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The Perks—and Challenges—of Dating a Much Older Man

Anyone who’s been in a serious long-term relationship knows the journey isn’t without certain challenges, and when you’re dating an older man—we’re talking a decade or more—things can get even trickier.

I know this firsthand, as I’m 25 years old, and I’ve been dating an older guy nearly 15 years my senior for almost four years. While you figure out the math, let me be clear that I’ve met several other women in their early- to mid-20s who also prefer to date from a much older pool for various reasons.

And while cliche dictates that, sure, men are into it, there’s been some recent research done about why younger females often gravitate toward mature men. Evolutionary psychologists say that relationships like this often occur because while fertility lasts only from puberty to menopause in women, it starts at puberty and can extend long into midlife for lots of men. That means there’s a strategic advantage for women to snag an older gent—he’s had more time to accumulate resources and stability than his younger counterparts, which could make him a more viable partner and father.

Now, I’m not saying these are conscious reasons why I’m dating a man quite a bit older—there have been several moments when I’ve thought that going out with someone closer to my age would be much simpler. I even tried it when my boyfriend and I took a short break, and I found it was painstakingly difficult and more complicated than my experience dating an older guy.

You know what I’m taking about. The texting games (How long should I wait to text him back? Why isn’t he texting me back? Should I not be the first to text? It’s exhausting), the fear of commitment that plagues most twentysomethings, and the simple fact that most guys my age aren’t as emotionally mature as I am.

It can be tough when you and your older partner can’t share childhood commonalities (dude’s never read a Goosebumps book!?), but the benefits can certainly outweigh those little things. That said, there are not-so-little things that can cause friction too. Keeping in mind what I’ve learned from my own relationship and anecdotes I’ve picked up from women in similar situations, I’ve outlined the perks and challenges of dating an older man.

Jason Statham and Rosie Huntington-Whiteley: 20 years apart. (Photo: WENN.com)

He’s often financially stable. I get asked a lot of questions about my boyfriend’s finances (why else would I date someone much older, right? Ugh.). It’s not actually anybody’s business, but I can tell you that I’ve never dated anyone because of money. In general, there’s a stigma that a younger woman dates an older man because he’s more powerful and can essentially take care of her.

And while that may be true for some, a 2010 study by the University of Dundee in Scotland found that as women become more financially independent, their taste may skew toward older (and better-looking) men. What does that mean? As a woman becomes more confident in her own career and finances, she seeks a partner who matches that, which often is not a 25-year-old guy.

To be clear, my boyfriend isn’t rich, but he’s picked up one important habit over the years: investing. I have to admit it’s comforting to be in a serious relationship with someone who’s somewhat financially responsible (read: less impulsive). From what I’ve gathered, a man in his 20s is more likely to blow his cash on frivolous things, while men in their 30s and are likely to save money for the future or for experiences, like a romantic vacation (wink, wink).

No more texting games. “He texted me an hour after I texted him.” “What should I text him back?” Sound familiar? I can still remember the days when I’d utter those words and essentially have an anxiety attack every time my phone buzzed and it was a guy my own age I’d been casually seeing. When I first started dating my boyfriend, it threw me off when he didn’t text me, but—wait for it—called me instead.

And continued to call when he said he would and replied to messages fairly quickly. In general, dating games are rather boring to a guy who’s probably had his fair share. This alone is a reason why I refuse to go back into the dating pool with guys my own age.

Olivier Sarkozy and Mary-Kate Olsen: 17 years apart. (Photo: Getty Images)

His confidence gets major points. When I’m out, the guys I seem to attract are generally in their mid- to late-30s. Rarely do younger guys approach me. To find out why, I asked a straight twentysomething male friend, who pointed out that younger guys are simply intimidated. After all, going up to a total stranger in a bar and making an impression isn’t easy, and it takes a certain amount of confidence, which often comes with age.

Persistence also takes confidence—my boyfriend extended three invitations before I finally agreed to get coffee with him. As Aaliyah once said, “If at first you don’t succeed, dust yourself off and try again.” Older men know this.

He’s chock-full of knowledge. I won’t lie: It can be annoying at times dating someone who has “been there/done that,” but it can also be helpful when your partner can use his experiences to guide you. I can recall numerous situations—work issues, arguments with people—that my boyfriend was able to help me with based on his own mistakes and victories. Plus, when it comes to things like taxes, real estate, and life hacks that you pick up over time, an older guy can be a goldmine of useful information.

Jealousy takes a backseat. I dated a guy right before my boyfriend who was really … clingy. I’m the kind of girl who looks up to independent women, and I tend to put my girlfriends before dating. He just didn’t get that and wanted to be around every second. I don’t necessarily think that he wanted to hang exclusively with me all the time, but I think he felt insecure that I’d meet other guys when I went out with friends.

One thing I’m incredibly grateful for is not having to deal with jealousy in my current relationship. Sure, it occasionally happens, but my boyfriend understands that being in a codependent relationship leads to all sorts of trouble and that spending time apart sometimes is key.

Getting awkward questions (wait, how do you know each other?!). I find it difficult to explain to people how my relationship came to be. I’m often asked how we met—and not in a giddy kind of way (it’s more like concern). People are shocked when I respond “mutual friends.” How could a girl in her early 20s be friends with people in their late 30s? Well, I was (and still am) friends with a select crew of musicians and creatives in Los Angeles, and my boyfriend happened to be a part of that scene.

I get the impression that people outside my inner circle wonder if I’m lying and that maybe he picked me up at a hotel bar or something cliche like that. Other inquire whether I was purposely seeking an older man when I met him. (Spoiler alert: I wasn’t.)

Introducing him to your family won’t be easy. I was dead nervous to reveal my boyfriend’s age to my parents, so much so that I stalled introducing them for six months. If your family is fairly protective, especially your dad, it can be a pretty nerve-racking conversation. What helped me most was talking about how wonderful he is a lot leading up to their meet and asking my older sister to talk to them too.

You can’t expect him to drop his life to chase your dreams. Starting out in the fashion media industry isn’t an easy task, especially when you have zero connections. That’s where I was when I first met my boyfriend. I was a fresh-out-of-college aspiring digital fashion writer with no clue on how to break in. My boyfriend had been steadily working in his field for years, so it was hard to get him to understand things I felt I had to do in order to find success in my field.

Luckily, my boyfriend understands how important my career is to me, so there was never a question if I wanted to take chances like moving back and forth from Los Angeles to New York for amazing opportunities at dream companies or postponing planned dates because there was an event or story I needed to cover. But being with someone who has an established career and fully formed network hasn’t made it easy.

I’m aware that he will probably never move back to the East Coast, and I sometimes feel like I’m constantly straddling the line between doing everything I can to succeed in my career and maintaining my relationship.

Alec and Hilaria Baldwin: 26 years apart. (Photo: WENN)

Get used to the fact that he’s lived a whole life before you met. While I don’t have to deal with an ex-wife, stepkids, or any other ties to a former personal life—I don’t think I’d be able to handle that kind of responsibility yet—I know it can be a huge challenge for women who are in that situation. If your future with your boyfriend is important to you, these things might take a lot of talking and compromise to fit into your current life.

Your friends are very different. “You can bring [insert boyfriend’s name] if you want, but he might get bored.” I get that a lot. It doesn’t come from a negative place on my friends’ part, but they often don’t know how to react to my bringing someone who’s significantly older than them. I’ve done it, of course, and have witnessed some awkward exchanges between their twentysomething boyfriends and my own. It’s just something to get used to.

I won’t take him to a house party where Two Buck Chuck flows like water, but I will bring him along for some casual bar hopping. The same is true for me with his friends—I get bored sometimes hanging out with his friends’ girlfriends and wives. But it’s great to know the people that he considers his second family, to interact with friends that have witnessed him grow over the years, and to learn more about him through them.

As tricky as it can be at times to maintain your sanity in a relationship with someone older, if you love the guy as a person then it’s worth it. Not only has it taught me patience (which isn’t easy), but I’ve always been free to express myself and simply be me. He’s accepting.

Plus, it’s opened me up a whole network of people I wouldn’t have met and experiences I wouldn’t have otherwise had, which I feel has matured me a bit too. That’s not to say that I don’t act my age (trust me, my friends have the Snapchats to prove it), but I like that my relationship allows me to grow into the person I want to be.

Originally published October 2015. Updated April 2017.

18 Things I Learned About Being a Sugar Baby From Seeking Arrangement's Summit On Dating Rich Older Men

Devoted sex journalist that I am, when I heard thatВ SeekingArrangement.com was hosting its first-ever Sugar Baby Summit, offering an afternoon of seminars for both beginners and masters of the Sugar lifestyle, I eagerly accepted the invitation to attend. Who would pass up on a day of that followed by an evening of people-watching at an awkward dating mixer? But more on that later.

Sugaring, in case you're new to the sweet life, is a type of relationship/lifestyle in which a Sugar Baby (SB) "provides companionship in exchange for being pampered," while a Sugar Daddy (SD) "pampers Sugar Babies in return for companionship." "Pampering" is obviously a broad term, and can include explicitly negotiated financial compensation — like an allowance, tuition payments, or an investment into a Sugar Baby's business venture — or simply gifts, trips, and other treats. "Companionship" is an equally broad term, which can range from explicitly negotiated sexual contracts, to casual dating, to a monogamous relationship, to being a married Daddy's secondary partner.

"I feel like such a lady boss," veteran Sugar Baby ChelseaВ Ridenour tells the crowd during one seminar. "It's about looking for what you want, knowing your boundaries, being smart, going after what you want."

and coquettishness. Of course, these tactics have their place in any power dynamic. But only once you've explicitly discussed your needs, desires, and expectations, and established boundaries and consent. And these vital concepts in power play were completely glossed over at the Sugar Baby Summit in a misguided effort to make the Sugar lifestyle seem "accessible" and "mainstream."

For example, representatives from the website constantly obsessed over how the site was kept "PG." It was very clearly their intent to de-stigmatize Sugaring, and bring it into the light as a fun, exciting, sexy way to play, away from the shady taboos that are often associated with it.

I appreciate that SeekingArrangement.com is a business trying to turn a profit, and so the cogs of capitalism are going to be turning here. But saying that it's "kind of weird for a woman to be in the mommy role" certainly isn't empowering to the strong, financially independent women for whom the site also offers services. And saying that there's no market for LGBT events is patently false — the queer community has proven time and again that if you create accessible queer spaces, queers will come (operative word: accessible). The myth that there "isn't a market" for LGBT Sugaring can be dispelled with one visit to a "Gay Professionals" Happy Hour Mixer, and the same can be said for male Babies/Sugar Mamas by viewing of a single episode of Real Housewives of New York.

The summit revealed its latent anti-feminism again later with the sex-positivity (or negativity, as it were) issue of disclosing your kink identity on the site. SeekingArrangement.com seems like a natural place to go if you're a Fi-Dom (financial Dom/me, controlling the finances of your submissive) or a pay pig (the submissive moneybags who gets off on relinquishing power over their financial assets to a Fi-Dom). And several site reps admitted that these folks exist on the site. The CEO, Brandon Wade, even implied that it was easy, if you were a BDSM-oriented Sugar Baby, to search profiles and find Daddies who were too.

So, all you "weirdos" making folks "uncomfortable" with your legitimate desires: this might not be the most hospitable place for you.В I tried to ask what buzz words could get people scrubbed from the site, and was refused an answer:В "I can't tell you about the keywords, because if I did, then people would get around them by using other words, and we really don't want those kind of people on the site."

"Not that you aren't all beautiful without makeup," SeekingArrangement repВ Brook Urick gently told the Sugar Babies in attendance during her introduction. But it's mandatory.

"It screams high maintenance," said the hair and makeup expert, who goes simply by Phoenix. "They're afraid it's going to take you an hour to get ready."

Veteran Sugar Baby Chelsea told the crowd a cautionary tale of how she once got dumped for having makeup dregs in her sink when her Sugar Daddy came by to visit.

You're more likely to get cash out of your Sugar Daddy if you ask for money to help with specific costs: car payment, cell phone bill, student loan payments, etc. Successful business-type Daddies also respond well to requests for "an investment" into your business venture, be it your lifestyle blog or your web series. All of this is basically the classy way to be like, "give me x amount of dollars in exchange for my companionship now, please."

Sugaring is like any other form of freelance work — multiple streams of income is key. So what happens if you wind up with a possessive SD who doesn't want you seeing other guys? Expert SB Chelsea suggests taking this firm stance: "Look, if you're not gonna give me a big allowance and you're not gonna let me see other people, then I'm not gonna see you."

Chelsea recommends breaking the ice by asking "So why SeekingArrangements instead of a regular dating site?" It can provide a natural transition into talking about your needs and expectations, if the idea of a frank money talk feels forced and transactional to you.

So you want to go offline. If you're talking to a cute stranger and you want to know whether they have SD potential, try looking for expensive accessories (checking the quality of their watch was a specific tip), or bringing up "traveling." These can provide clues into their lifestyle and finances.

So you obviously have a moneyed human in your clutches while flirting in the field. How do you broach the subject of Sugaring? Chelsea suggests using the phrase "mutually beneficial dating." Ask them if they've heard of it, or if they have any interest in or experience with it. Perhaps open up about your experience/interest and see where things go.

A Sugar Daddy might be long-distance and ask you to travel to see him. Or, he might travel a lot himself and ask you to come with. Here are some safety tips to bear in mind when traveling for Sugar:

Forty percent of SeekingArrangement users are married Sugar Daddies, most of whom are acting with permission from their wives. Married SDs are "less clingy," says Chelsea, and they often give bigger allowances. They're also usually more relaxed about you having multiple partners.В

Don't call or text a married SD — their families might see those notifications on their phones; email is best when contacting a married SD. Also, don't hang out in their neighborhood on dates.

According to CEO Brandon Wade, "You don't care what other people think. You're into having fun. You have a lot to offer somebody else."

Then, commodify your knowledge of your needs. Your needs are your power. Express them to get what you want, or withhold the information to draw out mystery.В Says Brandon, "If you join the site for a Chanel bag, you're going to get used. The best way to a man's wallet is through his heart. I'd say no sex for the first month. Hold a lot of mystery. A-type players are successful and on the site for a challenge."

"I'm never going to have sex with you but I will let you think so for one more month," Chelsea recalls of her thought process dating one particular Daddy. So it is possible to commodify your flirtation, companionship, and attention, if you don't necessarily want to sleep with a potential Daddy.

There's a huge Sugar Baby community on Tumblr. Make friends, share experiences, learn new things, and, most importantly, publicly shame "Salt Daddies" — older men who date younger women but have "nothing to offer" them.

"I feel like a lot of guys resent me for being able to travel on my own," shared one independently wealthy Sugar Baby, who was mostly on the site to find guys with similar lifestyles.

A. Never introduce an SD to your kids, advises Vine star Danyelle Rose .

B. Don't bring up that you have kids until date five.

C. SDs who were raised by single mothers will allegedly have a lot more respect for you.

It's common for women to have regular boyfriends while they date Sugar Daddies, or while they have platonic Sugar Daddies. But Sugaring can ruin regular relationships, warns Brook.

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