10 Best Intergenerational Dating Sites

Men's Dating

9 Best Intergenerational Dating Sites (Feb. 2024)

C. Price

Written by: C. Price

C. Price

C. Price is part of DatingAdvice.com's content team. She writes advice articles, how-to guides, and studies — all relating to dating, relationships, love, sex, and more.

Edited by: Lillian Castro

Lillian Castro

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It’s the 21st century, and more people are starting to embrace age-gap dating. You can’t put a number on love, and no one believes that more than our 10 Best Intergenerational Dating Sites!


Bragging Rights: Highest amount of singles of any dating site

When it comes down to it, Match is the best dating site and app around, especially for mature men and women looking for younger singles — and vice versa. Not only does Match have 13.5 million users on the site every month, but it also has a free 7-day trial, which allows a new user to fully test it out before jumping in. Match welcomes singles of all ages, and it has smart filters to ensure compatible people can find one another.

Monthly Users: 13.5 million

Age Meet


Bragging Rights: do what makes you happy

“If life is offering you a chance to be with a person you like, then grab it while you can,” is the motto of Age Meet, where users get together through targeted searches and online dating site recommendations. Instant messaging, emails and flirts are available all hours of the day. Users create a dating profile as detailed as they like and can share interests and photos with potential dates.

Social Clout: 3,889+ likes, 551+ followers

URL: http://www.agemeet.com/

Age Match


Bragging Rights: brings a friendly approach to age gap dating

Age Match connects daters across an impressive global membership. Users find one another through basic searches of interests, locations and age perimeters. They can even link their blog to the site or have the site host one for them. Flirting through “winks” is encouraged and protective features are provided. An active forum is also available for advice and friendly chat.

Social Clout: 175+ likes, 15+ followers

URL: http://www.agematch.com/

Age Single


Bragging Rights: age is no longer important

For 11 years, Age Single has successfully helped connect people who celebrate age gap dating. With a client base that extends to CEOs, professional athletes, doctors, lawyers, models and cheerleaders, the site aims to match you with someone real, serious and of solid quality. Dating advice, safety tips and true success stories are shared by users and authors alike.

Social Clout: 556+ followers, 22+ likes

URL: http://www.agesingle.com/

Bragging Rights: a safe haven and open community

Ron and Gayle have been married since 1986, with a 15-year difference between them. They created the site as a place for those seeking a May-December romance and offer a full collection of “tips, tricks and tools to help you create a successful relationship in any season!” Pooling together their personal and professional experience, Ron and Gayle bring a unique vantage point.

Social Clout: 174+ likes, 59+ followers

URL: http://maydecembersecrets.com/

Bragging Rights: recapture your youth and strike up a relationship

Ageless Dating is designed for men and women who don’t rule out a relationship with someone significantly older or younger than themselves. Specializing in making meaningful age gap connections, the site encourages users to “leave behind the embarrassment and annoyance of ‘everything to everyone’ dating sites” and offers a searchable database for finding that special someone.

URL: http://www.agelessdating.com/

Bragging Rights: avoid sifting through thousands of people

“Age is just a number” is the founding belief behind this online dating site, which caters to those seeking intergenerational relationships. Those May-December romances are embraced with a considerable archive of dating tips specifically geared to age disparity. Member profiles are also carefully screened to ensure 100 percent age gap dating.

URL: http://www.itsjustanumber.com/

Bragging Rights: breaks beyond the stereotype of the “daddy”

Buck Up, Princess offers dating advice specifically for singles in the gay community, authored from the perspective of an older man interested in younger men. With a funny and proud approach, the site offers a fuller view in a community where May-December pairings are quite common. Topics like “There’s No Fool Like an Old Fool” detail the joys and hardships that often accompany love.

URL: http://toppist01.blogspot.com/

Bragging Rights: funny and serious

This friendly and conversational blog provides articles and stories written by both sides of a loving May-September relationship. Posts get right at the heart of the matter, with titles including “Cheat? Are You Freaking Kidding Me?” and “It’s Forever Now.” Sex, laughs, viagra and more are celebrated, thanks to an archive stretching back to 2009.

URL: http://datingtheolderman.blogspot.com/

Bragging Rights: honest and thoughtful

Date Rich Men gets right to the point with content specifically crafted around finding a financially secure partner. Topics include the risks to a relationship involving age gaps and an exploration of the many reasons some women prefer the older alternative. Articles are not just drawn around the very young, but instead the full community of May-December lovers.

URL: http://date-rich-men.blogspot.com/

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