But for few rare exceptions, Chess, as it relates to Love, Romance or Sex, involves the inter-relationship between the two genders. Since Chess is often thought of as a male-oriented game, it's the inclusion of females that sparks the fire. How men have reacted to this inclusion or how they have depicted it in art and literature is the measure.

   Until the end of the 19th century women, for the most part, were expected to limit themselves to the artistic or domestic sides of chess, leaving the competitive side to the men. This attitude gave rise to the literary fantasy of powerful women players, a fantasy that might have evolved into the preoccupation with the physical attributes of today's women players.   

  
     This fantasy first occurred in the early days of chess (Shatranj) and was expressed in the famous compilation of stories, 1001 Arabian Nights. The story tells of Tawaddud, the slave-girl who excels in many areas including chess:
 

O Tawaddud, there is one thing left of that for which thou didst engage, namely, chess.” And he sent for experts of chess and cards and trictrac. The chess-player sat down before her, and they set the pieces, and he moved and she moved; but, every move he made she speedily countered,—And Shahrazad perceived the dawn of day and ceased saying her permitted say.      When it was the Four Hundred and Sixty-first Night, She said, It hath reached me, O auspicious King, that when the damsel was playing chess with the expert in presence of the Commander of the Faithful, Harun al-Rashid, whatever move he made was speedily countered by her, till she beat him and he found himself checkmated. Quoth he, “I did but lead thee on, that thou mightest think thyself skilful: but set up again, and thou shalt see.” So they placed the pieces a second time, when he said in himself, “Open thine eyes or she will beat thee.” And he fell to moving no piece, save after calculation, and ceased not to play, till she said, “Thy King is dead!—Checkmate.” When he saw this he was confounded at her quickness and understanding; but she laughed and said, “O professor, I will make a wager with thee on this third game. I will give thee the queen and the right-hand castle and the left-hand knight; if thou beat me, take my clothes, and if I beat thee, I will take thy clothes.” Replied he, “I agree to this;” and they replaced the pieces, she removing queen, castle and knight.449 Then said she, “Move, O master.” So he moved, saying to himself, “I cannot but beat her, with such odds,” and planned a combination; but, behold, she moved on, little by little, till she made one of her pawns450 a queen and pushing up to him pawns and other pieces, to take off his attention, set one in his way and tempted him to take it. Accordingly, he took it and she said to him, “The measure is meted and the loads equally balanced.451 Eat till thou are over-full; naught shall be thy ruin, O son of Adam, save thy greed. Knowest thou not that I did but tempt thee, that I might finesse thee? See: this is check-mate!” adding, “So doff off thy clothes.” Quoth he, “Leave me my bag-trousers, so Allah repay thee;” and he swore by Allah that he would contend with none, so long as Tawaddud abode in the realm of Baghdad. Then he stripped off his clothes and gave them to her and went away. (translation by Richard Burton)

One of the earliest Arabic references to woman chess player was found in letters between Nicephorus I, the Emperor of Byzantium, and Caliph Harun-ar-Rashid of Bagdad where Harun-ar-Rashid mentions that he just bought a slave-girl who was particularly noted for her skill at chess. Harold James Ruthven Murray, in his "The History of Chess," mentions the same Caliph Harun-ar-Rashid who, after losing three consecutive games to a slave-girl, offered her a reward of her own chosing. As her reward she chose the release of a prisoner, apparently her lover, named Al-Mamun.

Dilaram was the favorite wife of Grand Vizier's harem. Her husband, Murwadi, had been playing chess for high stakes and losing badly. He had lost his entire fortune, his possessions and finally all his wives except for Dilaram. He finally used her as stakes for his last chance to gain back some of his losses. But his game looked bad, especially since his opponent would mate him on the next move. Dilaram was, of course, watching the game of her fate closely. She was a much better player than her husband, and actually much better than his adversary. She looked at the position on the board and saw how her husband could win. Since she wasn't allowed to advise him, she clothed her instructions by shouting, "Sacrifice your two rooks, but don't sacrifice me!" He husband considered her words carefully and found the winning moves.

The story above accompanied a position (called a Mansuba) entitled "Dilaram’s mate" and was first recorded by Firdewsi at-Tahihal in his book on chess in the 15th century. It's suspected that the story and problem were first given  in the 10th century book, Kitab Ash-Shatranj by the legendary Abu-Bakr Muhammad ben Yahya as-Suli.
This site shows the position in Chess terms
This site shows Dilaram's mate in Shatranj terms
This site shows Dilaram's mate in Shatranj terms (scroll down until you reach Dilaram's Mansubat to play though it)

The fantasy of the powerful woman chess player culminated in the creation of Caïssa, the goddess of Chess. Caïssa was invented by Sir William Jones, the hyper-polyglot mathematician in his1763 Latin poem of the same name. In the poem Ares, the God of War, pursued Caïssa, a dryad, with little success. The God of Sport advised Ares to create a game for her to win her over. That game was Chess.

Later writers were less interested in the fantasy and more intent on metaphors and symbols and the game of Love.

            .

 

CHECKMATE.
Two games I played with lovely Bess,
A game of love and a game of chess.
In chess I was driven to the wall;
In the game of love she gave me all;
And when my men fell all ill-fated,'
'Twas not my king alone was mated.
                                 -Yale Record.

From a review of T. S. Eliot's The Wasteland:

                                            TS ELIOT’S “THE WASTE LAND”
           Sex in High and Low Level of Society
The second section of the poem is A Game of Chess. The title is borrowed from Middleton’s play Women Beware Women. A Game of Chess is played to distract the attention of an old woman, while her daughter-in-law is seduced by a lustful duke. The knock upon the door will be a signal that the love affair should be brought to an end.

Even Shakespeare (1564-1616) incorporated a well known, though minor, chess scene in The Tempest.

The Tempest: Act Five, Scene One  (Ferdinand and Miranda)
The entrance of the Cell opens, and discovers Ferdinand and Miranda playing at chess.
Miranda: Sweet lord, you play me false.
Ferdinand: No, my dearest love, I would not for the world.
Miranda: Yes, for a score of kingdoms you should wrangle, And I would call it fair play

Miranda and Ferdinand are lovers whose fathers are sworn enemies. Their love, represented in a devious game of chess in the final scene,  restores harmony between the two families

            Ferdinand and Miranda playing chess (1871)
                      Lucy Madox Brown (1843-1894)

A more recent interpretation of Shakespeare used Chess as a metaphor for Love. Here is an internet posting advertising a CAMBRIDGE UNIVERSITY'S EDINBURGH 2003 SHOW

LOVE'S LABOUR'S LOST AS YOU'VE NEVER SEEN IT BEFORE!
Want to play a game?....

Cambridge University Ariel Society is proud to present their Edinburgh Fringe 2003 Show ‘Love’s Labour’s Lost’. Taken from the Shakespearean script, this production seeks to fully foreground Shakespeare's already self-conscious dramaturgy, and provide an insight into his most enigmatic play.

Set around the concept of a chess game, ‘Love’s Labour’s Lost’ becomes a game of love. The battle of the sexes, the elaborate moves and countermoves of the men and women, and the assumption wrongly made by the women that the courtship is just sport are all heightened by the chessboard setting. Chess appears throughout the script, along with countless other images of games, playing, winning... and losing.

The late 15th century Valencian poem, Schacs d’Amor (Eschacs d’amor) by Francesc de Castellví, Bernat Fenollar, and Narcís de Vinyoles, pits Mars, the god of War, against Venus, the goddess of Love, in a game of Chess and a game of Love. Mars controls the red pieces with Love as his battle cry while Venus' battle cry is Glory with the green army. They both assign virtues or attributes to each of their pieces (e.g. Venus' pawn, Courtesy; her queen, Beauty; her king, Honor; her knight, Contempt and Mars' white bishop, Thoughts; his queen Willpower; his rook, Desire). Mercury acts as the arbitrator. Eventually, her Contempt fails to defend her Honor and his Thoughts overpower her Gaze and Willpower supported by Desire mate her.  Metaphor heaven.

Mars and Venus at Chess by Alessandro Varotari (1588-1648)

Chaucer (1343-1400) took a rather clever approach. Instead of lovers (or simply a man and woman) playing a symbolic game of love, the man plays a game (in a dream) against Fortune and losses his "Queen," his "bliss."[which appears similar to stories of a man playing the devil for his soul in a symbolic game of Good versus Evil in the game of Life]. This story is related in one of his earliest works, Book of the Duchess:

"'What has she done, trow you? By our Lord, I will tell you. She played at chess with me; with her divers false moves she stole upon me and took my queen. And when I saw my queen gone, alas! I could play no longer, but said, "Farewell, sweet, in truth, and farewell all that ever there is!" Therewith Fortune said, "Check! " and then "Checkmate!" in the middle of the board, with a roving pawn, alas! She was more skillful at play than Attalus - so he was named-, who first made the game of the chess. But would God I
had once or twice known and understood the problems that the Greek Pythagoras knew thereby I had played the better at chess, and the better had guarded my queen. And yet to what end? Truly I hold that wish not worth a straw. It had been never the better for me. For Fortune knows so many a fetch that there be but few who can beguile her. And eke for another cause she is the less to blame; before God) I myself would have done likewise, had I been in her place; she ought the more to be excused. For this I say, had I been God and could have had my will, when she captured my queen, I should have made the same move; for, so God save my soul, I dare well swear she took the best!

'But I have lost my bliss through that move; alas that I was born! For evermore, I truly believe, in spite of my will, my pleasure is wholly at an end; but yet what is to be done? By our Lord, it is to die quickly! In spite of all I give not up the thought, but live and die therein. There is no planet in the firmament, or element in the air or earth, that gives me not the gift of weeping, when I am alone. For when I consider well, and bethink me how nothing is owing me in mine account with sorrow; and how there remains no gladness which may gladden me in my distress, and how I have lost content and have no pleasance left; then I may say, naught remains at all.
And when all this falls into my mind, alas! then I am overwhelmed! For what is done is not still to come. I have more sorrow than Tantalus.'

When I heard him tell this tale so piteously as I have told you, scarce could I abide longer, it did my heart so much grief. 'Ah, good sir!' quoth I, 'Say not so. Have some pity on that nature which makes you a living man! Remember Socrates; for he cared not three straws for aught that Fortune could do.'

'No,' quoth he, 'I cannot do thus.'

'Why so, good sir?' quoth I. 'Perdy! say not so, for in sooth, though you had lost the twelve pieces, if you murdered yourself for sorrow, you should be condemned in this case as justly as Medea was, who slew her children for Jason (and Phyllis also hanged herself for Demophon, alackaday! because he broke his appointed time to come to her). Another frenzied lover was Dido, queen of Carthage, who slew herself because Aeneas was false. Ah! what a fool she was! And Echo died because Narcissus would not love
her; and even so has many another wrought folly. And Samson, who slew himself by means of a pillar, died because of Delilah. But there is none alive on earth who would make this woe for a queen at chess!'"

From The Modern Reader's Chaucer, ed. John S. P. Tatlock and Percy MacKaye (New York: Free Press, 1912).

Even before Chaucer, the Celtic mythology contained a story called the the Wooing of Étaín. In this story, which is rather complex, Étaín's former husband challenges her current husband to a series of chess games for stakes. Her former husband, Midir, loses on purpose to her current husband, Eochad until the final game in which a single kiss from Étaín is the stake. A good summary can be found here.

In reality Chess was played by women in the Middle Ages, but their participation was usually limited to playing their husbands or betrothed. In that sense depictions of women playing at chess with men often symbolized the relationship between the man and the woman.

Chess was taught to well-to-do young ladies as part of their education

According to Eileen Powers' (1889-1940  Professor of Economic History at the London School of Economics in 1931, Professor of Economic History at the University of Cambridge in 1940. She founded the Economic History Review in 1927) published lecture series, Medieval Women :

EDUCATION OF UPPER CLASS WOMEN
Many girls were educated by being sent to nunneries.
The following applied to the education given the girls in the nunnery.
Young girls were taught to:
· Read and write
· Tell stories, read romances and judge the merits of poetry.
· Learn of Ladies fashion and appropriate dress.
· Polish their manners and learn to speak properly.
· Hawking
· Play chess
· Singing lessons

In the above 1405-10 picture by the Masters of the Dirc van Delf found in the manuscript,
Tafel van den Kersten Ghelove, a husband and wife play a game of chess together.

But this connection between Chess and Love, according to Hans Scholten in his article for the exhibition catalogue of Queens move: Women and chess through the ages, eventually was corrupted into something less pure. He presented two examples:

The painting on the right is The Chess Players by Cornelius de Man (1621-1706).  Scholten expounded:

De Jongh notes a few cliché-like details which in genre painting are frequently applied in the erotic context (the cat looking up to the woman, the string instrument hanging from the panelling, and the bellows in front of the fireplace). These details, added to the meaningful look of the woman, the embarrassed man, the informal clothing
and the open box bed, guarantee that the message will come across.

Likewise, Christopher Brown, in 'Tot Lering en Vermaak at Amsterdam" (Burlington Magazine, Vol. 119, No. 886 Jan. 1977) wrote: "The legend beneath the Kornelius de Man from Budapest which shows a man and a woman playing chess - "The woman plays with the man, now on the board, after in bed?" - may seem crude, but it does convey the sense of  the picture

The drawing by Gerard van Honthorst (1590 - 1656) on the left shows a man playing chess with prostitutes. He's reaching for his purse while cupid is blindfolding his eyes.

Scholten wrote:

‘The man whose eyes are blindfolded by a flying cupid reaches for his purse. Blinded by love all he can do is to make a silly move. He has already lost his game with the whores. The concept of Love should not be conceived as being too romantic, because of the purse and the sensual meaning of the cupid.

This poem, published 1557, speaks for itself:

To the Lady that Scorned Her Lover
by Henry Howard, Earl of Surrey (1517 - 1547)

Although I had a check,
To give the mate is hard ;
For I have found a neck,
To keep my men in guard.
And you that hardy are,
To give so great assay
Unto a man of war,
To drive his men away ;

I rede you take good heed,
And mark this foolish verse ;
For I will so provide,
That I will have your ferse. (queen)
And when your ferse is had,
And all your war is done ;
Then shall yourself be glad
To end that you begun.

For if by chance I win
Your person in the field ;
Too late then you come in
Yourself to me to yield.
For I will use my power,
As captain full of might ;
And such I will devour,
As use to shew me spite.

And for because you gave
Me check in such degree ;
This vantage, lo ! I have,
Now check, and guard to thee.
Defend it if thou may ;
Stand stiff in thine estate :
For sure I will assay,
If I can give thee mate.

 

In the 18th century, there seems to have been a less strict idea of a woman's conduct concerning chess and they're conception of the women and chess during the Middle Ages seems at odds with current thought:

from The Sports and Pastimes of the People of England
         (by Joseph Strutt. London: J. White, 1801)

DANCING AND CHESS PLAY.--Dancing was certainly an ancient and favourite pastime with the women of this country: the  maidens even in a state of servitude claimed, as it were by established privilege, the license to indulge themselves in this exercise on holidays and public festivals; when it was usually performed in the presence of their masters and mistresses.

In the middle ages, dice, chess, and afterwards tables, and cards, with other sedentary games of chance and skill, were reckoned among the female amusements; and the ladies also frequently joined with the men in such pastimes, as we find it expressly declared in the metrical romance of Ipomydom. The passage alluded to runs thus:

"When they had dyned, as I you saye,
Lordes and ladyes yede to to playe;
Some to tables, and some to chesse,
With other gamys more or lesse."

In another poem, by Gower, a lover asks his mistress, when she is tired of "dancing and caroling," if she was willing to "play at chesse, or on the dyes to cast a chaunce."
Forrest, speaking in praise of Catharine of Arragon, first wife of Henry VIII., says, that when she was young,

"With stoole and with needyl she was not to seeke,
And other practiseings for ladyes meete;
To pastyme at tables, tick tack or gleeke,
Cardis and dyce"--etc.