174: Tripp Kramer: From Shy To Dating Mastery

Tripp Kramer is the founder and CEO of the Tripp Advice podcast and blog, a resource for men to help them take their sex and dating lives to the next level.

Tripp was a traditional shy guy who decided to tackle his challenges with women head on. After years of practice and rejection, Tripp has devoted his life to helping other men have thriving dating lives through his eBooks, online courses, coaching and podcasting.

Favorite Success Quote

“Successful people do what unsuccessful people are unwilling to do”~Jeff Olson

Key Points

1. You Will Have to do Crazy Shit to Succeed 

Whatever your goals are, you will probably have to do crazy shit to achieve them.

To improve his dating life, Tripp spent months of going out every night to meet and flirt with girls until he successfully went from “shy guy” to “ladies man” approaching women and having conversations he never thought he could do.

Whether you want to improve your dating life, run your own business, or master your health, you will have to do things that scare you shitless to get there.

You will have to put in the work, you will have to lose sleep, you will have to bust your ass… but it will be worth it.

2. The Worst Isn’t that Bad 

When most guys start the process of getting better with women, they are scared to death of rejection. They are scared of getting slapped or getting a drink spilled on them, but in reality, the worst that will happen probably isn’t that bad.

In his years of approaching and dating women, Tripp’s worst rejection was merely a girl walking away from him in the middle of a conversation.

Chances are, the things that terrify you aren’t even close to reality. Failure is not as bad as you may imagine it, so get out there and just start. The worst that can happen isn’t that bad.

3. You Learn to Manage Fear… Not Eliminate it

A mistake that many guys make is to think that they will one day completely eliminate fear from their romantic lives…simply put you won’t.

You learn to manage fear, to accept fear for what it is and see it as a call to action.  So learn to feel the fear and do it anyways, if you aren’t a little scared you aren’t growing!

As JFK said “There is nothing to fear but fear itself.”

4. Train Yourself to Regret Inaction More than Failure

Remember the old quote that “You miss 100% of the shots you don’t take?” Well that is doubly true with dating and approaching women.

You must train yourself to make the pain of not taking action, more painful than your fear of rejection. Realize that every woman you meet, could be the love of your life.

If you do not take action, you could have missed out on one of the greatest romantic experiences of your life. Learn to make this feeling more painful than any slap in the face could ever be.

5. Take Baby Steps 

Some guys will have no issue going out and immediately approaching and talking to women, but for others, merely holding eye contact with a girl is enough to make them nervous.

Wherever you are, learn to take baby steps and master this skill a little at a time. The general progression goes something like this.

Going Out:

In the beginning, just go out to bars and clubs or any other venue and just get comfortable being in these locations by yourself. If you want to talk to other people or meet women, great! But for starters, just focus on getting out there.

Eye Contact:

After you get comfortable being in these new venues, start looking girls in the eyes when you walk by them and flashing a quick smile. Don’t worry about saying hello or getting a number, just make eye contact and consider it a win.

Start an Indirect Conversation:

Now that you are getting more comfortable at venues, and starting to be ok around women, begin starting indirect conversations. Innocent things like asking for an opinion on something, asking for directions and simply saying hi.

Direct Openers:

Once you are comfortable starting and holding conversations with women about random events or other topics, start being bold and forth right about your intentions. Walk up to those girls and let them know that you find them beautiful and want to get to know them better.

Keep in mind that when you are starting these direct conversations there are a few things you can do to accelerate the interaction.

Stance: Stand in front of her with good posture and your shoulders slightly angled towards her, not parallel to hers.

Eye Contact: When you are speaking or listening, keep consistent eye contact and smile

Listen: Actually listen to what she has to say and show interest in her and her life.

Physical Escalation:

Now it’s time to get physical! Go in for a sexy high five (a normal high five that you hold for just a second longer than you would high fiving a guy friend).

Touch her on her lower back, get close and whisper something to her, twirl her around, do anything you can to break the touch barrier in a fun and non creepy way.


Now that you are comfortable appraching, talking to, and getting physical with a girl, it’s time to seal the deal. This is the part of the interaction where you get her number, invite her on a date or head back to your place for drinks.

If you have really mastered everything up to this point, this can actually be one of the easiest parts of the whole interaction (give that she is attracted to you)

6. Getting Good With Women is a Gateway Drug to Success

If you can get good with women, you can do anything. Use your experience of mastering your dating life as a catalyst to master other areas of your life.

Tripp realized after getting good with women that he wasn’t fulfilled in his 9-5 and wanted to start his own business focused on his passion of helping men master their romantic lives… Thus Trippadvice was born.

Go out there and master your love life, and then use that success as a way to achieve massive success in all other areas of your life.

Influential Books

1. A Billion Wicked Thoughts by Ogi Ogas & Sai Gaddam

2. The Millionaire Fastlane by M.J. DeMarco

3. The Power of Now by Eckhart Tolle

Connect With Tripp Kramer


Next Steps

We’re on a mission to impact a million men with powerful life changing content. If you enjoyed this article, please share it with your friends on your preferred social network on the left. I spent a ridiculous amount of time creating this article for you and with your support, we can impact the world together.

Want to become the strongest version of yourself?

Then click here to get a free trial to my elite community of 800+ high-performing men, The Secrets of the Top 1% of Men. Not only will you get tapped into your own “band of brothers”, but you’ll also have access to some of my best content and training as well as bi-weekly group calls with my team of coaches.

If you’re ready to push the boundaries of what’s possible in your life and become the man you’ve always wanted to be. This is the fastest way to do it.

The Times Have Changed. This is the Way Forward in 2024.

Here’s how I can help in my new FREE training on becoming a stronger Grounded Man:

1. The new path for men that creates a purpose driven life and doesn’t require you to lose your personal power, put women on a pedestal or sacrifice your goals.

2. Why men consistently settle and ignore the most important areas of life like the quality of their intimate relationships, social life and happiness and how to optimize all three without sacrificing professional growth.

3. The biggest mistake 97% of men make that breeds loneliness, breakups and emasculation that is absolutely reversible with this counter intuitive strategy.