1. If it's the first date. That's totally fine.
2. If it's the ninth date. That's just as fine.
3. If you're wearing "granny panties." They're coming off, so what's the difference. Sure, it's not "sexy" but cupcake wrappers don't look delicious. You're going to throw it in the garbage and eat the cupcake anyway.
4. That someone, at some point, is going to have to go fumbling awkwardly for a condom. Someone is going to have to pause the action to pull out a condom and wait for the nod of confirmation from other party that says, "Yeah, we're going to need that."
5. The fact that you even have a box of condoms. If you're the one grabbing the condom, don't worry about what kind of person having a box of condoms makes you look like. It's 2015. You look like someone who has safe sex.
6. If it's the best sex he's ever had, ever (EVER). No one wants their sex to be bad, but if it's the first time you two are fooling around, there are going to be hiccups (maybe literally). If you're into each other, you'll have plenty of other shots at making the sex better.
7. If you awkwardly elbow him trying to get your shirt off. Things happen. Just gloss over it and move on. Apologizing for 10 minutes kills the momentum.
8. Whether or not you shaved that morning. A little stubble never hurt anyone.
9. How the mood is set. The mood is "sex-having." That is fine. Don't worry about music and candles.
10. If you're wearing a padded bra. Don't feel like he's going to take off your bra and walk out screaming, "I've been duped!" Because he won't.
11. How many sex positions you run through. You don't need to prove anything by going through every single sex position you can think of. You can totally do that, but don't feel like you've got to hit every position on the Kama Sutra bingo card.
12. If it lasts "all night." Long enough that you both have an orgasm is sufficient. He might not be bragging to his friends the next day, "We totally had adequate sex until we both reached completion after several minutes," but you know, sex is a team effort.
13. If you need lube. Some people need a little boost to get started. There's nothing weird about it and you shouldn't go through discomfort instead of reaching for the lube real quick. Think of it like carbo-loading before a marathon.
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