In Loving

Jesse Dean Dennis

Mar. 10, 1987 – Sept. 28, 2019

Jesse Dean Dennis, 32, of North Chesterfield passed away September 28, 2019.

Jesse was a 2005 graduate of Freeman High School and a veteran of the United States Navy. He was the owner of First Class Glass and worked for RVA Tennis Courts.

Survivors include his children, Oliver and Finley and their mother, Caitlin; his oldest son, Sawyer and his mother, Kelly; father, Stephen Dennis (Sharon); mother, Wendy T. Martin (Michael); brother, Justin Dennis; sisters, Whitney Dennis, Leah Macchiarolo and Takika Bradley; paternal grandparents, Dean and Peggy Dennis; and maternal grandmother, Peggy Smith (Wayne). He was preceded in death by his grandfather, Kenneth Tomlinson. He is also survived by his girlfriend, Chatham.

A Celebration of Life will be held at 1pm Saturday, October 5 at Affinity Funeral Service Richmond Chapel, 2720 Enterprise Pkwy, Richmond, VA 23294.

Celebration of Life


Affinity Funeral Service

Richmond Chapel


Sat., October 5, 2019


1:00 P.M.

View Map & Directions




  1. Kimberly Asante September 30, 2019 at 3:14 pm - Reply

    My Jesse words can’t express how sad I am that you are no longer with me. I know you will always be with me in my heart you were and always will be one of my Kids. RIP “messy Jesse” We all at Assantes pizza miss your smile and laugh you’ve left a hole that will never be filled. Until I see you again soar with the angels watch over your sweet babies and all of us. We love you and you are missed ???

  2. Amy and David Gery September 30, 2019 at 7:13 pm - Reply

    Incredibly sad and heartbroken for our dear friends. We can only hope that someone who is struggling will take to heart that there is a path out of addiction. Prayers and love to the family and sweet babies.

  3. Jason Shaw September 30, 2019 at 8:26 pm - Reply

    I’ll be there

  4. Shannon Harris September 30, 2019 at 9:33 pm - Reply

    Jesse, I remember meeting you for the first time in English class our freshman year of highschool at Hermitage. You were absolutely funny, outgoing, the biggest smile that could’ve been seen for miles, kind and a true genuine person. Through the years we did lose contact but then you recently found me on facebook and we became friends just before you left us. I’m sorry we never got the chance to catch up but please know I pray that you are at peace, I pray for your loved ones that were left behind and I pray that your sweet babies aching hearts will mend and they grow up knowing how amazing you truly were.

  5. Kelly and Sawyer October 1, 2019 at 1:03 am - Reply

    I am truly devastated, Jess. I’m so glad our paths crossed and that we made a beautiful son together. You live on through Sawyer, and your two other beautiful babies. I’m so sorry it ended like this. I believe you are somewhere peaceful. Some place beyond what we left behind can comprehend. Please, check in with us if you can. Let us know you’re ok. I’ll be keeping my promise to you about Sawyer. Until we meet again. God bless you and your loved ones.

  6. DENISE VANN SPINDLER SEUTTER October 1, 2019 at 7:50 am - Reply

    My sincere condolences to you Sharon and your whole family. My prayers and thoughts are with you at this time. Sending you much love? I’m so sorry for your loss?

  7. Arlene Spencer October 1, 2019 at 8:46 pm - Reply

    So sorry his family has to go through this, may he Rest In Peace, and his family find comfort

  8. Chris Raines October 2, 2019 at 7:16 am - Reply

    I will be there

  9. Christian and Patty Spencer October 2, 2019 at 9:00 am - Reply

    So very sorry for your loss and your entire family is in our prayers

  10. Jerry Nicholas October 2, 2019 at 9:52 am - Reply

    I didn’t know Jesse, never met him, but I know his Mother Wendy, and his Grand Father Kenneth Tomlinson. Both were and are very good people, so I’m sure Jesse was a very good person also. I really feel for Wendy as i know she is grieving badly, but he will be with his Grand Father Kenneth, my friend from our Navy days, hopefully you can take comfort in this

  11. Caitlin, Oliver, and Finley October 2, 2019 at 6:51 pm - Reply

    I still can’t believe this is real Jesse. We created two of the smartest, funniest, most amazingly talented children together and I am forever grateful for our time together and these blessings. Our lives will not be the same without you but I promise to keep raising them in a way to make you proud and them the most loving, caring individuals they can be! We will love you always and I pray you are finally at peace.

  12. Kim Eggleston October 3, 2019 at 4:12 pm - Reply

    I am so sorry to hear about Jesse. Sending love and prayers to Wendy and the whole family.

  13. Debbie Lovette October 4, 2019 at 12:14 am - Reply

    To jesse’s family: I have known Jesse as Chatham’s dear friend for many years. As a parent, I cannot imagine the grief you feel. Jesse was light hearted and so friendly. My heart breaks for his children and for my daughter’s loss. God be with Jesse in a place where addiction does not exist.

  14. Sue J Adt October 4, 2019 at 3:18 am - Reply

    Wendy, I’m just so sorry that you too had to suffer the heartache of losing a child. There truly is no greater loss. I didn’t know Jesse, but you and I go back a long way. And, of course, I knew your dad Kenneth. Please know that you and your family are in my thoughts and prayers these coming days, weeks and months. Only time helps ease the pain.

    • John Becker October 16, 2019 at 8:14 pm - Reply

      I consider myself fortunate to have shared the years growing up with Jesse, whom I had considered my best friend for some time. Riding Go-Peds, playing baseball, sharing our excitement about the future, talking about girls we liked in school and laughing hysterically together; these are all vivid memories of mine. I was also fortunate to have known Jesse while we were kids because I was able to see in him the beautiful, brilliant, and true light that only another kids could have.

      Jesse was a pure, kind, hillarious person with an amazing soul. Regardless of the demons he may have fought, that kid I grew up with is who Jesse truly was and always will be.

      I love you Jesse. I’ll see you on the other side, brother.

  15. Jason Newcomb October 4, 2019 at 8:06 am - Reply

    Wendy I wish I could be there, the band has a wedding. We send our love & blessings to you and yours. ❤️

  16. Michele Powell October 4, 2019 at 7:47 pm - Reply

    I hope the Lord brings You, Mike, and Justin the much needed peace during this time. May God continue to bless you and keep you close.
    I will never forget Jesse’s kindness, music, and smile as he was growing up. He had great manners and was very respectful. I have great memories of us living next door to your Family and watching your sons grow up.
    My condolences to you and your family.

    Love ,The Powell Family

  17. Cindy and David Howell October 5, 2019 at 8:05 am - Reply

    Wendy, Mike and the rest of the family,
    Our hearts break for you!! We can’t imagine your pain!! It has been a long time since we have seen you and Jesse, but we remember so fondly the boys and baseball and the beach. We are praying for you all.
    Much love, David and Cindy Howell

  18. Teresa Martin October 5, 2019 at 10:22 pm - Reply

    Wendy, so sorry to hear of Jesse’s passing. Although I never met Jesse I remember all the times you spoke of him. May God keep you and your family strong through this difficult time. Love, Terry Martin

  19. Al and Daniella Kyriakidesf October 11, 2019 at 12:07 am - Reply

    Sharon, we send you and your family our deepest sympathy. We simply cannot imagine your sorrow. May his sweet soul rest in peace and his beautiful spirit live always through his children. We love you and are always here for you ♥️
    All and Daniella

  20. Nancy Shewey October 27, 2019 at 12:59 am - Reply

    Dear Jesse’s Family, I was late learning of your tremendous loss. I am sorry that I was not with you at the service but you all are in my thoughts and prayers for comfort now and always. Love, Nancy Shewey

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