Affairs are nothing new, with human beings engaging in “free love” for millennia. Not everyone fits into traditional romantic roles, which means that there’s always some flexibility regarding the concept of a “relationship,” and what comprises the boundaries of said coupling. Unfortunately, not everyone agrees on these finer points, which can often lead to “cheating,” having an affair, or being physical with another person, while still technically remaining in the dedicated confines of a traditional relationship.

It’s fairly obvious to assume that individuals looking to be, shall we say, “less than honest” with their romantic partners would need a way to do so in the safest & most secure ways possible. Without these sort of safeguards, the risk versus the reward would become unbearable for some. In some cases, the results could be as severe as lengthy legal battles, and the possible breakup of families. Sometimes you just need to resort to cheating, simple as that.

The Best Affair Dating Sites

This list was assembled to give those looking to move beyond their current situation the ability to do so without destroying either their lives or their reputations. Hopefully, one of the selections below leads you to what you’re looking for, satisfaction!


Ashley Madison may be the first affair website to have excited on the modern-day Internet, beginning originally back in 2001. Since then, they’ve remained largely the same, offering an array of privacy-based services for those looking to “have someone on the side.” In an effort to “grow with the times,” with the times, the site has expanded its offerings over the last few years to be inclusive to “non-binary folks, people who aren’t looking for an affair so much as an additional partner.

Something else that’s proven interesting about Ashley Madison is that they’ve eliminated the cost for women, in an attempt to even out the male to female ratio in their user base. Even with this, there’s still a larger amount of men on the site than women, although users tend to report success regardless, so the company must be doing at least a few things right.

In 2015, the website suffered a pretty large data breach, one that exposed a ton of personal information regarding their users, something that is doubly bad on a site built for affairs. However, instead of falling apart, Ashley Madison used this experience as a lesson to learn from, and have been incredibly dedicated to the perpetual improvement of their security features. If You’re looking to keep a secret in 2019, you could do a lot worse than this site.

—>  Ashley Madison review


Next on our list is a lesser-known company,, a fairly typical affair site that is “pay-to-play,” meaning that without a bit of money upfront for a trial membership, you won’t find very much to use here. If you do take the plunge, you’ll be browsing user profiles in under 5 minutes, thanks to the site’s simple & straightforward signup process.

One thing worth mentioning here is that Free2cheat claims its services to be marketed towards both men & women, but, while experiencing the site, it seems that the bulk of the marketing is directed towards men. You see an awful lot of mentions of “lonely housewives” & the like, without much in the way of “lonely husbands,” if you get my drift.

When looking into their traffic & metrics, the site seems to see a modest-yet-healthy amount of monthly browsing, which hopefully means that there’ll be a good amount of eyes on both your profile & outbound messages as you make your way through the site’s many features, including private messages & video chat.


Cheating Cougars is a bit more niche than the first two on this list, specializing in connecting older women with a taste for adventure to like-minded men that may be a bit younger. Word on the street is that their customer support is top-notch, and there’s plenty of reports from users online claiming success in meeting one or more partners. This is great, as the very first thing you want to see in a romantic connections site of any sort is a high success rate from past & current users.

Another positive to a site like this is that it’s never in question what these women are looking for, thanks to the site’s design. They’ve really nailed the affair market for “cougars,” with plenty of older women being paying & active members of the website.

The site’s look can throw some people off when first visiting, as it’s fairly generic & doesn’t offer much in the way of “flash.” With this concern in mind, we once again took a look at the site’s metrics. In May of this year, they made it over the 500,000-mark for monthly visitors, making for a pretty robust user rate.


This site is one that tries to offer its users a bunch of specialized features, meaning that they’re in essence increasing your chances of an affair connection while using the site. Their signup process is somewhat impressive, taking over 15 minutes to complete while asking a rigorous list of personal questions, meaning that there’ll be some precision to your searches right off the bat.

Something in particular that we enjoyed was the “Online Cupid” feature, which oddly enough has come under fire via reviews from jilted former members. These “cupids” are specialized users that are meant to stimulate search & conversation on the site. Bear in mind that these profiles, in particular, are meant to push the site’s “real” users to reach outside of their comfort zones and message more users, and aren’t actually themselves legitimate date possibilities. More details on these profiles can be found on the site’s Terms & Conditions.

The traffic on Lonely Affair is moderate, landing at roughly 200,000 page views per month. These tend to be centered in the continental United States, so those looking outside of the states may need to try one of the others on this list.


While this list certainly doesn’t contain every affair site out there, these should give anyone new to the game a head start in finding a website that fits their needs. Remember, loose lips sink ships, & secrets are best when kept. Now get out there and have some fun!