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About The Author


Emily Straubel

Emily is a sex and dating crusader. She founded The Red Lipstick Project as a place to talk openly about dating and sex and to connect with other intelligent women who want to find relationships that are as passionate and ambitious as they are. Emily also works with these women as a certified Holistic Health Coach to focus on their health and mindfulness as they go through breakups, job changes and other transitions to feel and look amazing in their own unique bodies. To share your story or experiences with dating in Portland email her at

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The Sex Files with Emily Straubel
Posted: January 19, 2015

Not ready to start dating again? Start dating again anyway

Start Before You're Ready | Red Lipstick Project | Sex Blog

When is it the right time to start a relationship?

Getting back out there in the dating world, especially when you’re coming back from a long-term relationship or a major heartbreak, can feel like trying to enter a roundabout with cars going 90 mph when you’re on a bicycle.

Timing is everything.

Finding the balance between jumping into a relationship too early and waiting until we’ve missed the boat is incredibly difficult and takes some serious emotional and sexual intelligence. I believe in the art of hesitation and the importance of a finely tuned gut check before jumping into bed or jumping into a relationship. But we often use that same hesitation as an excuse for not doing anything, and we become paralyzed in over-analyzing every detail of our potential romance.

This is not blanket advice that everyone should take. This is for the Type A over-thinker. The spreadsheet people. The people who’s notebooks are filled with pros and cons lists. You know who you are…

There are only two kinds of relationships that I consider complete failures:

  • Relationships that people stay in longer than is healthy.
  • Relationships that are never started in the first place.

Sometimes the only thing you can do in the insane world of dating is to start before you’re ready.

I work with clients all the time who want to be completely 100% ready to start a relationship before they approach a person they really like. Usually, by the time they do, that person has moved on and started a new relationship with someone else. Often times they want to be “totally over” someone before starting to date again. Other people are in a long-distance relationship and want to be 100% sure that everything is perfect before moving across the country to be with their love.

Guess what? You’ll never be “totally over” your ex. You’ll never be 100% sure things will work out. There is no certainty in love. But by not doing anything, you are ensuring that you’ll never have that same chance for love and happiness.

Here are a few reasons why starting before you’re ready makes sense:

Keep expectations low

When you start before you’re ready, you have a better understanding that things might not work out. You keep expectations low. You don’t put as much pressure on your partner to be perfect, because you know that you aren’t perfect either. Low expectations makes it easy to get into great relationships and let go of the ones that aren’t working as well.

Learn by experience, not by information

I hate to tell you this since you’re halfway through reading a blog post – but no blog or self-help book has the answers you need to finding and creating a phenomenal relationship. You can only learn about what works for you by actually being in a relationship and making mistakes. Blogs and books are a great way to spot-check your actions and make sure you’re on the right path, but you have to try and fail in order to figure out your relationship style and what partnership success is for you.

Don’t let yourself get bored

With all the pressure of getting into a relationship that we have built up as a culture (through online dating sites, marketing and advertising) we forget that finding a partner is actually pretty easy.When we think “the time is right” and we slowly ease into a relationship, we tend to think the work is done. It’s not. Once we are in a relationship – that’s when the work really starts. This is how people find themselves in PGRs (Pretty Good Relationships). It’s months or years before they realize that being unhappy in a relationship is as bad, or worse than being unhappy and single. When we start a relationship before we think we are 100% ready, people stay more vigilant and work harder to make sure they are bringing their best self to the relationship.

Failure is an option

“What if things don’t work out?” is a question that keeps people paralyzed in their singleness. Honestly, it probably won’t work out. But being able to recognize when things aren’t working and letting go of a relationship before it becomes toxic is my idea of a successful relationship!

Regret is the only failure

Taking chances and making commitments is how we push ourselves forward as awesome human beings. The only real failure is in not doing anything at all. Don’t let life happen to you – get out there and make mistakes. All relationships fail – until one finally works.

It’s okay to put your relationship on hold

It’s easier to start a relationship and put it on hold than to never start. Once you’ve done the groundwork of creating a connection you can take advantage of that chemistry and physical attraction and build a lasting relationship of any kind; friendship, partnership, etc. Maybe it’s not the right time for the two of you. So put things on hold and take some time as friends to work on yourselves.

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