Peter Parker / Spider-Man

Main Comics (616)
1.  Betty Brant  - J. Jonah Jameson's secretary was Peter's first girlfriend. After they broke up, she married Ned Leeds, although she was later widowed. She and Peter have remained close friends ever since

Spider-Man once asked the engaged celebrity superhero Invisible Woman out and, to make Reed Richards angry, she accepted. They apparently went on one lighthearted date, even with his secret identity remaining intact..

2.  Gwen Stacy  was Peter's college girlfriend, and his first love, murdered by the Green Goblin. He later found out that, during a time off in their relationship when she was in Europe, she had slept with that same man, Norman Osborn, gotten pregnant, and given birth to twins, before returning home.

Mary Jane is the niece of Peter's Aunt May's best friend Anna Watson. They had been trying to set them up for ages, but around the time they finally met, Peter was forming a relationship with Gwen Stacy. The two became good friends, as did Mary Jane with Gwen, and she even briefly dated Peter's best friend, Harry Osborne.

Gwen Stacy was killed at the hands of the Green Goblin.

3.  Mary Jane Watson  - After Gwen's death, however, Peter and Mary Jane's relationship began to turn romantic. They dated for some time before breaking up.

At some point, Betty Brant and her husband Ned were separated, during which time she threw herself at Peter. However, nothing came of it (ASM #186, 1978)

Spider-Man also fell for The Black Widow, before realizing that the personality he had fallen for, Nancy Rushman, was actually a false identity that had arisen in Black Widow. (Marvel Team-Up #82, Jun. 1979)

4. Cissy Ironwood and Peter dated for a time (Marvel Team-Up Annual #2, Oct. 1979)

5.  Debra Whitman  was another love interest in the 1970s.

6.  Felicia Hardy / Black Cat  - Peter and Felicia dated while both carried on double lives as costumed adventurers. (ASM #194, Jul.1979)

At some point they learned each other's secret identities, and were still involved for a time, before breaking up.

Peter and Mary Jane eventually got back together and were married.

Peter and his friend Betty Brant apparently did kiss during this time. (Web of Spider-Man #91, 1992)

Mary Jane became pregnant, but due to her being poisoned by the Green Goblin, the baby, a girl named May, was stillborn. (ASM #418, 1996)

Peter was also the object of the affections of Mattie Franklin, AKA Spider-Woman. (ASM v2 14, 2000)

7. Jill Stacy - During a time when Peter thought MJ was dead, he dated Gwen Stacy's cousin Jill. (Spider-Man #76, Nov. 1996)

7.  Caryn Eagle  and Peter dated during a period of estrangement from Mary Jane. (Peter Parker: Spider-Man v2 #30, 2001)

He and MJ later reconciled.

In order to save the life of his Aunt May, Peter and Mary Jane made a deal with the demon Mephisto, whereby his entire marriage to Mary Jane was forgotten by everyone, and the two were no longer together. (ASM #545, 2008)

8. Carol Danvers / Captain Marve l and Peter have become friends through their adventures (Dark Reign, 2008-09), and he once asked her out on a date, which she accepted (Ms. Marvel v2 #34, Feb. 2009)

In the meantime, Peter once took his acquaintance, Michelle Gonzalez, to a wedding, even though they had trouble getting along. There, she encouraged him to go talk to Mary Jane. However, the next morning, Peter awoke to find he had spent the night with Michelle, and didn't remember it. An enraged Michelle kicked him out. (ASM #600-601, Sept.-Oct. 2009)

Shortly after, he sleeps with Felicia again. (ASM #606-607, Nov. 2009)

9.  Hebe  This Greek godess, the wife of Hercules, and Peter, kissed once, enraging Hercules. (Assault on New Olympus, Jan. 2010)

Finally, he and Carol have their first and only date (Ms. Marvel v2 #47, Jan. 2010)

Carol has since expressed feelings for him. ( Siege: Spider-Man, Jun. 2010)

10.  Anna Marie Raven / Rogue  and Peter almost kissed once, before being interrupted. (X-Men Forever 2 #3, Sept. 2010)

11.  Carly Cooper  later became Peter's girlfriend (ASM #647, Nov. 2010)

12.  Lian Tang ,is a designer at the Shanghai branch of Parker Industries. She co-designed the latest Spider-Mobile with Peter Parker. While she and Peter are in an intimate relationship, she disapproves of Spider-Man's apparent insubordination, not knowing he and Peter are one and the same. (ASM v4 #1)

She is in league with Scorpio, leader of the Zodiac, providing him Parker Industries' security codes in exchange for medication for her mother, who was sick with cancer. When Scorpio threatened to have her disposed of as a loose end, she offered to kill Spider-Man for him in exchange for medication. She attempts to kill Spider-Man during Shen Quinghao's award ceremony, but cannot go through with it. After learning the circumstances behind her attempted betrayal, Spider-Man forgives her and asks that she help him take Zodiac down (Amazing Spider-Man v4 #6-8)

When Superior Octopus and Hydra targeted Parker Industries, Shanghai Branch, Lian Tang became Spider-Rider to help Spider-Man fight them (ASM v4 #30, Sept. 2017)

Under the influence of her pheremones, Peter came close to having sex with Cindy Moon, AKA Silk, twice, being interrupted both times. (ASM v3 #4, Sept. 2014)

13.  Bobbi Morse / Mockingbird  and Peter later dated.

14. Rebecca London

 

Ultimate
1.  Kitty Pryde  - These two have been in a relationship

1967 Animated Series

 * 1)  Betty Brant 

1981 animated series

 * 1)  Betty Brant 
 * 2)  Medusa 

Spider-Man and His Amazing Friends

 * 1)  Ariel 

Film Trilogy (2004-07) (also MTV animated series)

 * 1)  Mary Jane Watson 

Amazing Spider-Man Films (2012-14)

 * 1)  Gwen Stacy 

Spectacular Spider-Man

 * 1) Liz Allen

Spider-Man (PS4 Universe)

 * 1)  Felicia Hardy / Black Cat  (The Black Cat Strikes)

Marvel Cinematic Universe

 * 1)  Liz Toomes 
 * 2)  Michelle "MJ" Jones