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30 Dating Dilemmas in 30 Days – Samantha A. Gregory

Your favourite dating older women 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 the author of, No More Crumbs: How to Stop Dating (and Mating) for Crumbs and Get the Cake You Deserve in 10 Crucial Steps. I am also a relationship recovery coach at who helps women recognize, reject, and release toxic people so they can recognize their worth, embrace their feminine power, and attract healthy love (and wealth).

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

If someone came to me for dating or relationship advice, they can expect a listening ear, compassionate heart, and frequent reality checks. I believe in helping people face their truth and focus on becoming the best version of themselves.

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

I am working on the 2020 version of No More Crumbs, which will include learning how to navigate modern dating practices, more feminine empowerment advice, and interactive features that allow the reader to view related videos.

Dating Dilemmas

Name: Anonymous

Age: 25

Gender: Male

“Can a guy in his 20’s who’s also divorced find love? Because the answer so far has been no”

I believe anyone can find love despite past relationship issues/problems. The key is to first find love inside your own heart and fill every aspect of your life with love. Deal with issues from your past relationship and forgive you ex and yourself. Love sometimes feels elusive because you haven’t dealt with the painful divorce and are seeking a relationship to distract you from the healing work that needs to be done. 

Name: Anonymous

Age: 39

Gender: Female

“I’m on a streak of 7 bad dates, I’ve got my eighth in a couple of weeks. What can I do to make sure this doesn’t make it 8 bad dates? Is there anything I can do?”

A streak of bad dates is a clue that there is something going on with you. You are the common denominator in each scenario. Take time to review the dates and your behavior to pinpoint how you have possibly sabotaged your dates. If you are going in thinking it will be a bad date, you are getting what you are expecting. Try imagining this 8th date is the best you’ve ever been on and go with that good feeling. See how it goes. If it’s still bad, consider you may be choosing or agreeing to dates with incompatible people because you are not really ready to meet a good guy.

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