Heather Corinna replies:

Do you want to have a better sexual experience this time, as well as a relationship of real quality -- in which someone loves, likes and cares for you just as you ARE, not based on a persona -- with your new boyfriend?

If you do, then it's really important to be honest.

When we're dishonest with partners about things which are pretty critical, we make it difficult to impossible to have relationships, sexual or otherwise, of any real quality. It also, too, can feel pretty lousy to feel like a partner only likes or loves us based on some person we're not. In other words, if this person's -- or anyone's -- care is based in you not having an experience which you did have -- or in some idea of you that's not who you really are -- you're likely to feel like they don't really like or care for you for who you are. And that can feel really crummy. The very least you owe yourself when choosing a sexual partner is to choose one based on who you really are, 100%, and who accepts and likes you for who you are.

Too, it's important with any new partner that we're able to establish things to safeguard our sexual health and well-being. You've been sexually active before, for instance, so you should have started getting tests for STIs/STDs once a year now since then. Your new partner has also been sexually active before, so he too should be having those screenings. You'll want to talk about each of your status, and also will need to discuss all of this when you talk about using condoms and other sex safety issues. If you don't feel ready for those kinds of conversations -- which can be a little awkward, but which should otherwise not be a big deal -- then it's likely best to wait on any kind of partnered sex (not just intercourse) until you do. Sounds like you already had one bad sexual experience: you'll want to do what you can to have your sexual experiences from here on out be positive.

You'll also want to feel like it's no problem at all to tell a partner if things hurt right from the start and ask them to stop what they're doing if and when something doesn't feel good. If you know the way things went last time didn't feel good, you'll want to share that information with any new partner so that things really will feel better -- physically and emotionally -- the next time around.

Could he tell, physically, if you've had sex before? No, he really could not. But that also shouldn't be something that you have to keep a secret with someone who you're close enough to that you're having sex with them. It's also worth thinking about how you might feel if a partner of yours was dishonest with you about these issues. I think we all want partners who we know show us their whole selves and are honest with us about themselves, especially during sex, which is about intimacy as well as pleasure. We can't really experience the closeness of sex if there's a big, giant secret between us and our partner.

I get that there are some intense double standards for men and women when it comes to having had sex before: boys often get extra points for having had sex, and there's no shame put on them for it, and girls are often treated as if previous sexual experience is shameful. While we can only do so much to combat those ideas when it comes to our whole school or whole community or whole world, we DO get to choose who we have sex with, and we CAN only choose to have sex with people who do NOT think that way, and who value us just the same, no matter our experiences before them. Your boyfriend has also had sex before: if he applied a different standard to you than he does to himself, that wouldn't be at all fair, and the very least a partner owes us is that kind of fairness.

I don't know how close you are to having sex with this guy, but if you're close enough to it, I'd suggest you be honest with him, well BEFORE any kind of sex. You need to know before you have sex with someone that they like you, experiences and all, and will treat you with kindness and respect. You also shouldn't be fearful of a partner in any way. If he's not okay with this -- or you have a strong feeling that he will react to that information with anger or spite -- then he's probably not an okay person for you to be with. And if and when someone does not react well to you having had sex before, that's not a problem that's about you, that's a problem with THEM, and one THEY need to work out for themselves. Please know that.

Too, it sounds to me like it'd be a good idea for you to be sure that you're up to trying sex again with a new partner, so I'd suggest you take a look at our Sex Readiness Checklist here.

I'm seeing some possible spots on it where you might not be so ready, so do have a look.

Here are a few more additional links for you to help sort all of this out, and help assure that whenever your next sexual experience or partnership is, that it's a whole lot better for you than it was the last time.