3 days ago
Why summer flings are better in your 40s — and how to have a healthy casual relationship, according to dating experts
"I have the confidence to be honest about what I want without fear of shame or rejection."
Feel like you've aged out of a summer fling? Think again. Sure, it might not be the casual romance you had in your 20s. But that doesn't mean a grown-up can't have a grown-up casual relationship for the summer.
This time around, you have enough wisdom and experience to set the pace, boundaries and expectations with healthy communication — as well as a healthy dose of fun. So what makes a summer fling actually work when you're in your 40s or older? We asked relationship and intimacy experts to break it down.
Set your boundaries and expectations
There's nothing wrong with wanting a casual summer fling. It's how you go about it that makes the difference. Kelsey Grant, a Vancouver-based love and relationship coach, says it starts with clarity.
"Healthy elements come down to being incredibly clear on what you actually want," she says. "The only way I've ever found a casual relationship to work is when there is clarity around (it), what the agreements are and the duration. ... Uncommunicated expectations are at the root of a lot of relational disappointments, especially in more casual relational containers."
Dr. Jessica O'Reilly, a sex and relationships expert at We-Vibe, agrees that it's up to you to define what feels right: "Define what's healthy for you. It might be something casual or a connection that blossoms into something longer term," she says, adding that "you want to treat your 'fling' with care and respect regardless of whether it's just a summer fling or a long-term connection."
As a widow, mother and founder of dating apps like Chapter 2 and Sober Love, Nicky Wake knows how important that kind of clarity can be. When she met a handsome divorcé on a solo cruise, she made her intentions clear: She wanted a steamy, no-strings-attached holiday romance — and that's exactly what she got.
"It was clear we both had really enjoyed the fling and were keen to keep in touch, but we are both practical and realistic," says Wake. "We had an honest conversation and mutually agreed that, given neither of us were looking for anything committed or serious, anything long-term would be impractical."
Their connection, which started with bold moves and cheeky banter, has continued through sexy weekend meetups — all without the pressure to define it beyond what feels good in the moment.
Communication is key
Communication is everything — especially if you want a summer fling that doesn't lead to confusion or disappointment. Stating your needs upfront can feel intimidating, but it's essential.
"We tend to avoid uncomfortable conversations and, in doing so, we often create uncomfortable situations," says O'Reilly. "If you want something, say so. Be honest from the onset to reduce confusion in the weeks and months to come."
If you're looking for a short-term connection, O'Reilly recommends being clear from the start: "Let them know, and consider being specific about your availability. Maybe you want to see them once a week, or perhaps you prefer not to text during the week while you're working or your kids are home. The more context you provide, the fewer details they have to fill in with their imagination."
That approach worked well for Wake. "I shared with him that I identify as polyamorous and wouldn't be in a position to commit to anything monogamous," she says. "He was comfortable with that. We agreed to keep in touch and see each other when we can. We enjoy the time we have together, don't worry about the future and just stay in the moment."
Wake currently lives in the U.K. but travels to the U.S. every couple of months for business. She always tries to meet up with Troy, who lives in Denver, Colo. She also says that her age has played a part in helping her see what she wants.
"Being in my 50s has given me the confidence, experience and wisdom of 30 years of dating," she says. "I can clearly communicate what I'm looking for and what I expect in relationships. I have the confidence to be honest about what I want without fear of shame or rejection."
Cultivating confidence
If confidence is something you're still trying to build, Grant suggests leading with your desire and communicating with an open mind.
And assuming the person you're into is already interested in a summer fling, Grant suggests being direct. "Say something like, 'I really want to have a fun summer fling with you," she says. "What a summer fling means to me or looks like to me is ____. For it to be a yes for me, this is what I need: ____.' Then ask them, 'What do you need for this to feel fun, respectful and like a yes for you?'"
Don't forget your pleasure
Summer flings are supposed to be fun and sexy. In turn, don't forget to lean into your desire and pleasure.
"Earlier seasons of sex tend to be more performative — it's about looking good and avoiding looking bad," Grant says. "By 40, you just don't give a s—t about the same things. You know yourself better. As a woman, you are hitting your sexual prime. So not only will your sex drive likely be higher, but you'll also feel more at home in your body and more in tune with what you actually like. ... As a woman in my 40s, I'm also not willing to do something that doesn't feel right or aligned."
If you need help feeling more confident about expressing your sexual desires or preferences, O'Reilly says self-pleasure can help. "Get to know your own body. Take your time to explore and experiment. The more comfortable you are with your body, the more likely you'll be comfortable when someone new joins in," she explains.
Sexual health doesn't have an age limit
If you're entering a casual relationship, talking about sexual health and protection is an important step to take, regardless of age.
"If you can't talk about sexual health, STI screenings, protection methods and pregnancy, you're not ready to have sex yet," Grant says.
Since these are vulnerable conversations, Grant advises speaking first. "Don't put them on the spot and expect honesty. Lead with honesty and courage, and you're more likely to get the same in return," she says. "A simple, 'My last screening was on ___. The results of that were ___. The protection methods I am comfortable with are ___. In the event of an unplanned pregnancy, what feels right for me is ___,' goes a long way."
Be realistic, but also stay in the moment
They're called summer flings for a reason — they're not supposed to last forever. But still, you're often putting your feelings on the line.
"Sex is intimate. We are going to bond and develop a connection," says Grant. "If feelings start to develop, you bring it up the second it becomes a thing."
Grant suggests language like: "I'm noticing I'm starting to develop deeper feelings here. Given this is a fling, I want to bring it up for us to talk about. The feelings I'm feeling are ____. What I'm noticing it's changing about what I want is ___. Curious to know how that leaves you feeling?"
Grant adds that you also have to know your limits: "If developing feelings means you no longer want to proceed, then it's time for a conversation about ending or completing the agreement. If the relationship feels more open and fluid, you might just need to name the shift and keep going. There is no one-size-fits-all playbook."
From her own experience, Wake echoes this realistic-yet-romantic approach. "Once the vacation romance is over, you have to remember 'it is what it is.' It's a holiday romance, so recognize and acknowledge that. Enjoy every second, but do not expect to be able to replicate that emotional intense high in the real world," she says. "Sometimes it is so much better to have fun over a summer romance than being ghosted by texts as life painfully returns to normal."
