Relax and take your time: Choose alone time when you can focus without distractions or interruptions. Perhaps after a warm bath when you are relaxed. If you are too nervous, the vaginal muscles will tighten, making it uncomfortable, if not impossible, for successful insertion.
Get Acquainted with yourself: It is always a good idea to know your own body. Take some time to locate the vaginal opening and even insert a finger to locate your cervix. It feels like the tip of your nose. Knowing where your cervix is will help you to position the cup properly and not insert it too high. If you have a high cervix, you may not be able to feel it with your fingers, which is totally normal!
Practice during your period: The vagina is more flexible and the blood works as a lubricant. Or . . .
Take a "dry run" before your period: You might be more comfortable practising before your period if you feel squeamish about touching blood. In this case, use water or water-based lubricant to make things easier.
Try different folds that accentuate the insertion point: Most use the typical C-fold. However, there are many ways to fold a Lunette. Check out the most common different folds that you can use with your period cup.
Proper insertion direction: Be aware that the direction of insertion needs to be aimed towards the small of your back — not straight up.
Be patient: Know that it may take several times before you are successful. If you begin without the expectation of perfect insertion, you are more likely to be relaxed and pleasantly surprised when success happens.
Assess the stem: Once inserted, you will need to decide whether or not to keep the stem. If it protrudes, it will be uncomfortable. In this case, you likely won't need the stem and can trim it shorter or off completely. However, if not, you may need it to assist with removal.