Self-Love After 50: 6 Hidden Obstacles That Block Love
If you’re thinking about dating again after a long time — or maybe you’re wondering whether you even want to try — I want to start by saying this: there is no expiration date on love.
You are not too late.
Your history is not preventing it.
What you've been through is not preventing it
What I see again and again, after decades of working with women in midlife, is that the biggest obstacles to love aren’t usually the ones we complain about out loud. They’re not the apps. They’re not the men. And they’re not the culture.
They’re the quiet, internal stories we’re carrying — the ones that shape how we show up before we ever sit across from someone at a table.
Self-love is foundational. If you don’t feel at home with yourself, it’s incredibly hard to imagine someone else loving you well — and even harder to let it in when they try.
Today, I want to walk you through six hidden areas that quietly undermine confidence and block love, especially for women over 50 who have lived full, complicated lives. These are not flaws. They’re unfinished business — and the moment you bring them into the light, they become treatable.
1) Body Image
If you are one of those women who looks in the mirror and criticizes what you see—your face, neck, arms, breasts, hips, thighs, tummy, tush, or veins, your wrinkles, your age spots, or your rolls (oh, the list goes on!)—you are not alone.
But you do have a poignant choice to make.
You can keep beating yourself up, blaming age, metabolism, social media, and Western culture for your insecurities. You can stay in the cycle of shame eating, overanalyzing your body size, and comparing yourself to younger women. Or: You can accept your body exactly as it is.
This one takes real courage. It means asserting that your physical appearance is not a problem to be solved.
The right person—the right match—will love you exactly as you are.
There are men who love rolls, don’t even notice cellulite, and think wrinkles are sexy.
Self-love and acceptance are magnetic and attractive.
Reminder: Men aren’t nearly as critical as you are of yourself.
Or you can change what you can and accept what you can't.
This one is the hardest—and the most balanced. It starts by acknowledging that, yes, your body changes over time. Fat distribution shifts. Hormonal changes and menopause alter your body in countless ways.
But you can influence your physical fitness, your well-being, and your attitude toward yourself. Small consistent actions—a daily walk, strength training, how you eat and drink—boost body confidence and vitality faster than any “quick fix.”
This was the choice I made. It started by changing my relationship to sugar, because it was doing the most damage to my body, moods, and self-esteem. As soon as I cut sugar, I felt better, rested better, slimmed down, and started to feel sexy again.
You, too, can feel sexually attractive, powerful, and desirable again.
2) Bad habits: the quiet drain on self-confidence
Drinking. Nightly pot. Overeating. Spending. Gambling. Screen time. Overworking. Whatever yours is.
There’s a range here. Sometimes it’s a little bit annoying and makes your own life more complicated. And sometimes it’s a serious problem that has taken over — and if you feel powerless, I want you to treat that as a mental health issue and get real support (therapy, groups, 12-step, the most rigorous help you can access).
But if it’s not addiction-level — if it’s a habit you can change — I want you to understand why it matters for dating:
Because anything that erodes your integrity erodes your sense of self. And when this happens, your self-esteem issues show up on dates even if you never speak them out loud.
This is the moment where you stop pretending it doesn’t matter. Admit it to yourself. And if you’re brave, name it (even privately). Confident people aren’t the ones who never struggle — they’re the ones who face their patterns and take the first step. Most people with high self-esteem also worked to earn it and had help from supportive people. Don't go it alone.
3) Flirting and sex: you’re not “bad at it,” you’re rusty
So many older adults tell me: “I’m just not good at flirting,” or “I don’t know how to be sexy anymore,” or “I feel awkward.”
First: that’s normal.
Second: it’s not a permanent identity. It’s a skill.
We act like flirting is something you’re born with, like it’s eye color. Wrong. Flirting is a learnable skill. Being "good in bed" is learnable. You can practice playfulness and communication--the two most important factors.
And yes — practice is a great way to build real confidence. Not only thought-based confidence. Body confidence. The kind you feel in your bones.
So if you’ve been hiding in your comfort zone because you feel rusty, I want you to do two things:
✅ Learn (books, videos, resources).
✅ Practice (in tiny, low-stakes ways with new people, in conversation, even if it's the person checking you out at the grocery store.
At the end of the day, you’re not trying to become a universal flirt or be “good in bed" in general. Rather, you need to learn to be present with a specific person — and learn what they like. So everyone really is a beginner in a new relationship, but having put in hours of practice beforehand translates to being more sure that you can create attraction and intimacy.
4) Family relationships: the sabotage you don’t see coming
This one surprises people, but it shouldn’t.
Your family ecosystem has a balance. And when you start moving toward new relationships — that balance shifts.
Adult children may feel competitive for your attention, worried about inheritance, or quietly threatened by the idea that you’ll prioritize a romantic partner again. Aging parents may need more from you than ever. And you can get pulled into guilt without even realizing it.
Here’s what I tell my clients: you have to fortify these relationships so they’re sturdy and flexible.
Because if you don’t, you’ll sabotage your love life “for them,” while telling yourself you’re just being responsible.
So your next step is this: get clear on how you want to relate to your kids and your parents going forward. Then have direct conversations —to get to the bottom of what everyone needs (including you).
5) Previous relationships: if an old chapter is still open, love can’t move in
Ideally, your exes are closed chapters — you learned, you grew, you moved on.
But if you’re still mentally revisiting a past relationship, replaying arguments, carrying resentment, or even thinking "the one got away," your subconscious is still living there.
And when the past is taking up space, it quietly lowers self-esteem. It tells you a story about what you deserve, what always happens, and what love “means.” That story becomes a self-fulfilling prophecy.
If your last time trying to date ended in heartbreak and you never processed it, I want you to stop calling that “just life” and treat it like the unfinished business it is.
Sometimes the work is practical — clearing out reminders.
Sometimes it’s emotional — extracting the lesson, releasing the fantasy, letting go of the ache.
Sometimes it’s relational — making amends, asking for an apology, or accepting that you won’t get one.
And sometimes? You need support. Real support. Because this isn’t a quick fix. You can email me about coaching.
6) Unresolved hauntings: the old pain that still runs your dating life
This is the deepest one.
Unresolved hauntings are the things that happened a long time ago — but still live in your nervous system. Childhood pain. Past mistakes. Rejection that hardened into a belief. A moment that created a negative theory about yourself, romantic relationships, or people in general.
And if you’ve ever felt your body go into panic on a date — like dread, shutdown, or spiraling — that can be your system reacting to an old wound. (If you’re dealing with panic attacks or suicidal thoughts, please treat that as urgent and get professional help right away. You are worth protecting.)
Here’s the first step — the only step I’m asking for today:
Write it down.
Get the subconscious conscious. Name what’s haunting you. Because when you can name it, you can change it. Then choose a path: therapy, coaching, or a support group. Start talking about it in a safe space.
If it’s big enough to block a good relationship, it’s big enough to deserve attention.
The reset that actually works: promises, not resolutions
Now let’s bring this into the real world — because it’s New Year energy, and I don’t want you making vague resolutions that fizzle out.
Resolutions are fluffy. Promises are concrete.
A resolution says: “I’ll try.”
A promise says: “Here is exactly what I will do.”
Examples:
✅ “I’ll eat healthier” becomes: “I’ll have dessert twice a week, one serving, and that’s it.”
✅ “I’ll heal” becomes: “I’ll contact three therapists by January 10 and book my first session by January 16.”
✅ “I’ll date again” becomes: “Starting January 2, I’ll spend 30 minutes a day building my profile until it’s live.”
And here’s the secret weapon: add a consequence.
Not self-punishment. An annoying, immediate consequence that keeps excuses from running your life.
Miss your daily dating-profile time? You clutter-clear one space.
Break your dessert promise? No dessert next week.
This isn’t about being harsh. It’s about building trust with yourself — which is how self-esteem is built, not with positive affirmations alone, but with follow-through.
📺 Watch the full podcast episode here
If you’d like to watch the episode I made about self-love on my podcast Love at Any Age, press play on the video below.
Coaching homework: pick ONE obstacle and take the first step
If you do nothing else after reading this, do this:
✅ Pick one obstacle that hits home (body image, bad habits, flirting/sex confidence, family dynamics, exes, or unresolved hauntings)
✅ Write down the “truth zero fluff” version of what’s going on.
✅ Choose your first step and put it on your calendar.
The end goal isn’t being perfect. It’s becoming more of your authentic self — the version of you who can receive love, because you know you deserve it.
And yes, Dating Sunday is coming. But more importantly, your life is happening now.
Frequently Asked Questions about self-love obstacles in dating after 50
1) Can low self-esteem really affect dating if I act confident?
Yes. You can “perform” confidence and still make choices from a lack of confidence underneath. Low self-esteem often shows up as over-giving, tolerating poor behavior, picking unavailable partners, or dismissing your own unique qualities to keep someone around.
2) What if my negative self-talk feels automatic?
That’s common, especially if it’s been there a long time. The first step is noticing it without treating it like “truth.” Write down the phrases you say to yourself on a regular basis, then challenge them with evidence from your real-life experience.
3) How do I stop old past relationships from affecting new relationships?
You don’t stop it by “trying harder.” You stop it by resolving what’s unresolved: extracting the lesson, releasing the fantasy, grieving what didn’t happen, and rebuilding your sense of self so you don’t date from old pain.
4) Is it normal to feel rusty with flirting and sex after divorce or widowhood?
Completely normal. It doesn’t mean something is wrong with you. It means you’re human. Treat it like learning new things: educate yourself, practice in small ways, and focus on presence rather than performance.
5) What if my family is against me dating?
Then you need clarity and boundaries. Family members may be anxious, protective, or self-interested. Your job is to treat those relationships with care — without handing them the steering wheel of your love life. Clear conversations now prevent sabotage later.
Love,
