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30 Dating Dilemmas in 30 Days – Rachel Astarte

Your favourite milf dating site, Toyboy Warehouse has 30 days to gather the most influential dating and relationship experts to help answer 30 dating dilemmas from real members. It’s a race against time to solve the world’s love issues, will we make it?

About you

Tell us about yourself

I am a psychotherapist, transformational life coach, author, and educator in the New York City area. I am the author of Celebrating Solitude: How to Discover and Honor Your Highest Self.

If someone came to you for dating/relationship advice, what should they expect?

A client interested in dating and relationship advice can be sure that we will begin with the only thing we can begin with: him- or herself. Development of the self is essential before we can enter into a relationship with another person.

What are some of the projects you’re currently working on?

Aside from seeing clients, I’m spending much of my time writing and producing my new podcast, Self Talk with Rachel Astarte (

Dating Dilemmas

Name: Derrick

Age: 40

Gender: Male

“I’m about to become divorced? How difficult is it for a divorced guy to get back into dating. I’m starting to get nervous that things will be pretty difficult for me.”

Be sure you’re ready. Spend as much time as you need to get to know yourself—what you want and don’t want in the next relationship. Never feel pressured to get back into the dating world. When you are ready, you will know.

Name: Anonymous

Age: 39

Gender: Female

“What would you recommend for someone who’s really shy but would love to be dating?”

What does shy mean to you? Do you feel insecure about who you are or are you simply particular about the company you keep? If it’s the former, spend some time celebrating your life just as it is. There is no one exactly like you in all the world. That’s pretty amazing. Confidence in that knowledge is very attractive. If it’s the latter, accept that you will need to be discerning about the people you choose to date. Nothing wrong with that. Trust your instincts.

Name: Martin

Age: 21

Gender: Male

“I’ve never been on a proper first date in my life. I’ve had girlfriends but I’ve never had an official first date. Help.”

It helps to think of dating as a kind of social club. Throw away all expectations of what you might want from the date, and settle into getting to know that fellow human being who’s chosen to spend time with you. That’s enriching all by itself.

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