1. Bobby Fischer and Barbra Streisand
Barbra Streisand, the future Emmy, Grammy, Oscar and Tony winner, actually attended the same Brooklyn high school as Bobby Fischer, who at the time was already competing in and winning international chess tournaments. Streisand later confided that she had a crush on the chess player, saying that he "was always alone and very peculiar. But I found him very sexy." And how did Fischer feel about her? In an interview with a Japanese radio station, Fischer said, "I remember some mousy looking girl."
In the end, the fact that Streisand's crush went unrequited was probably for the best. She went on to marry Elliott Gould and James Brolin, while Fischer disappeared from the public eye and eventually fled the country, wandering around Europe and Asia.
Interestingly, Streisand and Fischer were not the only notable alums of Erasmus High School. Among the other notable former students: Oakland Raiders owner Al Davis, Three Stooges member Moe Howard, actress Mae West and singer Neil Diamond. To our knowledge, none of them shared Streisand's romantic interest in Fischer.
2. William Rehnquist and Sandra Day O'Connor
It's amazing enough that one Stanford law school class produced two Supreme Court justices. It's even more amazing that the two of them dated. Despite their future differences, Sandra Day O'Connor and William Rehnquist actually struck up a good friendship while at Stanford Law and, according to later accounts, went on a few dates. In a biography by Ann Carey McFeatters, O'Connor recalled that the two "went to a few movies and one thing and another," adding that Rehnquist was "a star" on campus (he would later claim to be first in the class, although Stanford didn't rank students at the time).
Although their dates never resulted in history's only Supreme Court power couple, the friendship did pay off later. O'Connor's friendship with Rehnquist helped her elevate herself to a Supreme Court nominee and their families remained close until Rehnquist's death in 2005.
3. Jennifer Aniston and Jon Stewart
On a recent Daily Show appearance, Jennifer Aniston and Jon Stewart recalled an unsuccessful date they shared at an Italian restaurant as both were on the cusp of fame. Aniston was filming the first season of Friends at the time, while Stewart was developing a show for MTV and asked the actress out on a date. So, what went wrong?
“It was lovely,” Stewart said. “I remember you brought so many people ... and I remember thinking ‘she’s so excited to be on a date with me, she wants me to get to know her posse.’"
Aniston, meanwhile, remembered things a bit differently. She said the date had always been a group event to begin with, but that she didn't mean any offense to Stewart. The two never had a chance for a second date, whether in a group or not.
4. Elizabeth Bishop and Robert Lowell
This dream matchup of poets was actually close to becoming a reality: Robert Lowell was actually ready to propose to his friend and pen pal, Elizabeth Bishop. But circumstances got in the way: Bishop was living with a lover in Brazil, while Lowell was married to writer Elizabeth Hardwick. The two poets had met years earlier at a dinner party after Lowell had just won the Pulitzer Prize and Bishop said she "loved him at first sight." She later said "I remember thinking that it was the first time I had ever actually talked with some one about how one writes poetry."
Although they never married, the two had an intense relationship, revealed through a series of letters published in a 2008 collection called Words in Air. They were quick to praise the other's work and point out where it was succeeding: he liked her attention to detail, while she commended his use of his personal experience. The letters don't get into too much personal information, but did provide an outlet for the two poets to simply discuss their craft.
5. Condoleezza Rice and Gene Washington
Condoleezza Rice has never been shy about her love for football and has even expressed an interest in one day becoming commissioner of the NFL. So it’s no surprise that she’s been linked to former wide receiver and NFL director of football operations Gene Washington. The two met while Washington was an assistant athletic director at Stanford, where she was teaching (and even sat on the school’s search committee for a new football coach), and have stayed friends ever since. When Washington accompanied Rice for a 2007 state dinner with Queen Elizabeth II, rumors were rampant that the two were dating. Even though they’ve been spotted together since, both Rice and Washington insist that they’re just friends.
Washington, who retired from his NFL post last year, is not Rice’s only (rumored) football beau. She was engaged to Denver Broncos wide receiver Rick Upchurch in the 1970s, although she broke it off because she knew the relationship wouldn’t work. But of course, no potential Rice coupling could ever be as powerful as her unfortunately unsuccessful pairing with 30 Rock’s Jack Donaghy.