How To Wait For a Woman Who Isn’t Ready

 2 years ago
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How To Wait For a Woman Who Isn’t Ready

Maybe now is not the time to be her boyfriend, maybe it’s the time to be her “what-if.”

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By Chelsea Leigh Trescott

Dear Chelsea,

I’m in a place I’ve never been with a woman before and I’m looking for some insight! Let me explain.

I’m a 28 year old father of two, a 6 year old girl and a 3 year old boy. I’ve been single for just over a year now. Spent a significant amount of time healing from separating with their mother and then a failed relationship afterwards. I decided I was ready to try and meet someone and with a little encouragement, messaged a girl that caught my eye on Facebook. We were mutual friends that met through an ex and I’d found myself noticing her photographs more and more. We had a nice connection right from the start and I could tell she was someone that I wanted to meet and get to know. I asked her on a date and she said she’d think about it (she being recently single herself). After a few days of more talking she let me know she was coming home and wanted to grab a drink with me. She’s from my town but lives an hour away.

First date was fantastic. Everything went as a perfect first date is envisioned to be. We had great conversation, were both very in tune with one another, had a lot in common, and shared a very palpable physical attraction. We ended up hooking up in her car at 4am. (Yes, possibly not the best move but hey!) It was clear we wanted to see more of one another and so the following weekend she was back again. Things couldn’t have been going better!

I ended up going to visit her the following week and she asked me to stay with her. Everything still progressing as you’d like it to. Then, quite abruptly, she confronted me with the kicker. She revealed to me that she was feeling that she wasn’t quite ready for me. Despite recognizing me as a wonderful person and thinking things were going well between us, she had an incident with the ex while trying to retrieve some leftover belongings and recognized that she was still allowing him to affect her emotionally. She wanted to take some space out of fear that this would jeopardize us. I only found that this made me more attracted to her! Finally! Someone mature enough to identify something about themselves and want to deal with it positively. This was great I thought, I can handle this. She’s told me I’m wonderful and to let space attract her to me more while she dealt with herself and healed.

That never happened. Within a day or two she was asking me to come see her. I obliged (was this my mistake?) It’s hard to say no when you want something even if you know it’s probably not the best for the other person. I had encouraged her to do what she felt was right and this was it. She wanted me around! For another week everything was back as it had been. We connected more and more. Found ourselves getting closer and closer. Then it happened again. The ex contacted her about wanting some things back as well and was ugly and hurt her again. Back to the space. Back to withdrawing from me. All the while I received encouraging words that I was still great and left a big impression and that I am a lot of what she wants. Just to trust her and give her space and let her come to me. She likes the chase you see, and I made myself very readily available to her.

So here’s my question. It’s been a week and a half now. I’ve received some Snapchats, some messages that she’s thinking of me and hopes I have a good week. But every time I reply to them, she says nothing. Give me some insight into what could be going on with her. Should I be playing harder to get and not replying to her? It’s not in my nature to ignore someone but she rarely replies after contacting me. She always comes off as incredibly straightforward and genuine so I have no reason to believe she’s letting me off easy. I think she genuinely wants to heal and give us a chance. I don’t contact her at all, I only reply when she does. I’m really into her and I’m content to bide my time as I’m not desperate to find something else.

I’d love some advice. This is a first for me. Usually it’s cut and dry, when it’s over it’s over. This feels different but I’m driving myself a bit crazy wondering how long she’s going to take!


Guy playing the waiting game

Dear Guy Playing The Waiting Game,

Letters like this and questions like yours standout to me. You sound so tame, sincere, so sensible. You sound ready. And yet, something is keeping you from love.

It’s easy to read your letter and focus on your love interest being the culprit, on this woman who calls you wonderful and says that you are a lot of what she wants but then brings her ex into the equation and retreats. It’s easy to get swept up in the story, in you being this man who’s doing exactly what women say does not happen for them enough.

WTF?! How is she not with you?

Your connection sounds so good!

Reading your letter one, two, three times, my reaction is you’re doing all the right things. My God, you’ve even got me rooting for you. I mean, what’s not to love?

  • You’re listening.
  • You’re respecting her boundaries.
  • You’re approaching this relationship with patience and perspective.
  • You’re encouraging her to heal.
  • You’re even letting her lead.


What impresses me most is the ease in which you seem to accept her. Let’s be real, most of us would internally combust if an ex was mentioned. Not you. You accept this woman. You accept where she is. You accept where she isn’t. I imagine that this is because you naturally default to empathy. You’re giving her space because you can remember how badly you’ve needed that once for yourself and, seeing where that’s gotten you now, you know firsthand that space and time can work wonders.

But then, I read your letter again and I think about you some more and suddenly I see, that for all your acceptance, what you aren’t accepting is her words.

She told you she doesn’t feel ready for you. Why won’t you believe her?

This is why you and your letter standout to me. Because I’ve seen myself and countless other romantics in you and your predicament.

We don’t accept what we know.

We think we can change someone’s mind.

When it comes to relationships, we resist what we’re told and let our hearts run wild with what we think instead.

In short, we prefer interpretations to answers. (Though beg for answers, we do.) It’s our way of holding on to a vision and all the desires we have informing it rather than accept that we cannot (yet) have what we are after. The trouble is, our interpretations of reality fool us and can drive us crazy in ways that answers never will. Because answers are meant to provide us peace of mind.

I want to remind you of the answers she’s already given you, because in your letter I spot a lot of them, and I want you to hear them this time. Then, ask yourself why her honesty isn’t providing you with enough peace.

If I had to guess, I’d say it’s because when she tells you to let her come to you, I think you don’t trust that she will. You think that if time comes between you, you’ll be history, so to speak, just a blip in the past. This thinking is pretty normal. That’s why they say, “the good ones always get away,” right?

It’s normal to fear that time apart will enable someone to move on from us. The best you can do is trust that it won’t.

It’s important to remember that if you’re meant to be together, nothing can stop that from happening. Except, of course, force. Forcing the relationship to happen by insisting you commit to each other sooner than maybe you should, or insisting you know where this relationship is headed, will likely jeopardize your chances together. The good news is she gets this. From what you’ve told me, she’s aware that rushing into a relationship often jeopardizes it. She even said she was afraid of that.

Are you hearing this?

She doesn’t want to ruin her chances with you.

Believe her.

My starting advice is to take your time with this woman. If you’re able to go with the flow just a little bit more, you might find that the time and space she wants is ultimately the blessing this relationship deserves. And anyway, I can’t imagine time wouldn’t ultimately tighten your bond should you end up together or strengthen you individually. Either is a win.

Speaking of wins, I think it’s important to check in with yourself along the way and ask, “What am I gaining from this?”

I don’t mean that in a condescending if you’re not getting love get out kind of way. I’m encouraging you to look for what you might be getting from this relationship other than reciprocated affection. I’m saying check in and ask yourself,

“What am I learning to do?”

“How am I being stretched?”

Maybe right now this relationship is teaching you patience or challenging you to trust that someone will return. Reach below the surface and bring these smaller gems to light. They are just as valuable.

The truth is, sometimes the act of learning is far more transformative than the hunt we’re on for love.

This relationship might not develop in the ways you currently wish but that doesn’t keep it from being impactful. I’ll never forget meeting this man after my own long and “failed” relationship. Everything inside of me told me to go after him, to not let our meeting slip into one of casualty. I have never been moved — pulled, pushed — so invisibly toward someone like that before, and I’ve never honored my intuition as I did then either. He was gold. Magic. He was like no one I had ever known. He brought out the boldness in me, my own blind faith and dormant adventure.

Did I want him to be the one?

Did I feel like he could be the one?

Of course I did. Only, that want and those feelings weren’t mutual.

It would have been easy to pass this off as a failed attempt at discovering love. It would have been easy to feel humiliated, rejected, and let down. And yet, I didn’t feel much of that at all. I still felt thankful for him. I still felt open. I felt like I didn’t need this man to love me, I needed him to just let me know him.

Why? Because I knew he had more to teach me.

I knew that having him in one way and not having him in another would expose me to something vital about myself, and the bravest part of me told me I needed that.

I needed to lean into an uncertain relationship to confront an uncomfortable truth that would help me expand.

At the time, my mother told me that sometimes people are brought into our lives as a catalyst, not always as an answer.

My mom was right.

The man I met was not the answer I so wanted him to be but what knowing him has taught me is that sometimes a catalyst is the greater of the two.

Maybe this woman is your catalyst.

Maybe she’s in your life to show you how dedicated you are ready to be. That’s worth realizing, right?

I’m of the opinion that it’s in the midst of romantic tension that we often see ourselves most clearly. So, the inconsistency of a woman you’re always willing to show up for makes you realize how grounded you are in your own heart, how prepared you are to be the person you say you can be.

The tension I pick up on in your letter is simple: an available man is trying to date an unavailable woman.

You can go all in but she can’t help but hold herself back.

This is why you’re at standstill.

This is why your communication is clashing.

I’ve already emphasized that she’s not ready for you and, ultimately, because you’ve told me this, I know you know that, even if desire is urging you to overlook it. I’m guessing what boggles your mind is why her actions don’t match her words, why she reaches out with a message and then disappears. I get the feeling you don’t understand and can’t relate to the kind of self-control she is demonstrating, the way she’s able to be all about you and, then, just as capable of keeping herself from you.

This just isn’t the way we expect women to act. When a man demonstrates his readiness, we expect a woman to leap, cling, and commit herself.

Ah, welcome to the new age.

It probably feels like she runs hot and cold but, on the outside looking in, I can tell you that to me nothing suggests she’s unsure about her feelings toward you. In fact, and it may be difficult to hear this, I don’t believe her feelings toward you are what’s predominately driving her actions in the first place.

(In my opinion, it’s her unavailability and her fallout with her ex. More on that soon.)

What this means is, had you shown less interest or more interest in a different way, that wouldn’t have changed where you are at with her now.

The peace of mind I’m offering you here is, don’t question anything you’ve done. Don’t think back on the choices you’ve made and wonder if, had you done things differently, you’d be further along with her or be more desirable in her eyes. You’ve acted honestly. Good relationships can’t be built on anything but that. If everything you’ve told me is true, then, you’ve done the right thing and, if anything, it’s because you are desirable in her eyes that she keeps pressing play then pause, play then pause.

Women complain about men doing this all the time. And, guess what? Women are capable of waffling, too. They, too, get scared of committing to the real deal.

(It’s very possible that you feel like the real deal to her, or at least like a man who would want a woman whose broken pieces have been put back together.)

I see it all the time, and I see it especially in women who talk about how ready they are for true love. You send a man over who can give her that, and she will find every reason to overlook him or doubt his intentions, jeopardizing the relationship completely.

Basically, just like men, women try to buy themselves more time before committing. The only difference is, women very rarely see this in themselves, let alone accept it enough to acknowledge it outright. Instead, you’ll just see a woman keep going back to her ex or fall into relationships with unreasonable partners. Serial monogamists, bouncing from relationship to relationship, are guilty of being commitaphobes, too.

This is exactly why you should want/insist on her doing her own thing before dating you. You don’t want to be a reaction to the last guy. You want her to date you because she’s thinking clearly, knows what she wants, and isn’t looking back.

As an available man, you do not want to be in a relationship with an unavailable woman because, believe me, she will sabotage it.* And listen, you cannot change this about her either or inspire her to be different for you. Every single person must grow at their own rate. If you encourage her into something she’s not ready for, she’ll only resent you. And women are good that.

So, if she’s not ready, why is she still reaching out to you?

Because, just like you don’t want to see her disappear, she doesn’t want to see you disappear.

What do I think is going on with her when she sends you a message and then won’t reply back?

I think it’s a way of keeping you on the hook, of showing up in your life because she does want to be in it, but then backing away because anything more would pull her — and you — in too much. And, like she said, she isn’t ready for that.

I think she says she can’t see you but then, a few days later, has to see you because that’s just how desire works.

Putting words to what is best for us is the easy part but to actually do what is best is much more difficult.

  • None of us really want to put in the work of healing ourselves, we just want to be ready to move on.
  • None of us really want to keep ourselves from someone, we want to see them and prove we can handle it.
  • None of us want to sit in the discomfort of not knowing if someone will be there when we’re finally ready for them, we want to see them now and hold them now and reach out with a Snapchat so they won’t forget us and leave our lives.

She doesn’t respond because your response relieves her, and that’s what she’s looking for: the confirmation that you still care.

Basically, any inconsistency between our words and our actions happens because we want to feed the fantasy as we wait with hope.

As for what you should do while you are waiting for her, my advice is to live but not to live in wait. This doesn’t mean you have to be out there dating, it just means continue to be available to opportunities that encourage you to put yourself out there and take chances. Scan your Facebook and connect with more people. Or, just walk out into the world. Enjoy your daughter and your son. (Congratulations on being a daddy, by the way.) Document their lives. Read good books. Find ways to smile and, above all, be open to more catalysts and answers arriving for you.

Do not, by any means, begin playing hard to get. Ignoring someone breaks hearts, it never breeds love. You’re an evolved human being, don’t regress for anyone.

If you begin driving yourself crazy again, remember that you are proof that love and healing is a journey that takes time. Consider how she may need a failed relationship after this ex of hers, just as you needed yours after separating from the mother of your children. If you don’t want to be her failed relationship, give her space and insist she do what she told you she must do: heal.

Your advantage in all this is, no man comes in and out of a woman’s thoughts like the man who could have been.

Maybe now is not the time to be her boyfriend, maybe it’s the time to be her “what-if.”



PS: Don’t hold yourself back from reaching out first. If this relationship is ever going to work, you have to do you. She has to fall for you, for your instincts and your initiatives. One of my favorite gestures is receiving a text or an email from a man I’m dating or who is simply a friend with a link to a song or an article or a picture they’ve snapped. There doesn’t need to even be anything more than a link and a line like this made me think of you. Something as simple as that is an immediate pick me up and it makes any guy both thoughtful and intriguing to me. All women want to feel thought of and understood. You can’t go wrong with making it lightly known.

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