13 Best Free Younger Woman, Older Man Dating Sites of 2019

Senior Dating

13 Best Free Younger Woman, Older Man Dating Sites of 2019

Amber Brooks Amber Brooks
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Every time I meet a guy I’m interested in, I’m quick to text my friends a gleeful, exclamation-point-filled message about him, and they’ll tell me about their crushes in return. We trade heart-eyed emojis and encouraging words often without even seeing the mystery man or woman in question.

So, it surprised me when a friend texted me “I think I have a crush, but please don’t judge me.” She’d fallen for a man nearly 20 years older than her, and she talked about his good qualities in an apologetic, emoji-less way. Because of the age difference, she didn’t feel excited to share news about her love interest, but she couldn’t deny the chemistry between her and this older man.

Sometimes the love bug hits you, and you can’t help pining after someone older or younger than you. Age-gap romances have actually become more common nowadays thanks to online dating. The following dating sites support younger women who want to meet older men (and vice versa) and pursue their desires without restraint.

★★★★★
4.9/5.0

Relationships: Friends, Dates, and Relationships

Match System: Browse by zip, age, appearance, more

Our Experts Say: “Match.com has more "over 50" members any other dating site, and it has a simple matching process that is responsible for millions of romantic connections...” Full Review »

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We recommend Match as the overall best dating site for singles of all ages and backgrounds. Since 1995, this dating site has attracted relationship-minded singles. Most Match members are more interested in deep compatibility than superficial attraction, and that’s why they’ve sought an alternative to the swipe-crazed dating apps out there.

Match has stood the test of time because its algorithm pinpoints important compatibility factors and introduces singles based on their date criteria. No swiping necessary.

★★★★
4.4/5.0

Relationships: Dates and Relationships

Match System: Search by profiles by zip and more

Our Experts Say: “OurTime is just for men and women who are 50 or older, and it's one of the most popular dating sites in this niche because of its size...” Full Review »

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OurTime has taken a page from Match’s playbook by putting shared interests first and foremost, but it has tailored its services to meet the needs of a more mature crowd. OurTime is a premium senior-friendly dating site designed to help singles over 50 meet.

That doesn’t mean it keeps younger singles from joining the network, however. Anyone interested in meeting older gents can create a free account on OurTime and start browsing by age and location.

★★★★★
4.5/5.0

Relationships: Friendship, Casual Dates, Serious Relationships

Match System: Search by age, location, height, education, ethnicity, and religion

Our Experts Say: “SilverSingles caters to relationship-minded singles over 50 with simple, safe, and effective online dating tools...” Full Review »

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SilverSingles is another dating site geared toward the senior singles of the world. Unlike OurTime, SilverSingles only allows individuals over 50 to sign up. That means age-gap romances formed here are usually between 50-somethings and 70-somethings. But, hey, young is in the eye of the beholder.

Singles over 50 can feel young again by going out with an older single who appreciates their vitality. SilverSingles uses a streamlined matchmaking process to help men and women find the person who’s right for them.

★★★★
3.5/5.0

Relationships: Hookups, Chats

Match System: Search by encounter, location, and more

Our Experts Say: “BeNaughty is a premier hookup app where you can feel comfortable expressing your desires. Plus, it's free to join, browse, and flirt...” Full Review »

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Not all young women and older men are dating for keeps. Some just want to have their fun while they can and enjoy a short-term romance. BeNaughty was designed to help these daters get what they want with no muss and no fuss.

BeNaughty is a hookup site where singles don’t have to be ashamed of their naughty desires. The adult-friendly platform makes forbidden fruit easily accessible so sexy singles can find someone who appeals to them.

★★★★
3.5/5.0

Relationships: Hookups Only

Match System: Search by location, interest, more

Our Experts Say: “Make no mistake: this site isn't about making friends, it's about short-term "hookups" and affairs only. Note that a basic account costs $14.95/month, but it's well worth it if casual sex is your goal...”

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Adult Friend Finder encourages singles to unleash their wild sides and discover flirtatious dates within a few clicks. This hookup site doesn’t require singles to make a big commitment to join the network. All they need to provide is a username, email address, and a few basic details.

AFF chat rooms are notoriously raunchy, so be prepared to move at a fast pace and engage in many sexually charged conversations here.

★★★
3.4/5.0

Relationships: Hookups Only

Match System: Search by location, interest, more

Our Experts Say: “A hookup site specializing in casual encounters, secret affairs, live chats, and member videos, FriendFinder-X skips the awkward "dating" stage of a relationship and fast-forwards straight to the sex...”

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Since 1996, FriendFinderX has featured the dating personals of singles and couples looking for straight-up sex. This dating site gives people the space to pursue their desires and live out their fantasies. Whether you’re dreaming of a sugar relationship, a threesome, or a one-night stand, you can enjoy a variety of sexual experiences thanks to FriendFinderX’s network. To use the words from the site, “You’re never too busy for a great sex life.”

7. SeekingArrangement

SeekingArrangement empowers smart, beautiful, and successful singles to seek a relationship on their terms. The sugar dating site facilitates mutually beneficial relationships. Its members know their worth and want a romantic partner who shares similar interests and goals.

Screenshot of the SeekingArrangement homepage

SeekingArrangement doesn’t make singles feel bad for dating younger or older people.

Women vastly outnumber men on SeekingArrangement — there are four sugar babies for every sugar daddy — and they compete for wealthy dates who will treat them right. It’s free for women to sign up and chat, but men must invest in the site to reap its benefits. SeekingArrangement currently has over 10 million members in 139 countries, and it is still growing worldwide.

8. WhatsYourPrice

Since 2010, WhatsYourPrice.com has made a splash in the online dating scene by allowing single men to bid on dates with single women. The sugar dating site’s goal is to facilitate as many first dates as possible and keep singles from wasting time chatting online. The site cuts right to the chase and requires its members to invest in each other if they want to make a connection.

Over 2 million singles have joined What’s Your Price, which has seen over 4.8 million bids on first dates. Men have bid anywhere from $125 to $400 for the chance to actually meet someone they find attractive.

As a spokesperson for What’s Your Price said, “Our overall goal is to grow the footprint of the site and to take the stigma away from sugar dating and add more legitimacy to the lifestyle.”

9. SugarDaddy.com

Known as “the king of all sugar daddy dating sites,” SugarDaddy.com is the perfect dating ground for younger women and older men. The site was named after sugar daddies, but it also welcomes sugar mommas and their admirers. New users can identify themselves as a sugar daddy, a female sugar baby, a sugar momma, a male sugar baby, a gay sugar daddy, or a married person seeking an affair.

Screenshot of SugarDaddy.com

SugarDaddy.com offers sugar daters a free trial so they can see what’s out there.

New users can set age or location parameters when creating a profile, and SugarDaddy will cater its matches and search results accordingly. The website also has advanced search features to allow singles to find someone who’s exactly their type. SugarDaddy.com doesn’t have a companion app, but it is mobile-friendly, so you can still access the network from your smartphone or tablet.

10. RichMeetBeautiful

Sigurd Vedal founded RichMeetBeautiful to enrich the lives of singles who have a lot going for them, but are missing a partner to share the wealth. RichMeetBeautiful uses smart matchmaking to introduce millionaires to beautiful, model-quality women. The dating site excels at pairing wealth and beauty, but it doesn’t support sugar dating.

RMB members are smart, successful, and attractive individuals in their own right, and they don’t need or want financial support. These singles are after an elite dating experience with someone who is on their level.

“Your life is yours and yours alone. So are your choices and decisions,” said Sigurd. “Don’t let anyone to stray you from your path. Here at RichMeetBeautiful, we are committed to our mission, which is to allow you to take the liberty of living on your own terms.”

11. SugarDaddyMeet

SugarDaddyMeet has over 1.5 active members, and over 1,000 singles join the sugar dating site every day, so it must be doing something right. You can use the traditional search filters to find profiles in your town, or you can join the discussion forums to get acquainted with the people online. SugarDaddyMeet members are happy to share stories about their experiences sugar dating and give advice to newcomers seeking a date. It’s a supportive atmosphere where sugar daddies and sugar babies can learn the ropes.

Screenshot of SugarDaddyMeet.com

The SugarDaddyMeet dating site has dozens of success stories to its name.

SugarDaddyMeet publishes its success stories to show the positive experiences and fruitful relationships that can come from online dating. Some members have made friends, found relationships, gotten married, and even started families thanks to this sugar dating site.

SugarDaddyMeet has the search tools to help young women find dateworthy older men online, and it’s worth checking out the network if you’re interested in sugar dating. You can read our full review of SugarDaddyMeet here.

12. SugarDaddyCatch

SugarDaddyCatch has over 750,000 active members, and over 70% are young women who identify as sugar babies. The dating site allows women to pursue high-powered men willing to pamper them. Privacy is a top priority on SugarDaddyCatch, so the site doesn’t ask for personal details and doesn’t require users to use their full names while online.

Jessica L. said she was skeptical at first when she heard about SugarDaddyCatch, but she joined to see what it was all about. She was immediately impressed by how many messages she received in her inbox, and the first man she replied to ended up being her dream guy. “He has been just wonderful, and I think we have a good connection,” she said.

13. SugarDaddie.com

Since its launch in 2002, SugarDaddie.com has promoted sugar dating and made a name for itself as a premium dating resource. Over 5 million singles have joined the dating site in search of a mutually beneficial relationship. SugarDaddie.com’s testimonials speak to its success at pairing up high-caliber singles.

Screenshot of SugarDaddie.com

SugarDaddie.com is another resource for younger women seeking older men in the dating scene.

“I just want to say that I think that this is a very classy website,” said Ashlie in a SugarDaddie.com review. “I respect the fact that you screen profiles and photographs. It not only ensures the individual’s safety, but it maintains your high standards.”

Non-members can browse SugarDaddie.com for free, though they are limited to seeing only 100 profiles. If you want to use the site’s search tools and contact a sugar daddy or sugar baby, you’ll have to create an account.

How Do I Attract a Younger Woman? How Do I Attract an Older Man?

Attracting a date who’s younger than you can be tricky because you’re competing against singles in their 20s and 30s. It’s important not to emulate these youngsters but to make yourself stand out by being more mature, experienced, and charming than they could ever be.

“What I want from my sugar daddy is more than just money,” said a sugar baby in an anonymous post. “I want someone [who’ll] be there for me. A listener, a shoulder, and, most importantly, a friend.”

As a sugar baby, the attraction game is much more straightforward. These hot women can usually catch a man’s eye easily enough, but then they have to make sure they have enough substance to hold his attention.

Why Do Younger Women Date Older Men and Vice Versa?

Sugar dating is pretty common in certain circles. All those dating sites we listed wouldn’t exist if younger women and older men weren’t drawn together for some reason. What is that reason? It differs for everyone. Some women are attracted to maturity because they’re tired of playing childish games with their dates. Some men think younger women will be easier to please than their exes were.

Some people cynically say sugar babies are only interested in the bottom line when they date older men, but many are also interested in the man attached to the wallet. They want a sugar daddy who will shower them with compliments as well as gifts. They want a man to treat them like gold and help them reach their goals.

Photo of a sugar daddy and two sugar babies

Sugar dating can be a great confidence booster for men and women who know their worth.

Sugar daddies, too, are often interested in a date who is as beautiful on the inside as she is on the outside. They’re attracted to young women who have a taste for the finer things in life and are willing to travel the world on a moment’s notice. Sugar daddies relish the opportunity to be a mentor for young women and open the door to new experiences and adventures.

“As a sugar daddy, you are in the honeymoon stage most of the time,” said an anonymous sugar daddy. “You get treated well, you get lots of romantic evenings, and you are seen as a savior of the women in distress and the facilitator of her better lifestyle.”

It works out well for both individuals — that’s why it’s called a mutually beneficial relationship.

What are the Pros and Cons of Younger Women Dating Older Men?

Like everything, dating older men has its ups and downs. It’s not all champagne and trips to Paris, but it can be exactly what you need if you’re willing to make it work. We’ll start with the good news. Here are the pros of dating an older gentleman:

  • He’s financially stable enough to spoil you.
  • He’s experienced in the ways of romance.
  • He’ll appreciate your youth and beauty.
  • He can take the lead and show you a great time.

Older men know what they want and who they are, and that’s appealing to a lot of young women. A mature relationship means you don’t have to play games or be coy asking for what you want. You can skip the drama and just have fun together. Of course, dating someone older has a few cons to balance out the pros.

  • He may not share your taste in movies, music, or food.
  • Starting a family together may be difficult.
  • His health may deteriorate as he gets older.

You may not always see eye to eye with someone significantly older than you. His life experiences are different, so he may not understand why you geek out over Harry Potter or maintain a vegetarian or vegan diet. He may not want to start a family with you because he already has children or doesn’t want to settle down. And, finally, an obvious downside is that he probably won’t live as long as you will, and you may find yourself nursing an old man while you’re still in your prime.

Are There Any Statistics About Successful Younger Women, Older Men Relationships?

SugarBabiesOnline assessed over 20,000 sugar dating profiles across multiple dating platforms to discover trends in the dating scene. This in-depth research yielded insights into the ages, professions, and relationship goals of sugar daddies and sugar babies everywhere.

Screenshot from SeekingArrangement.com

According to SeekingArrangement, 2.7 million students have become sugar babies to bolster their finances.

The study found that 87% of sugar daters are primarily interested in short-term relationships. The survey also showed that about one-third of sugar babies are students.

According to a recent SeekingArangement study, about 37% of college students would be willing to try sugar dating, while 7.4% of students have actually been in a sugar relationship previously.

SeekingArrangement ranked the colleges attended by its members in order of popularity and declared Georgia State University to be the top sugar baby academy of 2019. My alma mater, the University of Florida, came in at the #5 spot. You can see the concentration of SeekingArrangement members in your area by using the site’s Sugar Dating U.S. Hot Spots tool.

What Movies and Books Feature Younger Women Dating Older Men?

Many movies play out the fantasy of a wealthy older man taking an attractive younger woman under his wing. “Pretty Woman” is probably the most iconic movie with this theme. Richard Gere is 18 years older than Julia Roberts, but that didn’t stop the then-40-year-old stud from getting the girl.

A "Casablanca" movie poster

Released in 1942, “Casablanca” is a classic romance story involving an older man and younger woman.

In “Casablanca,” Humphrey Bogart was 43 when he successfully wooed the 27-year-old Ingrid Bergman, whom he affectionately called “kid.”

Bradley Cooper has paired up with younger ladies in many blockbusters, including “Silver Linings Playbook,” “A Star is Born,” and “He’s Just Not That Into You.” He has played the love interest for Jennifer Lawrence (16 years younger than him), Lady Gaga (12 years younger than him), and Scarlett Johansson (10 years younger than him).

Plus, in real life, Bradley is in a relationship with Irina Shayk, who is 11 years younger than him.

Other movies featuring age-gap relationships include “Breakfast at Tiffany’s,” “An Education,” and “Black Swan.” If you’re looking for a book about sugar dating, you should check out the “Fifty Shades of Grey” series.

Younger Women Can Attract Older Men With Ease Online

Age-gap romances can receive criticism from people outside the relationship, but the heart wants what it wants. Sometimes the most compatible partners can be decades older or younger than one another.

If you’re a young woman interested in an older man, you shouldn’t have to feel ashamed of your desires. My friend hesitated to follow her heart when she met a charming, witty, and kind man in his 40s, and she could have missed out on something great because she feared what people would say.

Online dating empowers singles to boldly pursue their dream dates and build loving relationships. No matter how old you are, you can use sugar dating sites to expand your horizons and meet successful, attractive, and interesting singles who are looking for someone like you.