8: If I Was Single Again…


What would you do if you were single again?


Have you ever given it any thought?


Are there things you miss about being single?


Are there things you would have done differently?


While you ponder those questions, listen to the amazing discussion I had with Sherley and Jackie on the podcast episode, ‘If I Was Single Again…’:



If you enjoyed this podcast, click to tweet and share it with others!




Episode Title: If I Was Single Again…


Guest: SherleyFollow her on Twitter * JackieFollow him on Twitter


Music: KeithDopeMusic – STONE & WATER * Leon Timbo – What Took You So Long *

Mario – R.E.A.L.L.Y. Love You



“Confession is good for the soul, but bad for the rep.” – Jackie


“Married life will provide everything that single life does, plus more!” – Jackie


“I would feel sorry for a guy to be with me…he’d have to do some Cirque Du Soleil type stuff to prove his love.” – Sherley


“Being in a long-term relationship has really challenged me in understanding more and more of myself.” – Sherley


“Be weary fellas of girls who go from relationship to relationship.” – Sherley


“People ask, ‘When is the right time to start something?’ YESTERDAY!” – Jackie


Key Takeaways & Lessons:

  • The HUGE and SCARY impact that social media has on the dating scene
  • Jackie explains why it would be UGLY if he were single again and had to deal with social media
  • Sherley and Jackie express their concerns with their children getting involved on Facebook and Instagram
  • Sherley confesses that if she was on the dating scene now she would be DANGEROUS
  • Knowing who your partner’s relationship examples were is extremely important
  • Courage and vulnerability are two of the biggest hurdles to overcome before entering into a relationship
  • The power of learning from your mistakes


Experience is the Best Teacher:

  • Sherley shares why being in a relationship for over 20 years has made the concept of being single foreign for her
  • Sherley and Jackie explain why they don’t believe in having and OUT from their relationship and marriage
  • Sherley’s father put her up on game and it properly prepared her for dating
  • Sherley admits that going from relationship to relationship was a distraction for her, but it taught her a lot about herself
  • Find out what Sherley & Jackie would do if they were single again for 30 days


Call to Action:

  • Leave a comment below and let me know what you would do if you were single again. If you are single, tell me what you like/dislike most about being single.

*Please use the contact form if you don’t feel comfortable leaving a comment below and sharing your answers publicly.*

  • Jackie Bledsoe, Jr.
    May 19, 2014

    Man, thanks again Jay for having me on the show! I enjoyed hanging out, and getting a chance to meet and chat with Sherley as well.

    Keep doing what you are doing and helping people build better relationships, Jay!

    • Jay
      May 19, 2014

      The pleasure was all mine Jackie. I truly enjoyed this discussion with you and Sherley. You both provided a wealth of knowledge and left me with some very important things to ponder.

      Thank you so much for that! I can’t wait to have another amazing discussion with you.

      Stay Blessed!

  • Chonilla
    May 20, 2014

    Thank you again Jay for having me on the show plus introducing me to Jackie and his world.

    It was an absolute pleasure talking to both of you. I love the approach of the show plus the concept. Keep pushing, you are doing an amazing job. In this world now of Gossip and World Star it is refreshing for people like myself and many others to hear content like yours. YEAH JAY!


    • Jay
      May 20, 2014

      WOW! You are far too kind Sherley. Thank you so much for the kind and encouraging words.

      I had such an amazing time with you and Jackie. I cannot wait to have you both back on the podcast again!

      It’s so great that not only do we have amazing discussions, but we meet and get to know such great people in the process. That’s one of the things I love most about podcasting.

      You have an outstanding show and network too! I pray that you and Clove have tremendous success with it!

      Thank you for your continued support and for being in my corner. It truly means a lot Sherley!

  • Jay
    May 21, 2014

    You’re right Don! “Me Time” is so important. I can’t even lie, if a woman doesn’t understand my need for time to myself…that’s likely to be a deal breaker.

    Thank you so much for listening to the podcast Don. I truly appreciate that and you taking the time to answer the question and share your thoughts. Thanks!

  • Anye
    December 28, 2015

    Great show and it really allow me to understand what I need to work on as a single woman. Also Sherley I am also Haitian and I struggle with giving control and being vulnerable when it comes to relationships.

    • Jay
      December 28, 2015

      Hey Anye! Thank you so much for listening!

      I am so glad you enjoyed the discussion with Sherley and Jackie.

      God bless you!

Write a Comment

Your email address will not be published. Required fields are marked *