Today’s article is in response to a question from a reader (via Ask Melissa!) about how to decide how long to wait for someone you’re in a relationship with to figure out what he wants. In my response, I provide guidance on how to approach this question, including what you need to know to decide how long to wait, what you should do if he is making progress in your relationship but not at the pace that you would like, and when waiting is actually a good thing for you and your relationship.
I am 41-year-old with no kids and have never been married. My boyfriend is 46 years old. He has two sons 10 and 13 years old, and he was married for 12 years, officially divorced in June 2017. He hasn’t lived with his wife since September 2015. His wife cheated on him with his best friend. We met in September 2016. We don’t live together.
I met his sons very briefly in January, and he introduced me to them by my name. We never discussed the status of our relationship. But by the look of it, it’s exclusive, although it’s been a year and we are not moving any further. He is busy. I am busy. But I can always make time to see him.
He knows I want to have a family and kids. He accepts that. However, he had vasectomy, I told him that I will have kids whether he wants it or not by choosing a donor. He admitted he would like to have daughter but not for the next two to four years. He doesn’t mind if the kid is from a donor. I asked him before his divorce if he will need some time to be free. He said “no, I had enough fun before marriage.” That’s it, we didn’t discuss anything else.
I want to know if it is worth spending my time with the man, as I am very attached to him. I want to know how much longer should I wait before he decides what he wants to do. I want clarity. I don’t know if I can ask him all the questions now or wait. I don’t want to miss what is out there for me as I am not that young.
-Restless in London
Dear Restless in London,
I hear your concern. And I can understand why you might be feeling torn and seeking answers.
You’re certainly not alone in your desire for clarity around how long you should wait for him to figure out what he wants. It’s one of the most common questions that I get.
“How do I know if it’s worth spending time with this man? How long should I wait for him to figure out what he wants to do?”
I especially noticed a few phrases in your message:
“We never discussed the status of our relationship.”
“…we didn’t discuss anything else.”
“I don’t know if I can ask him all the questions now or wait.”
It’s clear that what’s missing here is clarity about the status and future of the relationship.
But I also wonder: What is in the way of discussing what you really want to discuss with him?
Because to make conscious decisions about your relationship and to explore whether it’s worth spending time with this man, you need information.
And you get that information through your experience with him and through talking with him—and also through having a deep knowing of what you really want.
You’ve been seeing each other for a year, are exclusive, and are considering the next step (or at least one of you is).
It’s entirely appropriate at this stage of your relationship to ask him the questions you’ve been wanting to ask him.
You have every right to ask him about his plans for the future.
Sometimes we’re afraid to talk about our dreams or assert our needs in our relationship because we’re unsure how he’ll respond.
It feels risky because we’re afraid of pushing him away if we tell him how we feel.
But think about what is at stake.
You have a vision for the kind of life and relationship that you really want, such as wanting to have children of your own and sharing that experience with someone who will celebrate and support that vision.
But that vision is being delayed because you’re waiting for him to make up his mind on whether he wants to share this journey with you.
So, the sooner you get that information about the status of the relationship, the sooner you can make an informed decision about whether this relationship is worth staying in for you.
Or do you really need that information?
You always have the choice to take the information that you already have AS IS and decide based on THAT.
But ultimately it comes down to considering what’s most important to you in terms of the decisions in front of you.
What You Need to Know to Decide How Long to Wait
You wouldn’t be questioning the long-term viability of your relationship if you were entirely content and hopeful about it.
So, I’m guessing there might be other issues in your relationship, other than being unclear about where your boyfriend stands, that are causing you to wonder whether it is worth it to stay.
But at a minimum, you want to find out:
How clear is his vision for the kind of life and relationship that he wants? Is it “I don’t know what I want”? Or is it “I know want to marry you some day, have kids with you, buy a house, travel to Paris…” How clear is his vision?
How ready is he for the kind of life and relationship that you really want? Because even if he is clear on what he wants, being ready for it is another thing entirely.
He might want to build a life with you, but if there are things interfering with his readiness to move forward with you, whether it’s legal, financial, or emotional, that should get factored into your decision-making as well.
How committed is he to achieving his vision? What meaningful action is he taking to achieve what he really wants?
It’s one thing to dream about it and talk about it.
But what really matters is ACTION.
Is if he is treating it like a goal and taking meaningful strides to reaching that goal?
If it’s still “pie in the sky” and he doesn’t know what he wants or he’s not taking meaningful action to achieve it, you could be waiting indefinitely.
In this case, I would say you are better off moving on.
Because if he doesn’t know what he wants, then there’s no destination in sight.
And how can you get anywhere if you don’t know where you’re going?
What is the OPPORTUNITY COST of staying in the relationship and waiting for him to figure things out? While you’re in a relationship with him and he’s “figuring things out,” some of your needs aren’t being met and maybe some of the vision you have for the kind of life and relationship that you want isn’t being realized.
For example, if getting married is part of your vision and he’s unsure if he wants to commit or unsure when he will be ready to commit, then the opportunity cost of staying in this relationship (while you’re waiting for him to figure things out or waiting for him to be ready) is otherwise being in a committed relationship or dating someone who is ready to be in a committed relationship.
It is costing you other opportunities that are important to you.
But that isn’t necessarily a bad thing (I explain later). You are also getting a lot from being in this relationship.
You said you’re very attached to him.
You have a connection to him that’s very meaningful to you, otherwise you wouldn’t be attached.
So how long do you wait for him to figure things out?
This is a deeply personal decision.
You have to look deep within yourself and decide just how important those other opportunities are to you.
What are those other opportunities really worth to you?
How important are those other opportunities to your happiness?
How time-sensitive are those opportunities?
The line in the sand is different for everyone.
Therefore, it’s so important to get clear on your own relationship requirements (your deal breakers; what you require in a relationship in order for the relationship to work for you).
What If He IS Making Progress toward Your Shared Dreams but Too Slowly
That can make the decision to stay or go even more difficult because it feels like you’re making progress in your relationship, but you’re just not there yet.
Yes, you’re moving. You’re making progress.
But you’re still not at your destination.
You’re still “waiting.”
And your waiting comes as a price.
It comes at an opportunity cost.
So, if this is happening in your relationship encourage you to ask yourself: At which point would you no longer be willing to wait?
At which point would the opportunity cost of waiting be too high for you to justify staying in the relationship?
In my view, it is MORE important that you get clear on what you truly want and how YOU want to live your life, than it is for you to get clear on how HE wants to live his life.
You’re not in charge of what information you’re given.
You can only ask questions and have experiences and hope that you get the answers that you need.
You can only make decisions based on what’s true for YOU.
At the end of the day, you’re in charge of what happens in your life, he isn’t.
So, if your future and happiness is hinging on SOMEONE ELSE doing something, you’ve given your power away.
The truth is, you’re in charge of your own happiness.
You own your decisions.
And the more certain you are about what you want, and the clearer you are about the life you want to live and the values you want to live by, the easier it will be for you to discern whether he fits into your vision.
Could Waiting Be a Good Thing? It Depends.
But it’s not all about the destination
What about the journey to achieving your vision?
When might “waiting,” or (temporarily) denying parts of your vision, actually serve your long-term happiness?
It’s when “waiting” is PART of your vision, not to the exclusion of it.
About three years into my marriage I went to a bookstore event that was hosting of one of my favorite travel bloggers.
He was talking about the newest edition of his book about how to travel around the world for cheap.
He talked about travel, blogging, and all the amazing places that he’s been too.
And all the amazing places that he’s planning to go to.
I had stars in my eyes.
A wistful feeling took over me.
And then a sadness and disappointment.
Worldwide travel and adventure is not the life that I ultimately chose.
I wondered for a moment—actually for a few days—”Did I make the right choice?”
I had always been a free spirit. I still am.
I had considered a life of writing and travel.
Even had some success in it when I earned some bylines in several regional and national lifestyle magazines.
This was before the genre of travel blogging had really taken off on the internet.
But you know the story.
I got married.
I don’t have a career as a travel blogger.
And these days whenever I travel it’s to visit the in-laws.
Come to think of it, I actually haven’t used my passport in over 5 years.
So, to tell you the truth, in the days after that bookstore event I felt down.
I wondered whether I had denied too much of myself.
I have many loves. And travel is one of them. Travel is a big one.
But marrying someone whose job doesn’t allow him to telecommute, and who has daughters who are still in grade school and who need their father, is incongruent with my dream for worldwide travel, at least for the immediate future.
Did I settle?
A new awareness came to me when I was thinking about my vision for my life.
Sure, I really want to live a life of travel.
Adventure and freedom is something that’s very important to me and my sense of fulfillment in life.
But so is sharing life with my husband and my family.
So, are these two visions mutually exclusive?
Yes and no.
I can’t travel around the world right now for extended periods of time, unless I want to do so without my family.
But if I look deep down, I don’t really want to travel around the world right now if it means being away from my family.
Yes, it’s part of my vision for the kind of life that I want. But it’s not part of my immediate vision.
It’s not a requirement for me that I travel right now.
It’s more important to me and my happiness that I spend time with the people that I love, and not necessarily travel around the world.
In fact, what I would LOVE is to be able to share in those travel experiences—share the experience of freedom and adventure—with the people I love.
And so maybe that doesn’t happen until we’re both retired empty-nesters. That’s fine with me.
But when I look deep down, the two visions of worldwide travel and spending time with people that I love aren’t really at odds with each other.
The waiting to travel is part of my vision, not to the exclusion of it.
Because while I’m not traveling, I’m spending time with my family.
And spending time with my family IS a part of my vision.
Traveling with them is a part of my vision.
So, I didn’t settle.
I’m not actually denying my dream if I’m proactively choosing something that I want.
Because waiting and the delaying worldwide travel, is actually PART OF and IN SERVICE TO the bigger dream.
In other words, you’re not settling if you’re making conscious choices on purpose.
You’re not settling if you’re living life ON PURPOSE.
So, I encourage you to ask yourself, if you feel torn between two desires, are those desires mutually exclusive?
Or could they support each other?
Or if you are indeed denying part of your dream, how important is that dream to you and how time-sensitive is that dream?
You mentioned that part of your dream is to have children of your own.
So, including that time-sensitive factor in your decision-making is important, too.
It can feel like a no-win situation.
But I invite you to look at it a different way.
What if it wasn’t about choosing between “two bad decisions,” but rather choosing between OPPORTUNITIES.
And about prioritizing which opportunities are most important and meaningful to you.
You’re not losing in either case, in whichever path you decide to take.
By saying no to some things, you’re giving space and opportunity in your life to experience other things.
The key is in determining which experiences and opportunities are most important to your sense of fulfillment in life.
Dating a Divorced or Separated Man and Need Personalized Relationship Help?
All relationship situations are different, especially if you’re involved with a separated or divorced man. There are complexities you may not have dealt with before in a dating situation. His kids. His ex. His marital status. And all the drama in between.
How do you overcome the dreaded “waiting”?
Does HE lack boundaries with his ex and kids, or are YOU the one who’s being intolerant?
How do you get him to prioritize you and your relationship??
I totally feel you. I’ve been in the same boat. I’ve dated my share of separated and divorced men back in the day.
And…I’m happily married to and have kids of my own with one, too!
If you’re feeling stuck, confused, or frustrated in your relationship and want personalized solutions, I can help.
If you’re suffering, you don’t have to continue suffering. I promise. Sometimes you just don’t know what you don’t know. Let’s talk about how to overcome the relationship challenges you’re facing.
In a private 1-on-1 Relationship Clarity Session, you’ll get personalized dating and relationship help for your specific dating issue so that you can successfully navigate the complexities of dating a divorced man and know exactly what you’re getting into, overcome the challenges, and consciously create the deeply fulfilling relationship you want!
Ready to improve your relationship and overall happiness? Click the button below to get all the details, view my calendar (I usually have some openings every week), and conveniently book a session:
How to Decide if He’s Right for You
Download my free Relationship Choice Assessment to help you get started. In my free guide you’ll discover:
- 30 questions to ask yourself to help you decide if you should give him a chance or if you’re wasting your time
- 22 red flags you should be aware of if you want to avoid heartbreak and painful surprises
- How to assess your compatibility with your partner to know if your relationship has long-term potential
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