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November 28, 2023 By Cosmo

Unlucky in Love? Smart Dating Tips to Master Your Dating Life Before You Fail Again

Unlucky in Love - Smart Dating Tips to Master Your Dating Life

Fans of the classic TV sitcom Frasier will remember the main character’s relentless streak of bad luck with relationships. You can certainly say he was unlucky in love.

From the moment he gets a date with a woman, his sub-conscious works to sabotage it, much to his consternation and our amusement.

Although he dated dozens of women over the 11 seasons the show ran, Frasier never seems to get it right. Or, the few times he does find the right woman, he blows it somehow.

His problem is one he never comes to grips with — himself.

Of course, his dating mishaps and mistakes are fodder for comedy and drama. But if your dating life is like Frasier’s, you know there’s not much to laugh about. And if there’s any drama involved, that’s no help either.

Why Am I Unlucky in Love?

But is there really such a thing as being unlucky in love? Frasier’s tales of dating woe are all too real. That’s probably why it was such a hit for so many years.

He has an astounding arsenal of tools to prevent a mature relationship from ever developing. The reality is that his unlucky streak in love is completely self-inflicted.

  • He constantly lies to make himself seem a better catch than he really is. Of course, when he’s found out, the relationship ends.
  • He picks women who are exciting at first but eventually exhibit their mean streak. The inevitable arguments lead to a breakup.
  • He has impossibly high standards for his women. When unavoidable disappointment sets in, he ends the relationship.
  • If things start to calm down, he gets bored and succumbs to fear of missing out. “What if there’s someone better out there who’s not so boring?”

In short, the women he dates never stand a chance. He’s put up enough obstacles that he’ll never have an emotionally healthy relationship. That’s the way he wants it.

Despite his well-groomed appearances and fussy, narcissistic manners, he’s not the kind of man a healthy mature woman would want to introduce to her family!

If, like Frasier, you have good luck getting dates but bad luck with relationships, it’s time to pick up a mirror.

There’s an axiom in recovery programs that says, “whenever I am disturbed, there is something wrong with me.” Your streak of bad luck with relationships has less to do with the women you date and everything to do with you.

It’s time to get to know yourself better.

4 Ways to Tell If You Are Unlucky in Love

Here are four easy ways to tell if you’re to blame for your bad luck with dating. I also offer several tips on how to take control of your dating life once and for all.

1 – Facing a lot of rejection on your first dates?

facing rejection on first dates

Maybe you expect to pick up a princess but you’re not exactly a Prince Charming.

Matchmaker Lauren Pena writes in The Truth: 5 Real Reasons You Have A Hard Time Finding Love, that this is one of the common reasons people strike out — they’re shooting out of their league.

Perhaps you expect to attract women with a fitness instructor body but you haven’t exercised in twenty years. It’s not going to happen.

It might be hard to hear, but Pena also mentions four more reasons you appear to be unlucky in love.

  • You have a fixable physical issue that you’re not dealing with. (Disheveled hair, bad teeth, body odor.)
  • You’re not interesting. No hobbies or interests except work.
  • You have a mean or sarcastic sense of humor better suited to junior high than the golden years.
  • Your finances are a mess.

As mature men, we’ve spent a lifetime acquiring habits good and bad. If you can admit you’ve let your self-care habits slide, you can get started on fixing them.

If your habits include an addiction of any kind, you’ll need to deal with your addiction before you can have a truly fulfilling relationship.

Bad habits can be broken and replaced with good habits. You have to decide that you want to make the change, then take an action to head in that direction.

2 – Do you choose the wrong kind of women?

do you date the wrong women

Picking the wrong people was a life-long pattern for me. Aside from dating and marriage, I also tended to pick less-than-ideal people to befriend personally and work with in business.

There was plenty of excitement in my life, and a lot of drama, but never the satisfaction and true peace for which I was searching.

Then I returned to therapy. With a little work, I managed to root out the sub-conscious motivations that caused me to repeatedly fail at romantic and personal relationships. I needed that outside, independent viewpoint to hold the mirror up to my personality and it was well worth the effort.

Today, with my partner Daisy, I’m in the best relationship I’ve ever experienced.

It wasn’t a matter of luck. It was a matter of choice. Just as I did, you can decide to take control of your dating life once and for all. If counseling is needed, so be it.

It’s also possible the reason you end up with the wrong kind of women is simpler.

You haven’t defined who you really want. If so, take time to figure out who your ideal partner is for a good relationship. Take time off from dating and spend a weekend figuring out what kind of person would truly suit you as a partner.

3 – Are you lying to yourself about the kind of relationship you want?

Frasier could never just be himself. He had to appear to be the person he thought others would want him to be, no matter the cost. Of course, the mask always falls off. His dates always found out what he was really like.

For instance, are you trying to be a serial dater, going out with many women because your friends think it’s the cool thing to do, or you think that’s how it’s supposed to work?

Well, if it goes against who you really are, it will never work. Yes, you’ll get dates, but you’ll never get a good relationship. Then you’ll blame your “bad luck.”

Learn to be authentic. If you’ve spent your life changing your behavior to make others happy, you’re stuck in what psychologists call co-dependency.

When you relax and be who you’re supposed to be, you’ll attract the right kind of woman for you.

4 – Do you feel sorry for yourself and your woes with women?

feeling sorry for yourself and woes with women

When you feel sorry for yourself, you’re playing the victim.

The fact is that you, and you alone, are in control of your life. If you’re angry about where you are in life, you might play the victim to shift the blame from yourself to others.

When you play the victim, you attract caretakers and rescuers. In time, they’ll tire of the demands placed on them to care for you. When the relationship sours or ends, you’ll bemoan, once again, your streak of bad luck in love.

Playing the victim is a choice. As with other life-long habits, it might require some outside help to get a healthy outlook on life.

Conclusion – How to Be Lucky in Love Starting Right Now

Look at the relationship patterns in your life, including friends and work. Are you too much like Frasier?

Repeat patterns of relationship failure are a clear signal that something is amiss.

  • Not happy with your dating history? Talk to a therapist.
  • Getting plenty of dates but lots of rejections? Take a look at how you care for yourself emotionally and physically.
  • Feeling sorry for yourself a lot? That’s a signal for a change in your mindset and behavior.

Author Iyanla Vanzant says,

“Everything that happens to you is a reflection of what you believe about yourself. We cannot outperform our level of self-esteem. We cannot draw to ourselves more than we think we are worth.”

Get to know yourself even better than you do now. You might be surprised at the incredible person you find locked away inside.

FAQs on Smart Dating When You’re Unlucky in Love

What’s going on?

Why do I seem to be unlucky in love?


The perception of being unlucky in love often stems from recurring relationship issues. It might not be about luck but about patterns and choices. For instance, impossibly high standards, fear of commitment, or an unwillingness to be authentic can hinder relationship success.

How can I tell if I’m the reason for my dating misfortunes?


Recurring rejection on initial dates might indicate a mismatch between expectations and reality. Sometimes, fixable issues like personal grooming, lack of interests, or financial instability play a role. Acknowledging and addressing these factors can be a turning point in your dating life.

Why do I keep choosing the wrong partners?


Picking unsuitable partners might be a pattern driven by subconscious motivations. It could be helpful to seek outside perspective, such as therapy, to understand underlying causes leading to repeated failed relationships.

Am I lying to myself about the kind of relationship I want?


Trying to fit a perceived ideal or societal norm can lead to dating a lot but finding it hard to establish a meaningful relationship. Authenticity is key. It’s crucial to align your dating approach with your true self to attract a compatible partner.

Is feeling sorry for myself affecting my dating life?


Self-pity and playing the victim can hinder relationships. It’s essential to take control of your life and avoid shifting blame to external factors. This attitude can repel potential partners and may necessitate a change in mindset or seeking support.

How to fix it

How can I change my dating fortunes starting now?


Recognize recurring patterns in failed relationships and seek professional guidance if needed. Take a critical look at self-care and emotional well-being. Embrace a positive mindset, be authentic, and work on self-worth to attract healthier relationships.

Can I overcome a streak of bad luck in dating?


Absolutely. Recognizing and addressing personal issues is the first step. With self-reflection, a willingness to change and perhaps seeking professional help, you can shift the dynamics of your dating life.

How can I identify my ideal partner for a successful relationship?


Take time off dating to define the qualities and traits you seek in an ideal partner. Understanding your needs and desires is crucial to attract a compatible match.

Can self-discovery improve my dating life?


Self-discovery plays a crucial role. Getting to know yourself better helps in building self-esteem and understanding your true worth, attracting partners who resonate with the authentic you.

What’s the key to a successful dating life?


The key lies in self-awareness, authenticity, and self-worth. Understanding oneself, being genuine, and valuing your worth paves the way for healthier and more fulfilling relationships.

For more help in fixing your bad dating patterns (or to get started with dating the right way), turn to our Mature Dating Game Plan – The Low-Stress Way to Find Your Soulmate After Divorce or Loss Without Getting Played.

Filed Under: Know Yourself, Sex and Romantic Relationships, Single Men Over 60

Previous Post: « I’m Single Over 60 and Still Work – Should I Date Someone at Work?
Next Post: Mature Women and Dating: Slogging Through the Dating Scene »

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