1) Ditzy and her high school sweetheart, one Royal Pin, AKA Pokey Pierce. Ditzy and Pokey dated through high school, and they were quite happy together. Ditzy, being naive and a bit clingy, thought her and Pokey were gonna stay together forever and get married. She was truly heartbroken when Pokey told her that he wanted to break things off before graduation, telling her that he wanted to go to Canterlot and open up a body-mod shop. Not too long after he left did Ditzy realize that she was pregnant. She had Dinky, and got a job delivering Mail in Ponyville. Pokey's dreams of entrepreneurship fell through and he came home not long after. He has no real relationship with Dinky and doesn't really make any effort to have one.
1.5) a little space-filler doodle of a younger Ditzy! Ditzy, while a little clumsy and naive, is a fully capable pony. She has autism and a lazy eye, leading many ponies who don't know better to assume that she is disabled in some way. Her Left eye (viewers right) is normal and her right eye drifts up and inward. Her vision is slight impaired and she has poor depth perception, but nothing that a pair of corrective lenses wont help, which she gets once shes older.
2) After Dinky gets her cutie mark and starts middle school, Ditzy reenters the dating scene after a decade-long dry spell. She eventually goes on a few dates with the new guy in town, Spearhead. Its not very serious and they both agree to call it off after a few dates. Unfortunately for Ditzy, those dates, which more often than not ended with a sleepover at his place, resulted in a pregnancy. Ditzy, deciding that she wants another child, keeps the baby and does not tell Spearhead. Her friend Time Turner is invaluable to her at this time, with his loosey-goosey work schedule allowing him to be there for her in the later trimester and make sure Dinky was well looked after when Ditzy was out at doctors appointments and prenatal classes. Time Turner is even there in the delivery room and did his very best not to faint. Time Turner is actually the godfather of all Ditzy's children, and Ditzy will be the godmother of Timeturner's kids if the nerd ever gets a date.
3) Ditzy's second born, a little colt named Chain Mail, was a medically complicated child. He was born prematurely and was in the NICU for the first month of his life. Nurse Redheart was there all hours of the day to help care for the colt, and Ditzy was eternally grateful to the white mare for teaching her how to care for her delicate son. Ditzy was deeply embarrassed to develop a crush on the nurse who cared for her newborn, but she soon found out that Redheart felt the same. In any other world it would be taboo for a doctor to fall in love with someone under their care (in this scenario the parent for someone under their care) but in Equestria, where pediatric and obstetrics doctors are more akin to midwives and wet nurses, there is less of a taboo.
4) After his stint in the NICU, Chain Mail grew up to be a healthy boy. He had his father's enormous frame and his mother's kind heart. When Dinky was about 18 and Chin Mail was 10, Redheart and Ditzy get hitched. With the help of a sperm donor, Redheart carried and gave birth to the couple's final child, a little filly named Booboo Kisses. It is around this time that Ditzy finally gets glasses to help with her vision, which has only gotten worse with age. It is also at this time that Twilight grants her the Equestrian Medal of Honor for her bravery during the attack on Canterlot by the Storm King, where she was temporarily turned to crystal while trying to protect the princesses. This honor also comes with a government check each month that keeps Ditzy and her family comfortable for the rest of their days.
5) meet the kids!! (left to right)
Booboo Kisses (she/her, cis, bisexual) Special talent: Children's Therapy
Chain Mail (he/him, nonbinary man, gay) Special Talent: mail delivery
Dinky Doo (she/her, cis, lesbian) Special Talent: magic