Dear Anna,

My partner and I broke up in late April but we had a situationship over the summer. I’m a sophomore in college and I’m excited to get back out there. There’s one problem, I have no clue what I’m doing. I’ve only recently started to learn about sexual guilt and shame because I never focused too much on it while in my relationship. Now it feels like a balancing act between casual sex and dates and my emotional and sexual needs being fulfilled. Part of me wants to get off the apps because I’m not sure how cut out I am for this, but the stronger part of me wants to know what it’s like to date for the first time. (My ex was my only relationship.) I just want to be able to navigate this all a little easier. Thanks — Navigating Sex Awkwardness

Dear NSA,

First off, congratulations on stepping into a new chapter of your life with curiosity and a willingness to explore. Moving forward after a significant relationship can be both exhilarating and daunting, especially when it’s your first time diving into dating-app f—ery. It’s natural to feel like you’re walking a tightrope between wanting to experience casual dating and tending to your emotional and sexual well-being. The good news? There’s no “right” way to navigate this — you get to define your own path.

How do you do that? Let’s explore some options.

(First off, no more banging your ex. Give yourself a clean break with no lingering messiness.)

Then, give yourself permission to experiment. You’re entering uncharted territory, and it’s OK to feel unsure. Think of dating as a chance to learn about yourself — what you like, what you don’t, what feels good and what doesn’t. If casual dating or hookups appeal to you, allow yourself to explore that without judgment. On the other hand, if something doesn’t feel right, trust your instincts and pivot. You’re not obligated to stick to anyone else’s script.

Reflect on your values and boundaries. Take a moment to think about what you want from this phase of your life. Are you looking for lighthearted fun, deep connections, new experiences or something in between? Understanding your own needs and boundaries will make it easier to navigate the dating scene and say no to things that don’t align with what you want. For example, you might decide that while you’re open to casual relationships, you need to go very slowly and establish a lot of trust beforehand (and during).

Don’t ignore your emotions. Casual dating and hookups can be fun and fulfilling, but they also come with emotional complexities. It’s OK to catch feelings — or to feel disappointed when someone doesn’t reciprocate or want what you want. Try to approach these moments with self-compassion.

Take a break if you need it. If the apps or dating in general start to feel overwhelming or give you a sense of dread, it’s perfectly fine to take a breather. Sometimes, stepping back allows you to recalibrate and figure out what’s truly meaningful to you. Prioritize your well-being above all.

While you’re at it, now’s the time to start working through that lingering guilt and shame. We all have some sexual guilt and shame, often rooted in past experiences, crappy messages from family, religion or societal expectations, and these can very much impact our relationships and mess with our sex lives. Now’s the time to start unpacking and unlearning some of these harmful messages and traumas. If you can afford it, therapy can be a great space to explore and dismantle those feelings. If you can’t, there are lots of ways to do this work on your own, too. I highly recommend "Come as You Are" by Emily Nagoski and "Beyond Shame" by Matthias Roberts as starting points.

Embrace the learning curve. Dating isn’t about “getting it right” on the first try. You might ghost someone or get ghosted yourself. You might misinterpret signals or overthink a text. You might have underwhelming sex, like, a lot. (Then again, you might get your mind vagina-blown.) It’s all part of the process. Be patient with yourself as you trial-and-error your way through these experiences, and remember that every encounter — positive or negative — is teaching you something about who you are and what you want. Even if it’s just to “never again have sex with a dude who has a dollar sign tattooed on his genitals.” HYPOTHETICALLY.

This is your time to explore, and there’s no rush to figure it all out. Whether you decide to swipe on dating apps, meet people in person, or pause to focus on yourself, keep checking in with yourself and trust that you’re doing the best you can in this moment. Dating can feel messy and confusing, but it can also be instructive, and dare I say it, fun.

Wishing you clarity and confidence.

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