Think of online dating as your new daily side hustle.
Ready to stack the online dating odds in your favor? A 2023 poll found that people between the ages of 43-58 had the most success on apps, with 72 percent embarking on a relationship with someone they met online. So if you’re newly single or finally feel ready to meet your person, now’s the time to finesse your dating profile.
“You have to be on the app every single day,” explains Amy Nobile, a New York-based dating coach whose clients are split evenly between millennials and the over-40 crowd. “It’s a true side hustle and it takes an hour-plus a day of swiping and talking just to result in one or two dates a week.”
And if you’re thinking, I miss the old way of dating, we’ve got a news flash. “Online dating is now just dating,” Clare O’Connor, Bumble’s head of editorial content says. “We remember a time where we could go into the grocery store and chit chat in line to meet people, or go into a favorite coffee shop and strike up a conversation,” says Nobile, who recently got engaged to someone she met on Bumble after a 20-year marriage. “It doesn’t work like that anymore.” Now, it’s all about mastering the art of online dating to find your next romantic partner.
But does online dating really work for people who are dating later in life? Is there actually any potential to meet a match? The answer is yes. But it’s a number game. “The reason my older clients don’t believe it works is that they dip their toe in for 10 seconds, take a look around, and then quit,” explains Nobile. “You really just have to practice at it. This is like flexing a new muscle or learning a new language.”
For millennials who grew up using technology, online dating feels a little more natural. “Millennials are so much more comfortable with technology transferring from online to offline. But for my clients over 40, they’re a little skeptical. This is sort of the first time they’ve really been vulnerable with technology in this way.” The best way to get over the initial virtual dating hump is to get clear with yourself on the type of partner or relationship you’re looking for.
For Nobile, it all starts with self-reflection. “You can only meet someone as deeply as you’ve met yourself,” she says. “I really believe that when you embark on this dating journey, you need to indulge in emotional self-care so that you can understand who you’re looking for from the inside out.” She even suggests bluntly stating what you’re looking for on your profile.
“Don’t be afraid to state, ‘I’m excited to press start on my second chapter.’ No matter what age you are, it’s important to state exactly what your goals are,” says Nobile. “Talking about being excited for this next chapter will really resonate with other people who are also excited about meeting their person.”
Below, we asked this dating guru for a step-by-step guide for older adults on how to date online — from the six types of pictures to use to the best conversation starters and how long you should spend each day swiping left and right.
Pick one dating app to download
For Nobile, there are three platforms to consider once you’re ready to flip the page on your next romantic chapter: Bumble, Hinge, and Match. “Bumble’s a really good app to start with because it has a very easy interface and women make the first move. It puts the power in women’s hands, which I really like,” she tells us. But only set up a profile on one app. “Don’t sign up for all three at once,” says Nobile. “Start with one.”
Grab a journal and do some self-reflecting
Before you start swiping, take a step back to figure out what you really want out of a partner. “We need to get really specific about what we want,” says Nobile. “Journaling through dating is really important. Start writing down who you’re looking for from a core values standpoint.”
For example, ask yourself questions like: What do I want? Who am I looking for? What are my core values?
Reflect your core values in your profile
The journaling exercise above will help inform the types of tidbits you want to include about yourself on your actual profile. “Come up with very specific examples that you can give,” says Nobile. “For instance, I have a client who has three sisters and she calls them her hype squad. They talk every day by FaceTime, so she mentions that in her profile,” says Nobile. “She’s attracting people who really relate to that. Like, Oh my gosh, no way! I’m really close with my family, too!”
The more examples you can provide that reflect what’s important to you, the more likely you are to find someone else that aligns with those values.
Be intentional (and honest) with the photos you use
The same rule applies to the photos you choose to include on your dating profile — they should reflect your personality (and they should be current photos). “A lot of times we are presenting an image of what we think our audience wants to see versus who we really are,” says Nobile. “It’s OK to be bending over backward laughing in one of your photos if you’re goofy and love to laugh.”
You typically need to include six photos (and Nobile cautions against selfies: “they’re a bit of a distorted view of who you are”). The first two should be headshots that “show the sparkle in your eye.” And no: they don’t have to be professionally shot. “Just have your best friend take them on portrait mode on an iPhone, outside, capturing that sparkle and smile.”
The next two should be full-length photos — from a wedding or an occasion that shows you a little more dressed up. The other can be one of your choice and then be sure to include one action shot. “If you love skiing or playing tennis, include a picture running on the court or bombing down the hill,” she says. Or if your dog is a big part of your life, include a photo of the two of you. And don’t use group photos — whether it’s family, friends, an ex, or your kids. “Anytime you’re making someone work to sort of squint to figure out who you are in this, it’s confusing.” And please, don’t use filters. “That’s a trend that’s on its way out.”
Keep the banter to a minimum
“If you’re bantering with someone on an app for two, three, four days, back and forth, and they’re not making a move to ask you out, they’re likely just a pen pal and that means they’re not aligned with you or they’re not ready to date,” says Nobile.
Always ask for the person’s last name before you give out your phone number
After some back and forth, it’s normal to want to start talking outside of the app. Nobile says to always ask for the person’s last name before you give your cell phone number and then do a quick Google search to make sure they’re a real person. “You can do it in a nice way, like, ‘Oh great! What’s your last name? I always ask.’” Be ready to give your last name, too.
But keep in mind: If the person gets defensive when you ask, exercise caution. “Something’s a little shady there. That’s not your person.”
Your first date should not be a real date
Your first date should always be a “mini screener date,” according to Nobile. These are 30 to 45-minute conversations (and it can be on FaceTime or the phone). “It’s coffee, juice, or an early drink — but you always ‘have something later’ so you have a hard out,” says Nobile. “We want to keep the stakes and expectations low. Mini screener dates keep things in a very safe space and for a short amount of time.”
Remember: Online dating is a numbers game
Think of online dating as your side hustle — and take it as seriously as you would any other job. “Put away whatever app you’re addicted to for the time being and plan on swiping and talking an hour a day,” says Nobile.
Your goal should be to have a minimum of two mini screener dates a week. “Give yourself two months and say, ‘Listen, I’m not going to judge myself. Statistically speaking, my soulmate probably won’t arrive immediately, so let’s give it time.” Another piece of advice: pretend you’re swiping for a best friend and find some amusement in the process.
Don’t take rejection personally
“We can’t take it so personally when someone rejects us,” says Nobile. “When someone shows us who they are right away, it’s getting them out of the way for the right person to arrive.”
Remember: no one really knows you and you don’t really know them, so it’s OK if you and/or the other person don’t feel a connection off the bat. “Pretend you’re doing this for your best friend when you’re swiping and talking. Be amused by it and remind yourself that it’s going to take some time.”
Ghosting and other quirky online dating habits can be puzzling to navigate for a generation that didn’t grow up dating online. “I spend a lot of time helping clients understand not to take it personally.”
Try to learn at least one new thing on every date you agree to
“When I was dating, I would say to myself, I’m going to learn one new thing from every single date I go on and I’m going to get really curious. I did that and I actually had a lot of fun” says Nobile. “You might surprise yourself. I’ve seen a lot of my clients end up dating fantastic people because they suspended their judgment and took that approach.”
Take an online dating timeout (when you need to)
If you go on three not-so-great dates, put yourself in an online dating timeout (but not for very long). “Give yourself two or three days and then put it back on your calendar starting on a Monday,” says Nobile. (Monday’s are the most popular days to join apps, she says).
But don’t give up entirely. “Strap in because it’s a roller coaster ride. And you just have to know that’s part of it.”
Adopt the three-four rule
Nobile says there are three things you must know by the end of your third date:
- Is there chemistry and a connection?
- Are our core values aligned?
- Is this person emotionally available and mature?
- Is the person on the same exact readiness scale as I am?
“There are questions you can ask that aren’t scary to sort of tease this out very early on,” says Nobile. “It’s essential to really roll up your sleeves and date with intention. This puts you in the driver’s seat, this empowers you, so that you’re not going on dates thinking, ‘I hope they choose me.’ It’s more like, ‘Hm, let’s see if we’re aligned.’ And guess what? If they’re not and they don’t call you back, it’s OK.” Just keep swiping.
Craving more dating advice? Check out Katie’s top five tips for dating after 40.
