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Things You Wish You Were Told About Dating: Advice from a Matchmaker

By: Tammi Pickle


Dating can feel like navigating a maze, where each turn could lead to bliss or heartbreak. We all wish we had a roadmap to guide us through the ups and downs of finding love. As a seasoned matchmaker with decades of experience, I’ve seen it all—heartwarming success stories, near-misses, and the pitfalls many stumble into. Whether you're new to dating or have been in the game for a while, this advice is designed to help you approach dating with confidence and clarity.


Be Yourself

One of the biggest mistakes you can make is pretending to be someone you’re not. Authenticity is the cornerstone of any lasting relationship. If you find yourself changing your personality to win someone over, you’re setting up the relationship on shaky ground. Remember, the right person will love you for who you truly are, quirks and all.


Become Best Friends

A successful relationship is built on friendship. It’s not just all about romance but about genuinely enjoying each other’s company. Share your passions, go on adventures, and create memories together. The bond you form as friends will make your relationship resilient and fulfilling.


Don’t Play Games

Games might keep things interesting in the short term, but they can also create a foundation of insecurity and mistrust. A healthy relationship should make you feel secure, valued, and respected. If you find yourself or your partner engaging in mind games, it’s time to rethink your approach.


Real Love Meets You in Your Mess

True love isn’t about being perfect; it’s about being real. The right partner will stand by you during your most challenging times, helping you navigate through stress and hardship. They won’t run at the first sign of trouble but will work with you to overcome obstacles together.


Know Your Wants and Deal Breakers

Before diving into a new relationship, take time to understand what you truly want in a partner. Identify your non-negotiables—those deal breakers that you simply can’t overlook. Whether it’s a desire for children, a commitment to marriage, or other core values, make sure you and your potential partner are aligned. It’s essential to get these conversations out of the way early on, so you don’t waste time on someone who isn’t on the same page.


Love Yourself First

Self-love isn’t just a buzzword; it’s a prerequisite for a healthy relationship. Before you seek out a partner, make sure you’re happy and content with who you are. Work through past traumas, learn from previous relationships, and enter the dating world as a complete, confident individual. A strong sense of self-worth will attract the right person into your life.


Trust the Timing

Timing is everything in relationships. Sometimes, the stars align, and everything falls into place effortlessly. Other times, it feels like the right person arrives at the wrong time. Trust that when it’s meant to be, it will be. When you’re truly ready, the right person will come into your life.


Perfection is a Myth

No one is perfect—not you, not your partner. Mistakes will happen, and it’s important to approach them with understanding and forgiveness. Learn to apologize when you’re wrong and to accept apologies with grace. Don’t dwell on past mistakes; instead, focus on building a brighter future together.


If It’s Too Hard, It’s Probably Not Right

Relationships shouldn’t feel like an endless uphill battle. If you’re constantly struggling or if your partner isn’t showing the commitment you need, it might be time to reassess. Love should be a source of joy and comfort, not constant stress and uncertainty.


Stay Positive and Optimistic

The dating world can be tough, but don’t let it bring you down. Stay positive and keep an optimistic outlook. Enjoy your life, spend time with friends and family, and trust that when the time is right, the right person will come along. Happiness is magnetic—when you’re living your best life, love has a way of finding you.


Don’t Ignore Red Flags

When someone shows you who they really are, believe them. Red flags are often early warnings of deeper issues. Don’t ignore them or make excuses for bad behavior. You deserve someone who respects and values you. Set your standards high and stick to them.


Avoid Jumping into Relationships Out of Loneliness

Loneliness can be a powerful motivator, but don’t let it push you into a relationship that isn’t right for you. It’s better to be alone and content than to be with someone just to fill a void. Make sure you’re entering relationships for the right reasons.


Learn from Past Relationships

Every relationship is a learning experience. Take time to reflect on what worked and what didn’t in your past relationships. Use those lessons to grow and to better understand what you need and want in your next relationship.


Communication, Listening, and Honesty

Effective communication is the bedrock of any successful relationship. Don’t bottle up your feelings—talk openly and honestly with your partner. Be a good listener, too. Understanding your partner’s perspective and needs is just as important as expressing your own. Together, you can navigate challenges and build a stronger bond.


Effort and Commitment

A strong relationship requires effort from both parties. Make sure you’re giving your all and that your partner is doing the same. Commitment means showing up for each other, even when it’s difficult. Invest in your relationship and watch it flourish.


Have Fun

Dating should be a joyful experience. Don’t take everything too seriously. Enjoy the process, go with the flow, and have fun. The journey to finding love can be just as rewarding as the destination.


 

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The views, information, and opinions published in this magazine or our blog are the sole responsibility of our contributors or interview subjects. Heart of Hollywood Magazine is not liable for any statements made, or information provided, by its contributors or sources.


 



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