Never Give Up More than You’re Willing to Lose

Never Give Up More than You’re Willing to Lose

I live on the ocean and I’ve grown up spending a lot of time at the ocean, whether it was the cold waters and shell covered beaches of Massachusetts or the warmer waters and sandy beaches of Florida or the quiet beaches in the Carolinas there is one thing in common and it’s that building a house on the water is expensive and if you aren’t dripping in money, are not a great investment financially.  Between the slowly encroaching pitfalls of beach erosion and the fast acting hurricanes that can flood or tear down your house overnight, getting home-owners insurance is expensive and in some cases, impossible.

Many years ago I was considering a move to Austin Texas and went for a trip down to Galveston, TX with a friend. I met with a real estate agent who took me around for the afternoon showing me enormous McMansions in heavily manicured suburban neighborhoods.  Housing prices were inexpensive at that time (not sure what they are now) and as I was moving from California where money didn’t go as far, I was fascinated.  After looking at the suburban homes, she took me to look at some of the homes on the water, not to persuade me to buy one, merely to show me the waterfront and the available real estate there. The homes varied in scale and design from very modest to more ornate.  There was such a wide variety I asked her what made it that way and she told me that due to the frequent Hurricanes, no one on the ocean or the inlet could get flood insurance.  “You only build what you can afford to lose.”  Meaning, if you want to live there, build enough of a house to enjoy it with full knowledge that if it is destroyed in a storm, it will be your money needed to rebuild.  No bank will bail you out.

So much in life is a gamble. While you can do your best to stack the odds in your benefit, there are simply no guarantees.  Natural disaster, human error, misinformation.  Even with the best preparation and intentions, things don’t always go as planned.

In dating, especially modern dating where we go on a series of blind dates via online dating or introductions by friends of friends,  so often we are moved to go “All In” on a hunch. We get caught up in the excitement of connecting with someone. We have a great history of communicating online, then have a great first date. He appears to be “so different” and we are swept off our feet, right into bed!

It is exhilarating to get caught up in the moment. To believe in the fantasy. But that’s all it is at that point: a fantasy that likely we have written in our own minds, to our own detriment.

In the days after, when he doesn’t call, we sink. We battle with ourselves, wondering if we said something wrong. Doubt is overwhelming and consuming.

I get it! On the one hand, we are grown women and we enjoy sex and we are thrilled to feel a connection. Especially if we have gone so long without one. Or if our daily lives are filled with responsibilities and stress we are practically tripping over ourselves to be “swept off our feet.”

Sex isn’t as intimidating or overwhelming as it once was.  We’ve been married. We’ve been in long relationships. We’ve had a lot of sex. We could have sex in our sleep! Ok that’s sad. Ha! And we are comfortable with our bodies. We’ve lived in them long enough we’ve found ways to love them, or love them enough, to be satisfied. We’re less inhibited. We’ve birthed babies, we’ve been naked in front of men who were delighted with our naked bodies and have no reason to believe the next man won’t be just as thrilled to explore us inside and out.

While it’s true we’ve earned a freedom with our bodies and we live in an environment that doesn’t judge this sexual liberation, the truth is, for most of us, we don’t have that same liberation with our hearts. And our hearts are solidly nestled inside our bodies.

Somewhere along the line we’ve confused the idea that it is our choice to share our bodies however and with whomever we want and that to prove our liberated, empowered sexual enlightenment we should back this up by freely giving it.

Yes, we want love. Yes, we want sex. Yes, it is our choice where and how we find and give it. But too often, we give away more that we are willing to lose.  The storms come more often, taking a bit of siding off our beautiful oceanfront home here, tearing up a bit of the roof there, perhaps the wall is torn out by an unexpected, painful breakup storm.

We are doing more rebuilding than living. We are riding the highs of the initial chemistry, the first dates, the attention and we are going all in on a whim without ensuring we have built on a solid foundation, with strong sides.

Now, I’m not saying not to build. Too often, after a few setbacks we retreat into defensiveness. We get set in anger and decide that it is the world that is unfair. “Men are awful.” That’s not helping anything.  Men are often just as confused as we are. This isn’t just a brand new world of dating for them. Sure, some aren’t truly interested, but a savvy dater can read these signs fairly quickly.  Others are ready to invest but wonder why the house is being offered so eagerly.

This is where I’ve likely made you uncomfortable. You are ready to argue with me that you are just fine and you can do with your body what you want! I’m not disagreeing with that and I’m not shaming or judging you. What I’m trying to say is that if we pay attention to how we feel after a disappointment, after we’ve gotten caught up in our emotions and our dream building and when we come crashing down with the knowledge that Prince Charming was yet another toad then we are forced to admit that it’s NOT as easy as it seems! If we weren’t investing more than we were willing to lose then we would literally have no regrets! We would walk away untouched, unaffected.  This may be true for some of you but for many of you, I know it’s not true. It wasn’t true for me. I wanted it to be true! Wouldn’t it be great to have no consequences! To be a free spirit giving with no need for anything in return? To be unfucking touchable? But do we even want that? When we take a step back do we really want to be unaffected, disconnected, impenetrable? Hell no! We want to love big, winner take all! We want to live brightly with meaning, with intention!  We can’t have it both ways. We need to choose. Will we keep our walls up? Will we be reckless? Or will we do the work to find that happy medium and stay the course?

Alas, I’m a human woman! I’ve got big tits and big ambitions. I’ve got a big appetite for bad decisions.   I take chances, steal kisses, give too much and pay the consequences. I am powerful and fragile. I love too much and too fast and without restraint. But I also learn.

I was giving up more than I was able to lose. And so I changed.

I don’t mean to overstate the comparison with home buying as if relationships are an exchange. I don’t want to do that. I’m simply trying to express that we need to be savvy. The truth is always revealed in time. But too often we do not take the time to find out our date’s intentions. We find out two months in that he’s still hung up on his ex, that he’s not been able to keep a steady job, that he’s got a drinking problem or an anger problem.  But instead of being able to walk away with dignity and self-respect we are tangled in the drama because we have invested ourselves emotionally and sexually in this person we did not really know.

When you remember not to invest more than you are willing to lose you can easily remind yourself of the non-negotiables:

  • Your dignity
  • Your health
  • Your emotional well-being
  • Your self-esteem
  • Your responsibilities
  • Your family

If any of these would be put at risk by investing emotionally in a relationship with someone, you know to walk away.  We cannot possibly know how involvement with another person will affect us after a couple dates. And once we are emotionally invested or sexually attracted, we are all fools for love. Our judgement is compromised. This is why it’s important to show some emotional and sexual discipline to not go “all in” before we’ve found out more about this investment.

Everyone we become intimately involved with is an investment. We are givers, we are lovers, we attach and if we attach ourselves to someone harmful, we will be affected by it. He will be another storm.

We’ve had enough storms, haven’t we?

Never Invest More than You're Willing to Lose - Kitten Holiday
Never Invest More than You’re Willing to Lose – Kitten Holiday

The riskiest part of this is, most of us, coming out of divorce or the end of a long relationship, or a series of failed relationships, have already given too much already. We are tired, we are fragile and broken in places that we haven’t fully repaired. We know the bliss of building but we aren’t completely ready because we are investing from a deficit.  We are in emotional debt.

While you are the only one who can know where your limits are, what your risk tolerance is, how much you have to offer and how much you are willing to lose, I intend to help you in this blog to either better define this for yourself or better hold yourself accountable or both.  We’ve been fed a lot of lies about what it means to be a woman, what it means to be strong, what men want and what we want.  We have to open our eyes to the truth about ourselves, the people we are dating, our own hang-ups and delusions and the world we live in so that we can truly create the lives we want.

I will write about this in another post but this is part of my passion behind Kitten Holiday and No Bullsh!t dating advice. I will help you identify when you are being swindled into a bad deal, or building a castle in the air so that when you are ready to build you can be confident in your investment that you will even let yourself splurge on the frills.  Getting to this place means we need to get out of emotional debt and build up to a place of abundance.  When we are in a place of emotional abundance we do not seek outside validation. We do not need to build on loans. We are confident in our investment and trust our decisions. We have gratitude and faith.  Getting to this place is both easier and harder than it sounds. It requires going through a shift in mindset where we abandon the fantasy and take stock of reality.  This can be hard because reality can be stark, but it is where we have to begin.  Once we make the journey, it’s absolutely worth it.

If you’d like to read more about getting out of emotional debt and developing a mindset that can bring you to a place of abundance and gratitude that will set you up for success in all areas of your life, please subscribe to my blog in the top right hand corner and sign up for my newsletter.

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18 thoughts on “Never Give Up More than You’re Willing to Lose”

  • Such sound advice. In the past, I have made the mistake of investing too much in the wrong relationships and giving up my dignity and hurting myself in the process. Thankfully, I wised up.

  • Great reasoning and sound advice – from the perspective of someone that isn’t in the dating scene. Hindsight provides such clarity, but I’m sure I would not have been able to value the wisdom of your words when I needed it. Thanks for sharing – love your insight!

    • Thank you for reading! And yes, I do feel like I write to those who are already converted. We all learn the hard way, don’t we? However if those of us start to talk openly about theses things maybe it helps to articulate the path to healing for someone in the midst of their lesson? Always hoping!

    • Thank you for reading! And yes, I do feel like I write to those who are already converted. We all learn the hard way, don’t we? However if those of us start to talk openly about theses things maybe it helps to articulate the path to healing for someone in the midst of their lesson? Always hoping!

  • Great reasoning and sound advice – from the perspective of someone that isn’t in the dating scene. Hindsight provides such clarity, but I’m sure I would not have been able to value the wisdom of your words when I needed it. Thanks for sharing – love your insight!

  • I enjoy your writing. It is refreshing to hear from women who try to understand the human perspective as opposed to framing things as men vs women.

  • I need to say amen sister. So well put that after a divorce or a long relationship we are in emotional debt. I’m there with you! Love your fresh perspective!

  • One of, if not the, favorite posts from you. The metaphor of real estate is truly one that matches well with dating and the internal negotiation of how far to take the next step and how much to invest and when to invest. Good stuff Kitten

  • I believe it comes down to a life worth living means to invest in a life worth dying for. I don’t think there’s anything more powerful than family & if your not willing to die for family or your freedom, then how could you ever build a family of your own? What about those who fight for family, community or country? We all want the same thing & if fear stops us from this will, want or need, then those you love could never be safe, no? How could you ever invite another into a storm, on the same note, if we are a work in progress, would fear stop you from a life you want? Dreams are what this world needs, it’s built upon them, yet, hearts are torn & broken as we try to just live. If we wait till we are perfect, then we will wait till we are in the next life to live in love or at least try to…no?

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