opinion about you, to figure out if he likes you, before you say anything.


But also, don’t wait too long.


Sometimes I hear from girls who have been in this confusing, convoluted waiting pattern with a guy for years, and sweet friend — it doesn’t have to go on that long. That’s just torture! Because really, they shouldn’t need 2 years to figure out whether or not they like you. After that long, they need to have an opinion. You are you, take it or leave it. You know?


There’s not a perfect amount of time, and it totally depends how often you see each other in this amount of time, or how much time you’ve gotten to spend together. But I’d say no more than 6 months, and no less than 3 — as a general rule.


If you’re in that window, if you’ve gotten to know someone, if you’ve had time with them where you feel like they’ve gotten to know you, and it’s been more than a few months, I think you can say something!


If you’ve been in this holding pattern with a guy for longer than 6 months, sweet friend, I think it’s time to say something.


Because even if the answer isn’t the one you want to hear, at least it’s an answer. You can stop wondering, and start freeing your heart up for someone who DOES know that they like you! You deserve nothing less than that.

2. Consider the possible responses you might receive 

The truth is, you might not receive the answer you’re hoping for.


You may tell this guy that you have feelings for him, and he may tell you that he only sees you as a friend. That’s totally possible, like, really possible.


But, even if that happens, I think that’s still a good thing. Because again — being hung up on someone is really, really hard.


I once had someone I was hung up on say that having crushes are fun. I wanted to pop him in the face right then and there, because the feelings I was wrestling with, the waiting, the wondering and all for him? That was not fun. Not for a second.


And so if you do tell this person how you feel, and they don’t respond with, “I feel the same way! I was just too scared to say something! Want to go on a date?” at least you know.


You know the truth, and you can start to move on.


When we have feelings for someone, even if they’re not reciprocated, our heart is occupied, making it really hard for us to develop feelings for someone else.


So if this guy isn’t going to take the place in your heart that you so generosity reserved for him, you need to free it up so that someone more worthy can.


Does that make sense?


So as you’re thinking about doing this — as you’re thinking about telling this person how you feel, consider all of the responses you might receive, and really be aware that any of them can happen.


But know that even hard truth is good truth, because it helps you move on to something even better.

3. Consider how to tell him

This is the hard part, isn’t it? The actually telling? How in the world do you muster up the courage to say something like this to someone who probably already makes your stomach do backflips just by hearing his name?

Here are a few tricks I learned (from experience of course!):

a. It doesn’t have to be perfect

I think a lot of us shy away from hard conversations because we’re afraid what we have to say wont come out perfectly. And I hate to tell you, but it wont. No matter how long you wait, or how much you practice, a conversation like this probably isn’t going to be your smoothest moment.


I know it wasn’t for me.


But know that that’s okay. If the guy is kind at all, he will totally give you grace for your nerves. And if he has a pulse, he’ll understand that you’re totally nervous because he’s had moments like these too.


So just be honest about how nervous you are, and do your best to tell the truth anyway. It’s okay if your voice shakes. It’s just part of it. But don’t wait until you think you can do it perfectly. This is a nerve-wracking, imperfect thing, and that’s totally okay.

b. Don’t do this over text

I don't know about you, but the vast majority of my communication with people these days happens over text. I love texting. It’s convenient, doesn’t require you to step out of the room for an hour for a phone call, it’s way more relaxed than scheduling a coffee date with someone, it’s just easy!


But I will say that while it’s the easiest way, texting is definitely not the BEST way to have this conversation.


Texting, email, Facebook messages, because there’s no voice inflection, no face-to-face connection, it’s the most fertile ground for miscommunications. You don’t know what the person’s tone is, you aren’t able to ask follow-up questions, there’s less accountability, so sometimes we’re not as kind, it’s just not the best way to have this conversation.


I had a girlfriend tell a guy that she liked him over a Facebook message one time, and what she didn’t know is that he was in the middle of nowhere for weeks, and didn’t have service or wifi, and so he didn’t respond for almost a month! She was totally freaking out because she thought his silence meant he didn’t like her. Well, eventually he did write back, he liked her too, and they’re married and just had their first baby! So it worked out. But she would have saved a month of worry by just having the conversation over the phone or face-to-face.


And so, as hard as it is, I would say that face-to-face is the very best. Ask him if you can go get coffee, or if you can step outside together, or if you can go on a quick walk.


Second best is the phone, or Skype if you’re not in the same place.


I will never ever forget how much my hands were shaking as I held the phone to my ear to have one of these conversations, but I’m so glad I did it. And SO glad I didn’t do it over text.


Just trust me on this one. Yes, it takes world’s more courage, but the clarity, truth, connection, and resolution is so much greater when you’re actually talking to each other, instead of typing the words on a screen.

c. Say everything you want to say

I’m totally not advocating for a giant spill of how much you think about him, and how many times you’ve actually doodled his name in your journal. But I am advocating for using this moment to say everything you have to say.


This is your moment, you’ve already worked up so much courage to have this conversation, you may not get another one like it, and so this is the moment to lay all of your cards out on the table.


It’s tempting to say, “I like you a little bit,” Or “I’m a little bit interested in hanging out sometimes.” But the last thing you want to do is to have to initiate this conversation all over again. So take this moment while you have it, and lay out your cards.


Again — you want to walk away knowing that you did everything you possibly could do to make this work. And if it still doesn’t, you can walk away and wash your hands of this knowing that at least you really tried.

d. Write it out first/practice

So while texting/email is not the best way to have this conversation, writing out your words is a great way to figure out what you want to say.


I’m much better at expressing myself when I have some time to think through it, when I have space to process, and the delete button to go back and try it all again.


So give yourself some time to really figure out what you want to say. Write it out, delete it, write it out again. Work on it for awhile until you feel like you really have the nuts and bolts of what you want to say figured out.


And after you do this, you’ll be so much better prepared to have the conversation.


Maybe I’m a total nerd, but I would even bring the piece of paper if you need it. Again — a kind human will totally have grace for what you’re about to do, and how nerve-wracking it is. So if you’re afraid of losing your words, write it out and bring it with you just to remind you in case you forget something!

4. Decide that you will really believe whatever he says in response  

So one of the tricky things I think can happen after we have a conversation like this is that sometimes I think we tend to not believe the answers they give us.


I know I for sure did that.


I’d muster up all of my courage, I’d lay my cards out on the table, they’d lay theirs out too, and I wouldn’t quite believe them.


Maybe they said that they like me but they’re not going to pursue anything with me.


I’d walk away elated that they have feelings for me, and pretty positive that they were going to change their mind about pursuing me. I’d keep holding on, keep believing what I wanted to believe. I wouldn’t believe the cards they’d laid out for me, and therefore I wasn’t in any better position to be able to move on.


Or maybe they’d say that they just see me as a friend, but they seemed nervous as they said it. So I’d walk away thinking, “He SAID he just sees me as a friend, but I think that means he likes me but was just too afraid to say so.”


So we still can’t move on.


This is a really hard thing for us to grasp onto, because it’s just not how we always operate as women.


Sometimes we say something, but we really do mean something else. But the thing I’ve found is that guys don’t do this quite as much.


My husband and I have this conversation all the time. He says one thing, but I read another, and after awhile of total miscommunication, he has to stop me and say, “Steph, I said this, and I actually meant it! I promise. I say what I mean.”


We’ve created this moment for truth-telling. We’ve pulled them aside, we’ve laid our cards out on the table, and we’ve asked them to do the same. And so we really have to believe the cards they lay out for us.


And even if — EVEN IF — he says something and he means something else, I think we should take them at their word and be surprised if something changes. Because I think it’s so much easier to grab on again than it is to let go.


When I told one guy how I felt, and he told me he liked me but wasn’t going to pursue me, I WISH I would have just believed him, because he really didn’t change his mind. But even if he had changed his mind, it would have taken me 4 seconds to change mine too, instead of the months and even years it took me to let go of the hope I was holding onto.


So, sweet friend, when you lay your cards out on the table, and he lays his out too, discipline your mind to believe him. Because that’s really the only way to move forward, and move on.

5. Consider having a girlfriend on call 

I have no idea how this conversation is going to go, and neither do you. And that’s why I think it’s so helpful to have a girlfriend on call to connect with after you leave or hang up from this conversation.


Your heart may be hurting, you may be totally elated, you may be totally shocked at what you hear, you may be disappointed. But regardless of what the response is, I think it’s so helpful to have someone to debrief with, someone to go get ice cream with, someone to talk to about what you just learned.


Having girlfriends on call is always a good idea. Right? So make sure you tell someone what you’re going to do, and make sure they’ll be available once you’re done.


Friend, I so wish we didn’t have to have this conversation today. I wish that every guy we liked, every guy we noticed and took an interest in was 3 steps ahead of us — totally aware of how great we are, and totally ready to ask us out.


But again with the batting average: Not every person we are interested in is going to feel it back, or be ready to express their feelings for us, not every relationship we attempt is going to work out, and that’s how it’s supposed to be.


And while this is really painful sometimes, and really hard to understand, it’s also really beautiful.


Because every relationship we have, every wonderful person we meet teaches us something, can bring us closer to the heart of God if we let them, can help us learn more about ourselves and what we’re looking for, and helps us in the process of elimination.


“Okay! It’s not you, so it’s somebody else!” And we can prepare our heart to meet a wonderful someone new.


So be bold friend, if you feel like it’s time for a conversation, I pray that you initiate it. And while I pray that everyone you meet knows how deeply wonderful you are, if this person isn’t it, then I pray that this conversation helps your heart let go so you can meet the person who is.


Have you ever found yourself in this situation? I'd love to hear your story and how this resonates with you! Pop your thoughts in the comments below!

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