So you did it. You bought your first menstrual cup. Maybe you’ve been researching for weeks, or maybe you impulse-bought it after reading one too many glowing reviews. Either way, you’re probably staring at this little silicone thing thinking, “Okay… now what?”
I get it. That first time can feel intimidating. But here’s the good news: thousands of people figure this out every day, and you absolutely will too. Let’s walk through this together, step by step, so you feel confident and prepared when your next period arrives.
1. Before Anything Else: Sterilize Your Cup
Before you even think about using your new cup, you need to sterilize it. Every brand-new cup should be sanitized before its first use, even though it comes in sealed packaging.
How to sterilize:
- Boil it in water for 5-7 minutes (make sure it doesn’t touch the bottom of the pot—you can place it in a whisk to keep it floating)
- Use a steam sterilizer if you have one
- Follow your specific brand’s instructions
What about second-hand cups? Opinions are divided on this one. Because menstrual cups are made from medical-grade silicone and can be fully sterilized, many people consider buying or borrowing second-hand cups safe—especially when you’re testing different brands to find your Goldilocks fit. It’s a personal choice, and there’s no judgment either way.
2. Clean Hands Are Non-Negotiable
This one’s simple but critical: wash your hands every single time you touch your cup.
Before insertion. Before removal. Every. Single. Time.
This isn’t about being paranoid—it’s just basic hygiene that keeps you comfortable and reduces the risk of introducing bacteria where you don’t want it.
3. Folding Your Cup (There’s No “Right” Fold)
Here’s where things get hands-on (literally). To insert a menstrual cup, you need to fold it down to make it smaller. There are tons of different folding techniques out there—C-fold, punch-down fold, seven fold, origami fold—and honestly? There’s no single “right” way to do it.
Different folds work better for different people and different cups. Some make insertion easier, others help the cup pop open more reliably once it’s inside.
My advice: Start with the punch-down fold or C-fold (the most common), and if those don’t feel right, experiment with others.
And if you struggle at first? That’s completely normal. It takes practice to fold, hold, and insert all at once. Be patient with yourself.
4. Finding a Comfortable Insertion Position
Just like folding, the “best” position for insertion is whatever feels most comfortable for you.
Try different positions:
- Sitting on the toilet
- Squatting
- Standing with one leg raised (like on the edge of the tub or toilet seat)
- You can try even laying on the bed
The key is to relax. Tension makes everything harder (literally—your muscles will clench up). Take a deep breath, find a position that feels stable, and go slow.
5. Inserting the Cup & Checking the Seal
Once you’ve folded your cup and found your position, gently insert it into your vaginal canal. Aim it toward your tailbone, not straight up.
After insertion, the cup needs to fully open and create a seal against your vaginal walls. A proper seal = fewer leaks and more comfort.
How to check if it’s sealed:
- Run your finger around the base of the cup to feel if it’s fully expanded (no dents or folds)
- Give the base a gentle tug—if there’s resistance, the seal is working
- Some people give the base a little twist to help it open
If it doesn’t open right away, try pressing on the vaginal wall near the cup or bearing down slightly to give it room to expand.
6. Use Backup Protection at First (This Is Normal)
Here’s something nobody tells you enough: it’s totally okay to use a pad or period underwear as backup when you’re starting out.
You’re learning three things at once:
- How to insert correctly
- How to create a seal
- How much your cup can hold before it needs emptying
Small leaks during the learning phase are completely normal. Backup protection gives you peace of mind while you figure it all out. Once you’re confident, you can ditch the backup—but there’s zero shame in using it at first.
7. What to Do If the Stem Feels Uncomfortable
If the stem of your cup is poking out or irritating you, don’t panic. Most cups come with a stem that’s longer than many people need, and it’s totally okay to trim it.
Here’s the thing: trim slowly. Cut just a tiny bit at a time, then wear the cup for a while before trimming more. You can always cut more off, but you can’t put it back on.
And here’s the most important part: once your cup is properly fitted and inserted, you should not feel it at all. Not the stem, not the cup itself—nothing. If you’re constantly aware of it, something needs adjusting (position, size, or stem length).
8. How Long You Can Wear a Menstrual Cup
One of the best things about cups? You can wear them for up to 8-12 hours at a time.
That means you can put it in before work, go about your entire day, and empty it when you get home. Or wear it overnight without worry.
For beginners, though: Empty it more often at first—maybe every 4-6 hours—until you understand your flow and how quickly your cup fills up. Everyone’s different, and it takes a cycle or two to learn your rhythm.
And no, you don’t need to remove it to pee or poop. Your urethra and vagina are separate openings, and while bearing down during a bowel movement might shift the cup slightly, you can leave it in.
9. Removing the Cup Safely (No Pulling!)
Okay, this is important: do not just yank on the stem.
The stem is there to help you locate the cup, not to pull it out. If you tug on the stem without breaking the seal first, it’s going to feel uncomfortable (and possibly cause some suction weirdness).
Here’s how to remove it safely:
- Wash your hands
- Get into a comfortable position (sitting or squatting works well)
- Use the stem to reach the base of the cup
- Pinch or squeeze the base to break the seal
- Once the seal is broken, gently wiggle and pull the cup out
Go slow. There’s no rush. If the cup has moved up higher than expected, bear down (like you’re having a bowel movement) to bring it lower.
If you’re struggling or panicking: STOP.
This is so important I need you to hear it clearly: there is absolutely no way your menstrual cup can get lost inside you. Your vaginal canal is a closed space—your cervix is at the top, and the opening is way too small for a cup to fit through. The cup is in there, and it will come out.
I know it can feel scary if you can’t reach it easily or if your first attempt doesn’t go smoothly. But panicking will only make things harder because your muscles will tense up, making removal more difficult.
If removal feels impossible:
- Take a break. Seriously. Walk away for 30 minutes.
- Take a walk, have a glass of water, watch a funny video—anything to relax.
- Take a warm shower. The warm water helps relax your pelvic floor muscles and can make removal so much easier.
- Try again when you’re calm and your muscles are relaxed.
Tension is your biggest enemy here. The more relaxed your muscles are, the easier it will be to reach the cup and remove it. If you’re stressed and clenching, everything tightens up and makes the process harder than it needs to be.
And remember: you’re not the first person to struggle with removal on their first try. It happens. You’re learning a new skill, and that takes practice. Be patient and kind to yourself.
10. Managing Mess (Especially on Heavy Days)
Let’s be real: removal can get a little messy, especially on heavy flow days.
Here’s my personal trick: Keep a small piece of folded toilet paper in your other hand while you’re removing the cup. As soon as it’s out, you can use it to catch any drips or cover the cup while you carry it to the sink.
This has saved me from so many potential spills. It’s a small thing, but it makes a big difference when you’re dealing with a full cup.
11. Rinse, Reinsert, Repeat
Once your cup is out:
- Dump the contents into the toilet
- Rinse it with water (cold water first helps prevent staining, then warm to clean)
- Reinsert using the same folding and insertion steps
That’s it. Simple, practical, repeat as needed throughout your cycle.
At the end of your period, give it a more thorough wash with mild soap and sterilize it again before storing it in a breathable pouch (most cups come with one).
12. What’s Normal vs. What’s Not (Beginner Reassurance)
Let’s normalize the learning curve:
Normal:
- Needing a few cycles to get the hang of it
- Minor leaks while you’re figuring out the seal
- Trying more than one cup before finding your perfect fit
- Feeling awkward or clumsy during your first few tries
Not normal:
- Pain (a little pressure during insertion is okay, but sharp pain is not)
- Constant discomfort throughout the day
- Strong, uncomfortable pressure on your bladder or bowels
If something feels wrong—not just new or unfamiliar, but actually painful or distressing—listen to your body. It might be the wrong size, shape, or firmness for you.
13. How Long It Takes to “Get Good” at Using a Cup
Most people need 1-3 cycles to really get comfortable with their cup.
The first cycle is about figuring out the mechanics. The second cycle is about fine-tuning. By the third cycle, most people have their routine down.
This removes the pressure of thinking you should nail it perfectly on day one. You won’t. And that’s completely okay.
Give yourself grace. Give yourself time. The learning curve is absolutely worth it once it clicks.
14. A Quick Word About TSS
You’ve probably heard of Toxic Shock Syndrome (TSS) in relation to tampons. The good news is that TSS is extremely rare with menstrual cups—much rarer than with tampons.
That said, it’s still important to:
- Keep your hands and cup clean
- Don’t leave your cup in for longer than 12 hours
- If you ever experience sudden high fever, dizziness, vomiting, or rash while using your cup, remove it immediately and seek medical attention
TSS is serious, but with proper hygiene and responsible use, the risk is incredibly low.
Final Reassurance
Finding your perfect cup—and learning how to use it—takes time. There’s a reason people call it the “cup journey.” It’s not always smooth, and you might hit a few bumps along the way.
But here’s what I can tell you from experience: once it clicks, so many people never go back.
The freedom of not constantly running to the bathroom to change a tampon. The relief of sleeping through the night without leaks. The confidence of going swimming, hiking, or traveling on your period without stress. It’s all real, and it’s all worth the learning curve.
Trust your body. Be patient with yourself. And know that thousands of people have stood exactly where you are right now—a little nervous, a little unsure—and figured it out just fine.
You’ve got this.
Questions? Struggles? Wins? I’d love to hear how your cup journey is going—drop a comment below!