A Rebounder's Guide to Casual Dating

Tips and tricks from seasoned veterans, professional experts, and InStyle readers.

Two people looking at each other, seated at a cafe
Photo: Sergio Marcos/Adobe Stock

After a breakup, casual dating can be exhausting and discouraging if you’re not prepared. Re-downloading dating apps can feel like being launched into space. However, dating also has its upside. It has the potential to be a lot of fun and a great way to meet new people. Plus, it may help you to figure out what you want or where you want to go romantically.

While there’s no one right way to get back out there, I spent the last year doing field research, getting it down to a science. Then, I asked relationship experts and InStyle readers for their best advice when it comes to casual dating. Be it a rebound season or just time for someone new, I wholeheartedly can endorse these tips.

1. Get to know yourself first.

Smiling person seated across from someone at a restaurant

Gurki Basra, most recognized from that episode of Dating Around on Netflix, gave some sage advice about how to prepare before you take to the apps and get out in the field. “My biggest piece of advice for anyone that’s taken a break from dating and entering back into the scene or just got out of a relationship would be to get to know yourself really well before dating,” she says. “You change and evolve as you get older and what your needs and wants were when you were younger may be very different. It’s important you know who you are and what you want out of life.”

She even suggests a break from social media to get in touch with your intuition, rather than comparing yourself to anything you see on Instagram. Then, when you do meet someone you're interested in, “you’re in tune with yourself enough to be able to proceed in the relationship with maturity and awareness.”

2. Create a list of what you want.

Before getting on the apps, make a list of what you want from your ideal partner. Be specific! And yes, that includes the physical details. I started with a list and every now and then revisited the list to make sure I wasn’t settling or making compromises on what I wanted for myself when it came to things like communication and affection. This will be the blueprint for how to identify potential love connections and what to advocate for in a relationship.

David*, 29, New York

“Communication and honesty from day one.”

— David*, 29, New York

3. Honestly communicate your expectations and boundaries.

Don’t assume that the person you’re seeing shares the same expectations as you. Make sure the person you’re sharing a meal with knows that you’re looking to keep things casual and that you’re on the same page. (If keeping things casual is what you truly want!) This will set the expectations and ensure that you won’t be wasting someone’s time or leading them on a road to nowhere.

Gina*, 29, Philadelphia

“Respect each other and communicate your intentions”

— Gina*, 29, Philadelphia

4. Cast a wide net.

Remember, this is about trying new things, figuring out what you want in a future partner, and getting to know more about yourself. Keeping your options open will provide you with different scenarios, attachment styles, and provide you with a crash course in fielding red flags. Date around and dare yourself to say ‘yes’ to new experiences. One piece of advice that might save you from some heartbreak? “Don’t get attached too quickly!” says Sarah*, 28, Brooklyn. On the flip side, don't feel bad about cutting things off if you aren't feeling it, rather than trying to force a connection that just isn't there.

Marc* 30, New York

“It’s okay to tell the other person you’re not interested”

— Marc* 30, New York

5. Try to actually have fun.

This should go without saying, but if you’re miserable and not enjoying the process at least a little bit, you’re probably doing things all wrong. “Dating should be fun. When you are having fun, the person you are with is more likely to be having fun too,” says Cher Gopman, a professional dating coach behind NYC Wingwoman.

Sarah*, 28, New York

“Peace out as soon as you get bad vibes or see red flags. No excuses for them!”

— Sarah*, 28, New York

6. Talk about testing!

Make sure you’re setting clear boundaries and getting on the same page about sex. Get comfortable with talking about sex by practicing expressing consent and getting serious about discussing STDs. Talking contraceptives is a golden rule for keeping things casual and seeing multiple partners.

Selena*, 28, New York

“Don’t f**k on the first date if you feel pressured! Only do it if you’re 1000% into it.”

— Selena*, 28, New York

7. Date with intention.

Learning how to identify red flags is invaluable. Dating can give you a better understanding of what you’re looking for in a long-term partner and a great crash course in how to set your standards high and avoid dead ends. So on that note, revisit your ideals list. It might be time for revisions every now and then as you learn more about what you want (and definitely don’t want). Looking back, I've been surprised by how my desires have evolved and how closely they've mirrored my next partner.

Heather*, 22, Denver

“It’s about figuring out if YOU like them, not trying to prove you’re a worthy date.”

— Heather*, 22, Denver

8. Be present.

“There are three main points to hit when you first meet someone you are interested in. Smile, ask questions, and relate,” Gopman says. That also means when someone is talking, actively listen to them. “Try to tune out the inner monologue in your head so that you can gauge if you are enjoying who you’re speaking with. Sometimes, we’re so worried about what to say next or if someone likes us that we don’t even pay attention to if we like them," Basra says.

Joanna*, 33, Jersey City

“Lately I’ve been telling myself ‘don’t overthink things,’ ‘be cool, not drama’. ‘Que sera, sera.’”

— Joanna*, 33, Jersey City

9. Check in with yourself.

This time is about you. Pay attention to how you’re feeling and if it stops being fun, take a break for self-care and reflection. “Dating can be as much about understanding yourself as it is about finding the right partner. New people, challenging conversations and novel experiences can be doors to better understanding our own values, needs, and desires,” says Jessica January Behr, Psy.D., a licensed psychologist and couples therapist.

Asking yourself some tough questions can also help you do this. "Asking things like, 'How do you choose to present yourself? What qualities of a date intrigue you? Which repels you? What are the core values you present or are drawn to? Where might these values come from?' can help turn even an awful date into a fruitful learning experience," Behr says.

10. Consider therapy.

My therapist has truly been the most helpful source when it comes to dating. I can’t recommend therapy often enough as an essential tool in learning about how to identify your attachment style, your needs, and how to communicate in romantic relationships. “Therapy can be a place where you more deeply explore your inner self, building confidence in your innermost needs and your ability to express them clearly to others,” recommends Behr. Learning what you want, learning how to ask for it, and how to exit situations that don’t serve you are the key tools you need to start dating casually.

And in my opinion, if there’s only one tip that you take away, it's this: Never settle!

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