The doctor is in—just in time for Valentine’s Day.

Dr. Jess O’Reilly is a Canadian sexologist and author renowned for her work in sexual health and relationship education. With over 20 years of experience in the industry and various published works—including The New Sex Bible (2014)—Dr. Jess advocates for healthy, fulfilling relationships and open communication about sexuality.

As a special treat, we’ve asked Dr. Jess to share her tips for modern dating, relationship faux pas, and advice on keeping that spark alive. Whether you’re in a relationship, single, or somewhere in between, this is Dating 101 for V-Day.

S: Can you give some advice to new couples for their first Valentine’s Day?

Dr. Jess: “The first Valentine’s Day with a new partner is an exciting time to start new traditions and conversations. Before the holiday arrives, make sure you’re on the same page in terms of how you’d like to celebrate—if at all. It’s important to discuss your needs and desires leading up to the event, this can help take the pressure off the first-time experience, and you can head into Valentine’s Day feeling confident and assured in your plans.”

“Opening communication around Valentine’s Day also offers an opportunity to have broader discussions around relationship dynamics, like boundaries, preferred ways of showing affection, and expectations for celebrations moving forward. Check in with each other about aspects of your relationship that may still be evolving given its newness. This tip also applies to couples in longer term relationships as, no matter how long you’ve been together, setting time to connect and reevaluate needs can be critical for continued romantic success.”

If I match on a dating app with someone on Valentine’s Day, what should I do?

“If you’d like to pursue a relationship with someone, no matter what form that might take, I always recommend being straightforward with your interest, and Valentine’s Day is no exception! Be unapologetic about what you want, and feel confident doing it because you’re not alone. In fact, Tinder’s 2024 Year in Swipe report revealed that Loud Looking (ditching vague signals in favor of specifically outlining needs and desires) is a top trend amongst daters. Valentine’s Day can offer an opportunity to try something bold and fun, perfect for making the first move.”

What is your worst Valentine’s Day story?

“I see this scenario play out all the time: one partner is waiting for the other to express love through a grand gesture while the other partner considers V-Day more of a greeting card holiday. Partner one is left inevitably disappointed, and partner two is overwhelmed by pressure. I find that couples who celebrate the relationship all year round feel less pressure around V-day and may not celebrate at all. Those whose emotional and relational needs are generally unmet can sometimes turn to special occasions with great expectations, whereas those who feel nurtured year-round are oftentimes less concerned with the holiday.”

If I’m in an open relationship, how should I split your time on Valentine’s Day?

“Each open relationship has its unique dynamic, so I’d recommend having a discussion with your partner[s] around their needs and expectations. Some may be very particular about wanting to celebrate Valentine’s Day, while others might view it as a day like any other, so checking in will give you the clarity you need to plan accordingly.  There are no universal rules when it comes to relationships regardless of whether they’re monogamous or ethically non-monogamous.”

What are your thoughts on proposing on Valentine’s Day?

“Engagements are highly personal, so there’s no hard and fast rule regarding whether someone should or shouldn’t propose on Valentine’s Day. If the day is of significance to you and your partner or you feel like the holiday’s focus on romance resonates with you, it’s as perfect a day as any other to propose! However, there shouldn’t be a heightened sense of pressure to propose on Valentine’s Day just because it’s a holiday.”

What is the proper etiquette for breaking up around Valentine’s Day?

“Breaking up can be a daunting task, further heightened if you plan on doing it during a holiday like Valentine’s Day. However, spending Valentine’s Day with a partner you no longer have romantic feelings for can be unfair and uncomfortable for all parties involved, so opting to end the relationship once you know it’s no longer a fit, even if this is around Valentine’s Day, can be the most optimal choice.”

“Much like a breakup during other times of the year, being open and gentle in your discussion with your partner is the best path. Be honest about your thinking, allow them to express their feelings, and thank them for the time you’ve had together. If possible, I’d recommend breaking up a few days or weeks before Valentine’s Day rather than the day of so your partner can plan accordingly and opt to spend that day with friends or family.”

What is your advice for reigniting the spark with your partner on Valentines day?

“Be playful in your daily interactions. You’re not a lightswitch, so you can’t go from talking about your taxes to seducing your lover into a moment of ecstasy. If you’re more playful in your daily interactions—and eroticize how you communicate—you’ll find that the spark lights more easily.”

What are some non-material ways to make my partner feel appreciated?

“Showing up for your partner in ways you know are important to them can often go further than giving a material gift. Do they despise folding the laundry but do it because you hate it equally as much? Consider taking on that task yourself for a day as a thank you. Small but impactful efforts like these can help signal your deep understanding of your partners’ efforts and needs. Rather than grand gestures on V-Day, consider 60-second favours every single day throughout the year.”

How do I leave a bad first date politely?

“While scenarios like this can feel awkward, having the clarity to recognize when a date isn’t going well or that you don’t feel a connection is beneficial for all parties in the long run. Rather than being ambiguous, the polite thing to do can simply be to thank them for their company and be upfront about not feeling a romantic connection. This level of open communication can allow your date to share how they’re feeling in return, and even if the relationship didn’t work out from a dating perspective, it creates a more authentic, person-to-person connection.”