Inspire U: The Podcast

Dating in Your 30s: How to Date Fearlessly

By Nicole Glassman for

We use swimmies to learn to wade in the big kid’s pool. We use training wheels, we wear a helmet, and we tie our shoes in double knots, all so that we don’t trip and fall.

But what happens to those protective shields when we grow up?

As adults, we take risks without warning and we have to pick ourselves up when we fall. We cross the street before the light changes. We drive without seatbelts and we change lanes without signaling. We wear stilettos on slick streets and we go into the cold without enough layers.

And when it comes to love, there’s no one there to help us cope with our fears of rejection, or to hold our hand when we are starting a new relationship. There is no one there to protect our heart or to tell us to love with abandon; no seatbelt to guard our spirit, no perfect training wheels for a new relationship and no shield big enough to protect our heart. Dating is complicated, and in your thirties, it can be even more overwhelming.

Dating in your thirties is the complete opposite of dating in your twenties. In your early twenties everything seems casual and carefree. You aren’t thinking about marriage and long-term compatibility. You don’t have nearly as much baggage and your life is less complicated. Many of your friends are single and you don’t feel the pressure to settle down.

But when you date in your thirties there is more risk; you have most likely been hurt and disappointed and you are afraid. You are most likely looking for a partner, but your life is much busier. You have more criteria but less patience and far less time. If you make time for a date it had better be worth it and there is less room for mistakes. If he doesn’t call when he says he will, you give up. If he makes one wrong move, your guard is up. You swear you will never be hurt again and that you would rather be alone than settle.

You promise yourself that you will wait for the right man, that you won’t settle, and so, you continue to date. But when you meet a possibility, your fears take over and you wonder if you have the strength to jump in once again, or if you’ll allow yourself to lose control. You hate being thirty and knowing that you don’t want to waste your time.

What are we really afraid of?

One common answer is rejection. As one woman, Amanda, says, “I am terrified that this relationship will end and that it was all for nothing. I mean how many times can you start over? Who has the time or the stamina?”

Another common fear is repeating past mistakes with a new relationship. Another dater, Laura, who had been treated badly in the past, expressed her fear of meeting another liar. “My last boyfriend had a double life. It seemed he was devoted and wonderful to me. Then I found out that I was one of many women in his life. I was devastated. How can I ever trust again?”

Relationships challenge us and help us to mature. Oftentimes, they act as a mirror, highlighting the changes we need to make in our own life and the lessons we need to learn. Maybe the last guy we dated cheated and we were “too trusting” or maybe he was a “commitment-phobe.” Maybe we jumped in too soon or maybe you just weren’t right for each other. The truth is we have all been through something that has made us more guarded than we may want to be. But avoiding a potential wound will not protect your heart. It will only shut down your ability to love and to grow.

The key is finding the lesson in that past hurt and learning something from it. Don’t focus on the fact that you were cheated on and that no one will ever love you again. Focus on better communication and finding someone where both of your needs will be met. That relationship made you stronger. We have all suffered and yet, we have all survived. The truth is, when you meet someone worthwhile you will take that risk and you should be fearless in your relationships, and you’ll find what you are looking for.

How to date fearlessly

1. Remember you aren’t the only one who has been hurt: The guy you’re with has probably been hurt at some point in his life too, and he’s just as afraid as you are. Just remember that you lived through your past hurt. We are all afraid of repeating our mistakes and jumping in too soon – but we are not alone in that fear.

2. Throw out the timeline: There is no right time to “have the talk.”There is no perfect time to have sex. There is no perfect time to say, “I love you.” There is no ideal time to get married. The perfect time is a personal decision. Don’t rush things because you feel they should be a certain way.

3. Be patient and trust: Everyone dates at a different pace and it may take time for both of you to feel comfortable and to really be yourselves. It also may take time to open up. Take a deep breath and keep things in perspective.

4. Believe you deserve to be in a successful relationship: This is key. Your thoughts are powerful and as long as you believe you will never find happiness or that you don’t deserve a loving partner, this will be your reality.

5. Keep your life full and have fun: Don’t make him everything – especially in the beginning. You had a life before him and that is attractive. Keep your support system close by. Your friends are the people who will always be in your life.

Also On Hot 96.3: