It has been well over 13 years since Jenelle Evans made her MTV debut in the 16 & Pregnant Season 2 premiere episode. Starcasm’s first article about Jenelle appeared just before her episode aired and featured a video of Jenelle and her bestie Tori smoking pot to MIA’s “Paper Airplanes.”
Since that initial article in February of 2010, Starcasm was there for all of Jenelle’s many relationships over the years — to the tune of more than 875 articles.
In the interest of pop culture history, and also to assist with any future Investigation Discovery documentaries, we’ve combed the Starcasm archives and put together a comprehensive Jenelle Evans dating timeline.
The photo above is a quick reference showing all of the men Jenelle has dated (that we know of) since she was sixteen and pregnant. Below is a more detailed timeline that includes some other events in Jenelle’s life, such as births and arrests.
* This timeline was initially compiled in November of 2017 when it was announced MTV would be airing an “Ex Files” special featuring old Teen Mom 2 footage and new interviews with most of Jenelle’s exes. Since that time, Jenelle and husband David Eason had an acrimonious split and reconciliation that included Jenelle briefly dating someone new. We have since updated the timeline and the graphic.
2006ish – Jenelle started dating Andrew Lewis
August 2, 2009 – Jace is born
??, 2009 – Jenelle breaks up with Andrew
February 16, 2010 – Jenelle’s episode of 16 & Pregnant premieres
??, 2010 – Jenelle starts dating Kieffer Delp
#TeenMom2 Jenelle's ex Kieffer Delp was paroled last week after serving 2+ years for running a meth lab in his basement apartment! 🥳 ….and was arrested for bail jumping 6 days later. 🙁 https://t.co/5PoVoRBVTl
— Starcasm (@starcasm) February 25, 2020
January 13, 2011 – Breaks up with Kieffer Delp
January 15, 2011 – Jenelle and Kieffer spotted together again
??, 2011 – Jenelle and Kieffer begin a string of break ups and reconciliations that even we couldn’t keep up with (though we did try) The constant relationship shifting inspired us to create the Jeniefferometer:
May 23, 2011 – Jenelle breaks up with Kieffer Delp
??, 2011 – At some point around this time, Jenelle started dating Josh Miller. The relationship moved quickly with Jenelle actually moving in with him prior to the relationship falling apart.
January, 2012 – Jenelle starts dating Gary Head
April, 2012 – Jenelle breaks up with Gary Head
May 4, 2012 – Jenelle breaks up with Kieffer Delp, Kieffer shares ripped up love poem and drawing he made for her
May, 2012 – Jenelle starts dating Gary Head again
May 15, 2012 – Jenelle gets engaged to Gary Head
— Starcasm (@starcasm) April 23, 2013
July 19, 2012 – Jenelle officially gets back together with Kieffer Delp (again)
September, 2012 – Jenelle heads to New Jersey to be with Kieffer
September 28, 2012 – The New Jersey trip does not work out, Jenelle breaks up with Kieffer and heads back to the NC
October, 2012 – Jenelle begins dating Courtland Rogers
October 14, 2012 – Jenelle breaks up with Courtland Rogers
October, 2012 – Jenelle and Courtland reconcile, move in together
— Starcasm (@starcasm) October 10, 2012
November 19, 2012 – Jenelle gets engaged to Courtland Rogers
December 4, 2012 – Jenelle marries Courtland Rogers (There were reports that Jenelle was pregnant at the time)
January 16, 2012 – Jenelle announces that she is pregnant with Courtland’s baby
January, 2013 – Jenelle breaks up with Courtland, files assault charges against him
January 25, 2013 – Jenelle suffers a miscarriage
January 26, 2013 – Jenelle appears to be back with Gary Head
February, 2013 – Jenelle breaks up with Gary Head
March 13, 2013 – Jenelle gets back together with Courtland Rogers
April 23, 2013 – Jenelle and Courtland arrested on assault and drug charges (Things got crazier than usual after their arrests — click the link for a timeline)
Dates & details on all four of Courtland Rogers' alleged assaults against Jenelle Evans http://t.co/YtFMcbSyu7 With photos of the warrants
— Starcasm (@starcasm) March 7, 2013
June 3, 2013 – Jenelle meets Nathan Griffith in person for the first time
Mid-June, 2013 – Jenelle moves in with Nathan in Myrtle Beach, SC
June ??, 2013 [estimate] – Jenelle has an abortion (Courtland found out about the abortion from watching a Teen Mom 2 preview)
December 11, 2013 – Jenelle announces she is pregnant with Kaiser
December 14, 2013 – Jenelle arrested after altercation with Nathan
May, 2014 – Jenelle files for divorce from Courtland Rogers
June 10, 2014 – Jenelle’s divorce from Courtland Rogers finalized
June 29, 2014 – Kaiser is born
January 6, 2015 – Jenelle gets engaged to Nathan Griffith
January 29, 2015 – Jenelle and Nathan break up
?? 2015 – Jenelle and Nathan get back together
March 4, 2015 – Nathan Griffith arrested for domestic violence against Jenelle
— Starcasm (@starcasm) August 20, 2015
May 23, 2015 – Jenelle and Nathan spotted together in New Jersey
May 28, 2015 – Jenelle turns herself in to police after Nathan filed a domestic violence charge against her
June, 2015 – Jenelle and Nathan get back together
August 3, 2015 – Jenelle and Nathan break up
September 21, 2015 – Jenelle starts dating David Eason
April, 2016 – Jenelle suffers a miscarriage
January 24, 2017 – Ensley is born
February 11, 2017 – Jenelle gets engaged to David Eason
September 23, 2017 – Jenelle marries David Eason
October, 2019 – Jenelle leaves David and relocates with the kids in Nashville, Tennessee. She takes a restraining order out on David citing that she was afraid for her safety and the safety of her kids. It was later revealed that Nathan Griffith’s mother Doris was in Nashville and helped Jenelle with taking care of the children.
December, 2019 – Jenelle flies to Massachusetts to hook up with Herbert “Herbie” Wilkinson, who previously appeared on MTV’s Is She Really Going Out With Him? as an assclown from Massachusetts dubbed “Massclown.” Jenelle and Herbie DID NOT hit it off, and the two eventually trashed each other on social media.
January, 2020 – Jenelle drops the restraining order against David and the two are spotted hanging out being chummy together in Nashville. Jenelle and David would later return to The Land together to live out their happily ever after once and for all.