The reason men will always worry about this (and the same reason why women get annoyed when men are around attractive women) is because The Mating Game IS a Competition.
It IS.
Cultural/social controls offset the primal baseline but the primal baseline always remains.
When a man is not the best lover his woman has, she starts talking about & thinking about her past lovers. Those talks & those thoughts can easily lead to infidelity. When a man is the best he doesn't have to worry about his woman reflecting on past lovers. At the very least, the woman will only compare them to YOU saying how much they pale in comparison.
This Mating Game's ultimate purpose is about making sure your section of genetic code lives on. Mating is a form of maintaining immortality. YOU can't live forever but part of you does. The chance to be able to do this has limits so of course people will vie for those chances. Hence it becomes a competition.
When any lover male or female thinks—or worse—speaks out loud about past lovers, it's a bad sign. The relationship is in danger of wandering when that kind of stuff goes on. When you hear that kind of talk, it's an alert. Aspects of you may not be meshing enough with him/her to make him/her forget about the past. He/She may begin to try reliving the past & that's where the high school/college flame, ex-lover cheating starts.
People are more polygamous than monogamous as a rule. Society is really built upon a shaky bedrock which probably explains all the problems in the world historically & currently. We try to build society on the 'man-woman united for life' paradigm when it just doesn't really work long-term. The weakness of a newborn baby forces the temporary unity (if that). After the baby grows into a more independent child, it is all voluntary & conscious about the 2 sticking together. Why do you think there are such penalties in divorce? Why do child support payments exist? Why were there shotgun weddings in the past?
Why do you think every government in the world is so interested in regulating people's sex lives & push for marriage? Like China & its one child policy? Like Japan & Germany worrying about declining birthrates? Like the U.S.A. & this gay marriage thing? They need more fodder, more grunts for the workforces—civilian & military. Can't have that if the kids don't come up stable. They may die before reaching adulthood or be untrainable for the needs of the rulers who wish to live off the labors of the masses. China has too many people so they try to cut back & push for boys only since more girls mean more babies (1 man & 10 women can easily repopulate a depopulated island, 1 woman & 10 men cannot).
Of course there are a lot of other variables in the equation so just because someone thinks about past lovers doesn't necessarily mean they're about to cheat. But the spark is set once that thought crosses the mind. The counter-variables like his/her personality, his/her ability to stick to his/her stated moral code, pure opportunity, time, location can influence the final decision.
Contrary to what is often said, women DO see penis size as a factor in selecting a man. ALL women do. Each woman may rank this factor differently—higher or lower on the hierarchy of requirements—but that factor is there. That's why small-sized men as a rule run into many problems in the Mating Game. Men only compare sizes with each other out of the instinct to rank how attractive they can be to WOMEN. Same as how women size each other up to rank how attractive they can be to MEN.
If it wasn't important to woman as a rule, that kind of thing wouldn't exist and this very site wouldn't exist.
AND just because someone is not with a ex currently doesn't mean they have left that ex in their heart of hearts. Sex Quality is the main factor in a Lovers' Relationship. Unless each mates' sex drive is muted enough to be comfortable with only a Companion's Relationship, most people hate a relationship where the sex ain't right.
Bringing flowers, cards, & candy, remembering birthdays, getting along with the in-laws, taking out the trash, giving massages, asking her about her day & listening with a good ear...
...All that means nothing when the sex ain't right & most times women drop those relationships either outright or for all intents & purposes (meaning she stays on paper but her heart is somewhere else).
When a woman has top-notch sex with a so-called ex, she contemplates the option to go back to that ex for sex even within a supposed relationship. I never heard of a woman go back to a man who did the flowers, cards, candy, birthdays, in-laws thing.
So moral of story is: when a mate is talking about an ex, that mate is comparing you in their mind & testing if you are the right mate for them (according to their perception). While a woman may be "with you", she may not be WITH YOU in truth. The ex is only an ex because she wanted more than the sex from that ex. His deficiencies in the aspects of the Companions' Relationship led to the on-paper breakup. It's basically like she's taking a break & you're just fulfilling the Companion role she really wants from that ex who gave her the good sex. If you are able to surpass him, she may forget him & see you as her ideal mate. Then you have no challenger when it comes to passing on your seed, your genetic code to this woman you chose.
THAT'S why men worry about these things. It's not trivial, it's real. It's Nature.
John Lucas