Cynthia Glass/Agent X

Peggy Carter

Sharon Carter

Bernie Rosenthal

Diamondback

Connie Ferarri

The Scarlet Witch

The first woman that Steve fell in love with was Lieutenant Cynthia Glass. Cynthia was a member of the Nazi party working directly for the villain known as the Red Skull, and was assigned to infiltrate the American Super-Soldier project during WWI. While a part of this project, she met and fell in love with project participant Steve Rogers. When the two came to occupied France (along with Bucky Barnes) to free the project's leader, she was revealed as a nazi agent. She defied her masters, and helped free Bucky so that he could help Captain America, who was fighting the Red Skull in front of Hitler and an audience of both Nazi's and prisoners. When German soldiers tried to kill an unarmed Captain America, Cynthia stepped in front of the bullet, sacrificing herself for him.

During the rest of World War II, Steve would also meet and fall for a OSI operative working with the French Underground in Paris; he never knew her name, but would later discover that she was Peggy Carter, the elder sister of Sharon Carter. Peggy suffered from various psychological problems after learning about Cap's apparent death in 1945. She received various treatments including the manipulation of Dr. Faustus. Cap freed Peggy from Faustus' care and Peggy eventually regained her mental bearings. She has since served as an Agent of Shield and on the staff of the Avengers.

After his sleep on the ice, Steve fell in love with Agent 13 of SHIELD, Sharon Carter. Sharon would be Steve's major romantic interest until her apparent death at the hands of Dr. Faustus' catspawn, the Grand Director. However, cut off from SHIELD, Sharon became a freelance espionage agent, ultimately resurfacing and rejoining SHIELD, serving for a time as its Executive Director. Her relationship with Steve is currently undecided as regarding romance, although the two remain allies and close friends.

Some time after Sharon's death, Steve would meet Bernie Rosenthal. Bernie was a college buddy of Steve's neighbors Josh and Mike, and while she was in college a bit of an activist. She graduated, and over time became a professional glass-blower. Steve and Bernie's relationship developed slowly, in part because Steve kept disappearing on her, being called into action as Captain America.

While dating Steve, she attends a counter-demonstration led by her ex-husband, who is still an activist with the Jewish Defense League. Things between the Nazis and the anti-Nazi protestors become violent, and Captain America was forced to intervene. Listening to his voice and his words, Bernie comes to the inescapable conclusion that Steve Rogers is Captain America.

Bernie ultimately proposes to Steve Rogers, who accepts - however, when a downturn in the economy Bernie decides to go back to law school, but out-of-state. She and Steve put their romantic relationship and engagement on hold, and eventually end their engagement.

After she obtained her degree and passed the NY state bar, Bernie returned while Steve was involved with Diamondback. Bernie would serve as legal cousel for Diamondback regarding her murder of Snapdragon, and assist Steve in establishing the Hotline and its funding foundation. She has not been seen since Steve returned from the Franklinverse

Steve first met Diamondback when she was a member of the Serpent Society. Rachel Leighton fell in with a bad element in her youth, and eventually found her way to one of the Taskmaster's training schools. Outfitted by the Tinkerer, she was one of Sidewinder's first recruits for his team of snake-themed criminals. As part of the Serpent Society, she twice had occassion to kill Captain America, but refused both times. Later, she left the Serpent Society entirely so that she could pursue a romantic relationship with Captain America, and their relationship grew serious over time.

During her captivity at the hands of the Red Skull and Crossbones, they experimented on her with a blood transfusion from Captain America's blood, giving her an infusion of Super-Soldier blood, and boosting her physical abilities to a level with Captain America. She and Steve drifted apart when she made a deal with Superia to develop an antidote for the degenerative effects of the Super-Soldier formula for Cap, and he vanished after Onslaught before they could be reconciled.

After Captain America disappeared she has since aided Siren against the Taskmaster. Recently she was infected with mind-control nanoprobes and sent to steal information from the V-Battallion; in this conflict the ruthless Citizen V fried the nanoprobes in such a way that her central nervous system was severely damaged. However, given the Super-Solder Formula in her blood, it should slowly repair the damage and restore her to normal.

After Onslaught, Steve briefly dated Connie Ferrari, a defense attorney in New York City. However, when she discovered he was Captain America, she broke off the relationship. Since his apparent death and return after 911, he was fallen in love with an Atlantean agent of Namor's who was killed in action, dated an artist, was ensorcelled by the Scarlet Witch, and slept with a Diamondback LMD.