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High Stakes Dating

June 7, 2012

I saw a young woman in the elevator the other day. In her arms, she lightly bounced a newborn baby. I told her that her baby was beautiful and asked how old he was. She replied that he was just three weeks old.

“Your first?” I asked.

“No, my fourth,” was her reply.

I was surprised. When I say she looked young , I mean she looked around my age. Certainly not old enough to have four kids. “Wow! You look so young; I never would have thought you could have four kids!”

“I mean, I am 28.” Her tone basically said, “I am so old, of course I have four kids.”

I’m only a half a year away from 28.


poker chips

Gone are the days of dating for fun. This is for keeps. Photo courtesy of Viri G

At some point, if you are a person who wants to get married and have children someday, you enter this phase I am calling “High Stakes Dating.”

It happens to different people at different times. For me, it happened somewhere right after I turned 27. Suddenly, every decision I make is crucial. Every month I stay with someone is a commitment to the future.

Gone are the days of “just having fun” or “seeing where this is going.” No longer can you stay with someone unless you can see yourself marrying him or her. And when you break someone’s heart, or they break yours, the stakes are different.

They are higher.

Maybe you date someone for a year, and then realize they aren’t for you. Well you just took away a year of this person’s life in which they could have found someone else. Gone is a year of your fertility (particularly if you are a woman). Gone are all those guys who were single a year ago, and have been snatched off the market while you were wasting your time with the wrong guy.

Most days, I don’t let this kind of thinking get to me. But then I see a 28-year-old on the elevator who has four kids.

Things have been going great with Chef. He makes me incredibly happy. I could not ask for a more caring, attentive man. We have a lot of fun together and I love being with him.

But then ask me how long we’ve been together, and I get a little panicky. It will be two years this summer since our first date.

And I think he wants to marry me.

Okay, I don’t think. I know. He’s said it.

Chef’s apartment complex is being demolished in September, so he needs to move. We’ve been talking about him possibly moving in with me. He’d like to use the opportunity to save money to buy me a ring.

He doesn’t want to move in with me unless we are planning to spend the rest of our lives together. He’s learned from his past and says he doesn’t want to move in with someone casually ever again.

I, however, am in the other camp. With my ex, I insisted that we get engaged before we moved in together. And then, when living together revealed the truth about him, I vowed to live with a guy before I committed to marrying him.

I love Chef. I’m certain he’d be a great husband and father. But something is holding me back.

I’m scared for everything to change. I’m worried about making a mistake. I don’t trust my own instincts. Scratch that, my instincts are all over the place. I truly don’t know what I want to do.

When did life get so complicated?

When did I become an adult?

Why can’t there be a test drive for living together? Or for getting married, for that fact?

Why is every decision so critical? When did the stakes get so high?

Chef has been feeling some of the same emotions as me. While I think he’s less commitment-phobic, he’s also somewhat uncertain about the next steps in our relationship. We’ve decided that we should make a decision by the end of July. Which should be interesting, considering my sister’s baby is due just around then. A new baby could have an interesting impact on my emotional well-being.

I asked advice of my happily married friend. “At some point, you just make a choice,” she said. “You decide that this is the person you are going to commit your life to. And then when you have a family, you commit your life to the family. You don’t worry about if there are others for you. You’ve chosen a life with him.”

I jokingly told Chef I would poll my readers on whether we should move in together. You should have seen his face. Clearly, this is not a decision I should ask you to make for me (although that would probably make my life a lot easier!).

But do you have any advice for how to make the decision? How do you know what’s right?

Is there anyone out there experiencing High Stakes Dating?

Can anyone recommend a good life coach?

Copyright 2012. Simply Solo blog by Catherine Gryp. All Rights Reserved.

39 Comments leave one →
  1. Kelly permalink
    June 7, 2012 9:58 am

    Look at me; everyone told me at 17 I was to young to get married and they were probably right, but almost 24 years later and we are still together. I knew it was right for me granted I wondered sometimes if I knew what I was doing. Deep down I always knew it was the right thing for me. That is what you need to discover what is right for you and no previous instances or other persons can make that decision for you when they time comes it will be like a light bulb going off that says ” what I am waiting for”. You and only you can do that. Sure its good to ask advice from others but it doesn’t mean you have to follow it. If I had followed what everyone told me (and I so mean everyone) I would not have my 2 beautiful kids and my husband and I would have a totally differnt life and who knows what that life would have been it could have been this great experience, but I am perfectly happy with what I have and would not change it for the world. So I hope that you make a decision that YOU are happy with and that will lead you down a path in your life that one day you look back and say the same ” I would not change it for the world” Good luck we all have faith in you.

    Just as a side note we all like Chef he is a good man. Not to sway your judgement just a statement.

    • June 13, 2012 9:30 pm

      Thank you Kelly. It’s refreshing to hear someone say that the really believe in their decisions from so long ago. Too often you hear the opposite – people bemoaning the mistakes they’ve made. I’m so happy you are pleased with your life, and also that you like Chef. I’m lucky to have him 🙂

  2. June 7, 2012 10:05 am

    High stakes dating is right! Today is my 28th birthday and I feel like I’m living a high stakes life! Great post.

    • June 13, 2012 9:28 pm

      Happy belated birthday! 28 is gonna be a great year 🙂 Thanks for reading and commenting too.

  3. June 7, 2012 10:10 am

    Yeah. Um. So.

    I’m absolutely not the person to be weighing in. And yet I feel compelled, for some odd reason.

    Once your trust has been shaken to its core, there’s no way to know how to ever find firm footing — or even if firm footing in fact will ever exist again. I feel this every day. My boyfriend has been talking marriage for a while, and the thought makes me go weak with fear.

    And yet…

    I love him with all of my heart. I can’t imagine my life without him. I am totally, madly, deeply in love.

    Here’s the deal: I think accepting the idea of a future is in some way acknowledging the person you used to be, pre-betrayal (and with trust intact). And for me, I thought that girl was gone forever. When I think about Brett, though, the hearts and rainbows and unicorns come prancing through me head — if only for a bit.

    I never want to be a fool again, though. I never want to trust unconditionally — only to find it betrayed. I never want to be “that girl” again.

    So finding the place where you can trust is like finding the girl you were before … wiser, sharper, more jaded — but still there, somewhat believing in a happily ever after.

    You know the answer to your own dilemma, Catherine. Buried. Deep down. Next to the heart of the girl you used to be — the trusting heart that you thought was torn apart.

    Just keep digging…

    • June 8, 2012 12:23 pm

      Hear, Hear!!

    • June 13, 2012 9:28 pm

      Thanks for your comment Mikalee,
      Reading your story over the years, and comments like these, really make me feel much less alone. You just put into words in this comment some of the feelings I’ve had but I haven’t been able to put into words. “I never want to be a fool again…” I feel the exact same way. And maybe that’s part of the reason I’ve been hesitant. You’ve given me a lot to think about. Thanks for sharing your story with everyone – you’ve helped so many people!

  4. June 7, 2012 10:10 am

    Hi Catherine! Imagine your life, right now, without Chef. Imagine the future without Chef. If you feel like you just got kicked in the stomach while thinking about life without him— then you guys should probably move in together. (How’s that for Brittany logic? Haha!) By being afraid of love, (for which I totally don’t blame you…) you are shorting yourself on the possibilities of happiness. It will never happen if you don’t give it a shot. He seems like a class act, girl.

    • June 13, 2012 9:25 pm

      Thank you, The Fashion Sense. When I think of losing Chef I feel a little sick to my stomach. Not quite a kick but definitely uncomfortable. Part of the problem is that I see relationships as impermanent because that’s been my experience (they are impermanent till one is permament, right?)? So I have always kind of doubted this, without any real reason. I’m afraid I’ve never let myself go 100%. While I am not certain if we should move in together, I know I don’t want to lose him. He really is a good man.

  5. June 7, 2012 10:12 am

    I would first like to say congrats on getting to this stage of your relationship. Knowing how to move on to the next stage is a critical decision that does require some serious deep self introspection. I knew my husband was the one, so much so, that I tried to run the moment things got serious. I was still very young and worried that I hadn’t experienced enough. We had a real conversation about it and I realized after examining my motivations that I was afraid because he was not the kind of guy I imagined myself being with, not necessarily about his looks but because of who was and what I knew as a “normal relationship”. What I call my relationship DNA was all screwed up because of what I saw growing up in my house as a child. I had a terrible non existent relationship with my father that affected the way I dealt with men and it almost ruined my chances of what will be 10 years of happy marriage to my best friend. I had to break the bad cycles and stop sabotaging the good ones for the bad ones that I knew.

    I would suggest that you dig deep into your past, consider who was the strongest male influence in your life while growing up and figure out what kind of messaging you received about men and relationships. Understanding why you love the way you do can be the key to your fear of making a mistake.

    You may think your fear of moving on as because of your last terrible break up but it goes further back than that. Wasted time is the least of your worries if you end up sabotaging yourself in the end. If you like him, want to be around him all the time, enjoy his company and he wants to do the same with you, then make the move, not because we’re suggesting it, but because its what you want to do despite your fears.

  6. June 7, 2012 11:06 am

    First of all, congrats on getting to this stage of your relationship. Its time to make decisions that could affect the rest of your life. Scary, but exciting!
    I feel your trepidation. Years ago, when I started dating my husband, the moment I saw how serious it was, I tried to run. I was young and feared that I’d be missing out on something or someone else better. We had a real conversation about it and through deep self introspection, I discovered that it wasn’t a fear of what I’d be missing out on, but that I was afraid of the relationship itself. My, what I call, relationship DNA was all screwed up. Everything I knew and learned about relationships was from my parents. My father and I had a terrible and almost non existent relationship which affected my perception of men and what I thought love was.  I was what I call, an actress, one of five rDNA profiles. Drama rules our world and if we don’t have that in our relationships, we don’t feel comfortable. Something feels off. 
    So while I went from bad relationship to bad relationship, dated jerk after jerk, I thought I was just unlucky. But then, I finally found a good one and I tried to run. 
    Next year will be my 10th year anniversary (I’m only 31!) to my best friend. If he had let me go I’d probably still be on track to repeating those same patterns of sabotage, seeking out co-stars to support my need for drama. It’s all knew.

    You might be thinking that your fear of making a move comes from your last failed relationship, but that’s a red herring. I would suggest that you look at the relationship between you and the strongest male influence in your life. How was that relationship? Now consider what messaging you received from that relationship (or lack there of) and the affects it might have on your romantic relationships today. Was it a close relationship, was it distant, abusive, was there a relationship? It  matters. Ask yourself, what am I really afraid of?

     If You “like” Chef…yes, i said “like”(you can love someone, but not like them) I mean really like him, want to be around him, like his company and can see yourself liking him for a long time, and he likes you the same, then know that this is what long-lasting love and long term relationships are made of.  You can get the as same amount of information without living with him. You just have to keep your eyes open.

    Make sure you’re not repeating patterns of sabotage by understanding why you love the way you do, why you love who you do, and make a move based not on fear, or what we suggest, but because you want to, no matter the outcome.

    • June 13, 2012 9:21 pm

      Wow, what a beautiful comment. There is so much I want to say, to write, but I’m not in a place in my life where I feel comfortable to discuss some things. But your thoughts on other figures in your life is very poignant and has definitely given me something to think about. And the part of your comment about liking someone… wow. Here’s the thing, I really like spending with Chef. We have so much fun, and I really look forward to seeing him almost every single time. I feel realy lucky to have that. Sometimes you forget that not everyone has that. Thanks for reminding me.

  7. June 7, 2012 12:35 pm

    First, it’s great you’re asking yourself (and your readers, ahem) this important question. The 28 yr old you met with the new born is probably exhausted and with 4 kids under her belt, has probably missed out on her youth. There is a price to pay for starting so young. Although you may not feel like it, you have lots of time for babies. Your bio clock is in prime mode and will be for many more years to come. If I have to weigh in, I say don’t put a deadline on this decision. A deadline = dead. I just don’t like that idea. If he has to move, don’t make that the reason to co-habit. He sounds like an amazing man and so he will be patient and there is no pressure to ‘decide’. Don’t ante up the stakes with a deadline. Best to you!

    • June 13, 2012 9:16 pm

      “Dont ante up the stakes with a deadline.” Wow, your comment really had a calming effect on me. It’s like you gave me some permission to take my time. I don’t know what’s going to happen next week or month, but you made me feel a little better for this moment. Thank you!

  8. June 7, 2012 1:37 pm

    I think dating is nearly always high stakes … after all you can lose your heart and have it broken or change your life forever

  9. June 7, 2012 2:15 pm

    Hi there! I agree with Lisat that it might be a bad idea to put a deadline on your decision. I respect that you want to push yourself to make a decision, but diarizing it might cause more stress than good. Good for you for taking time to think all of this over, but at some point, (as Mikalee wrote), you have to trust the voice inside. However faintly it is speaking.

    P.S. I’m back in RVA from London now if you ever want to catch a drink/coffee!

    • June 13, 2012 9:11 pm

      ATA, I’m just now seeing your comment! Yes! I would love to get together! Email me at so we can figure out details.
      Thanks for the advice on this – technically, there needs to be a deadline on when we decide whether to live with eachother right now, because we have to sign leases and such. But it doesn’t have to be a deadline on whether we live together EVER. I’m listening for the voice. I’ll let you know what I hear 🙂

  10. June 7, 2012 7:51 pm

    I see where you’re coming from, but don’t necessarily think that dating is high stakes yet at the ripe old age of 27. Many women are pushing having kids back to their mid and late 30s nowadays. Better to be absolutely, positively (as much as one can be) sure about a possible future with somebody first. Don’t think of that year as “wasted” if things don’t work out – consider it a valuable investment in determining whether or not that person is truly right for you.

    Obviously my answer is “move in together” even though you aren’t actually polling your audience!

    • June 13, 2012 9:34 pm

      Haha, thanks Mark, for your non-official answer :). I so admire you and the relationship you have. Sometimes I get a little jealous because you seem so sure with your lady. There are two options: 1) You and the lady are truly meant to be and it’s so obvious to both of you or 2) You have a way better attitude than me and are able to live your life with no regrets. Either way, I’m sorta jealous. 🙂

  11. June 7, 2012 8:24 pm

    I’m with Mark, it’s not high stakes. The bottom line is although you wish, hope, want, desire it to be forever…it doesn’t have to be. Obviously you love him. You list off all the right reasons. So what is holding you back? THE EX. And he isn’t even in the picture. It’s feelings that are holding you back. Time to let those go. Take a deep breath, go on a vacation BY YOUR SELF and think about it if you must. Don’t base a life decision on something SOMEONE else did to you. It’s not fair to Chef. If you aren’t ready, then the answer is – you don’t want your forever to be with Chef.

    • June 13, 2012 9:09 pm

      That you Edmonton Tourist – appreciate your advice. It seems pretty sound 🙂 Lately, I’ve thought that I’m completely over the ex situation, but moments like these I am doubtinf myself. Maybe there is still some of that pain left. But you are right, that’s not fair to Chef at all. Thanks for commenting.

  12. Nikki permalink
    June 8, 2012 10:59 am

    YAY! Your posts about you are my favorite! Sleepovers are the testdrive for living together, living together is the testdrive for marriage. Be your own life coach and listen to your gut- is it ever wrong?? I actually married the guy who shook my trust to the core so I know all about that. We’ve been together for 17 years, have 3 great kids and are still very happy – sometimes you just have to go for it. :o)

    • June 13, 2012 9:07 pm

      Thank you so much 🙂 I love that you agree with test drives, lol! Your marriage sounds amazing, I need to hear more of these stories – I feel like all I hear is horror stories of relationships gone terribly wrong. I appreciate your reading and commenting!

  13. abertawycopr permalink
    June 8, 2012 3:04 pm

    Let me throw a spanner in here..if you don’t get married, then eventually, and better sooner than later, you’re going to have to split up, unless you both make a very similar commitment to marriage, and save bigger decision for when the kids come..

    • June 13, 2012 9:03 pm

      Fair point abertawycopr, I definitely couldn’t put off this decision forever. But I always just thought that Future Catherine would handle these kinds of decisions and I could chill out for now 🙂

  14. June 10, 2012 10:00 am

    I’m probably not the best person to ask..if your ultimate goal is to legally marry AND if having children is important to you.

    I’m neither– meaning I’ve been with my partner for the last 20 years and not married. Neither of us need a piece of paper to say “we’re married” nor do either of us need a wedding ring to seal the deal.

    And I chose to be child-free… In my mid-20’s onward, I did not want to have children. I have not regretted this but then that is a whole other topic. (I am the eldest of 6 children. Youngest is 10 yrs. younger than I. Yes, a good part of teens was looking after my siblings.)

    He did have a divorce with his ex where it landed in court and they had joint custody of their children. They are now adult and have been living independently for last 12-16 years depending which “child”. The eldest is…..33 yrs. old

    I really feel “living together” as an expectation for ANY couple under just 1 home is a bit of a red herring, since no couple should feel compelled to live together in the first few years.

    We met when I was 31 yrs. ..just a few months after I bought my own condo. By then, I gave up finding “Mr. Right”. He was recovering from a recent divorce. Also his children were 11 & 13 yrs.

    Seriously, I had no interest to deal with children who were “mourning” for their parents’ divorce and who would always have allegiance to their birth mother. So for me, I was not interested in sharing a home with this type of family situation. It was just wrong time for everyone.

    And I wanted to enjoy my own home. I continued to pay my own mortgage I planned all along.

    So for the next 14 yrs., he and I spent time at each other’s homes. (He had his own place…16kms. away) We cycled to each other’s homes, etc. I occasionally spent time with the children. I was not their mother nor did I pretend to be. He and I were in contact daily….either in person, phone or Internet.

    Meanwhile there were nieces and nephews popping up in my own extended family, so I never felt children didn’t contribute to my life.

    In hindsight, it was the best thing we did for HIS children as well as foster peace amongst us all: that I wasn’t directly involved (nor had interest) in raising them as a step-parent and for everyone, it minimized angst, conflict for a situation that already for teen years, for any teen, it’s tough enough.

    Then after surviving a long distance relationship with him when he was mandated by his employer to move and live 1,000 km. away, I left my job and moved 3,000 km. west to live with him in 1 home for next 8 yrs. It was great.

    Life has gotten complicated since I accepted a job in another province after job hunting for 18 months. So now, we are splitting time across 2 homes in 2 provinces. But for us, this is no-brainer: we’ve done this before. Communication every day is important to us and we look forward to sharing with each other what we do, what we think.

    I have lost a sister and will lose my father (to prostate cancer) in few years.

    Meanwhile dearie has a 2nd grandson soon to arrive. I am 53 and he is…69. We have been together through a great deal …and believe me, HE is the one for me…for life. And for him, he has shown every action of his, that I am the one in his life.

    Marriage is not the ring. It is the trust, faithfulness, respect , patience and joyful ability to learn together. If something should fall apart with him…but more, if he is no longer alive..I know my life has been made better and infinitely more interesting.

    If children is part of your future game plan, yes I can see the interest in figuring out marriage or living together. But if children are not part of your game plan (I am referring to readers here), then what IS the big rush?

    LOL, I really have flouted every rule about the wedding ring here.

    (Gee, I should have written maybe a guest blog post?)

    • June 13, 2012 9:02 pm

      Wow Jean,
      Thank you so much for sharing your story and background. If I didn’t know from your past comments, you are definitely a different kind of woman. I really admire your strength and experiences. One of the things I wondered from your story – when you and your partner moved in for the first time, after 14 years of living apart and being together, were you scared about the change? You must have become pretty used to your space. Did it worry you?

      Your suspician about me is correct – I definitely want to get married and have children. I’m just on the beginning stages of worry about my age in that realm, so that’s probably a good thing. That’s to say the situation is not dire or anything :). I really appreciate your story and advice.

      By the way, if you ever DO want to write a guest post, I would welcome you!

      • June 16, 2012 6:53 pm

        We were living apart but living in the same city so lots of times we spent a few days at each other’s place. So moving together under 1 roof was not a big deal.

        The bigger deal was leaving my job and moving to a totally different province. Then I had to find a job there.. But no, I didn’t regret the decision.

        He is a naturally neat person. I am not. Fortunately he is more tolerant than I am. But for me, having my own home first, woke me up the reality of looking after a home and cleaning up.

        I’m sure things will fall into place over time, Catherine. My best wishes for the journey ahead.

        I’m not sure I have anything left to even write a guest blog post. Too much yapping here.

  15. Charlotte permalink
    June 11, 2012 3:02 am

    Catherine, you should be honest to yourself. It´s been more than two years since the Big Bad Breakup. Chef looks like a great guy and also good husband/father material and based on what I read about him, he´s just perfect, but it seems to me you are not in love with him enough to be his wife. If you loved him, you wouldn´t doubt everything so much. You would jump into air with joy. If your heart doubts the marriage forever ever after idea, it´s not meant to be. Trust your heart, you are still very young and you don´ t have to settle and base your decision on the reason and age. You deserve to have your fairytale , don´t lie to yourself if you don´ t feel it. Because you wouldn´t just hurt yourself, you would hurt him.

    • June 13, 2012 8:55 pm

      Hi Charlotte,
      Thanks for taking the time to comment. I believe you’ve expressed similar thoughts in the comments before, and I appreciate your perspective. However, I just don’t think anyone knows what’s in my heart besides me. And I don’t do our relationship that much justice on the blog. I write about my worries, or my insecurities – I don’t write about the amazing times we have nearly as much. It’s really not fair. Part of me really wonders if my hesitation is really me just trying not to get hurt. But I’m not ready to jump to conclusions and I am definitely trying to follow my heart. Thanks for your advice 🙂

  16. June 11, 2012 1:59 pm

    Try not to worry. You’ll figure it out. You’ll feel it.

  17. June 13, 2012 7:41 am

    I just reread towards the end of the original blog post: a deadline for approx. end of July to be with or not with chef???

    Life doesn’t always work on a deadline like that especially for family and dear friends. Other things happen to each partner along the way also. Deadlines work if you expect a person to pay you back a loan, return a loaned item.

    • June 13, 2012 8:47 pm

      Hi Jean,
      NO – false alarm! Just a deadline of July to decide whether to move in with each other right now. I wouldn’t put a deadline like that to decide a whole relationship. It’s just whether we’re ready to move forward.

  18. annie permalink
    June 15, 2012 1:36 am

    Your statement “part of me wonders if my hesitation is just me trying to not get hurt” is probably very accurate. I know for myself being independent and self sufficient is my way of avoiding getting hurt (although it actually ironically does the opposite.) I think at some point you first have to decide that you are going to allow yourself to be vulnerable and take a great (but calculated) risk. Then, you have to decide is Chef the one you want to risk that with (I vote yes!). I’m guessing you are also questioning your own judgment and need to somehow find the way to believe in yourself and your assessments of Chef.

    I do not believe you have to live with him before you are married, you said you learned about your ex’s badness after you moved in, but I bet if you looked back on your relationship you knew he was bad news before you moved in, you just didn’t trust your judgment and overlooked the signs or made excuses (like I did).

    You will make the right decision, I’m sure! Here’s another tip to help : imagine you just got bad news today (as in I need brain surgery news), who would you want to go thru that with you?? That’s the question I am asking today, and its not the person with me, its the person I lost because I was too tough and independent and couldn’t get over my fear and anxieties and truly commit to him.
    Good luck Catherine, you will make the right decision whatever it is.


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