
Welcome to 5C Shades of Grey, a sex advice column serving the Claremont Colleges since 2025. We’re two self-proclaimed advice experts at TSL taking on the great honor of writing a Valentine’s Day edition of the paper’s beloved but irregularly published sex column.
How do I ask a guy to be my sneaky link if I know he likes me?
So let’s get this straight — you know this guy likes you and you want to hook up with him, but you haven’t told him? Just tell him. Stop playing games with this poor man’s heart and get your freak on.
I feel like I’m never going to lose my virginity. How do I become more confident in myself and put myself out there to meet people? I keep on waiting for the right moment, but I’m becoming impatient and at this point just want to lose it.
Everyone makes such a big deal about having sex for the first time. So, going into sex with the mindset that it’s nothing more than something to check might actually hold you back. And honestly, even having prior experience still won’t make it “the right moment” because sex is so much more than just getting it done — it’s about having fun! We wholeheartedly recommend waiting until you feel ready, not just because you want to get it over with.
And if there is one thing we won’t bash, it’s dating apps. Sure, it can feel daunting to get on there. You might think, “Oh, but then everyone on there will know I’m looking!” Baby, they’re on there too. It’s a level playing field. But if online is not your style, try extracurriculars! The Mudd BDSM Club may no longer be extant, but having a common interest other than taking your clothes off may serve you well for post-coital chit-chat.
Is there a universal way of having sex as LGBTQIA+ people? Why does everyone expect and naturalize certain practices as the “norm”?
There simply is no one way to have sex. Straights, this is for you too. Even hetero sex is so often socially intertwined with procreation and gender norms that many straight people really do only know one way to have sex.
Queer sex is beautiful. Partly because it inherently runs against the norm and mainly because it’s pleasure, it’s expression, it’s exploration, it’s safety with another person and it’s fun. Still, it’s easy for queer people to fall into reproducing traditional gender roles or trying too hard to completely avoid them.
And as a result, you and your partner (or partners) (shout out to our poly and open relationship readers) don’t end up getting what you need. Above everything, the most important thing is being comfortable communicating to your partner(s) what you like and what you’re curious about.
Remember that sex is not stagnant. It’s a part of your being and who you were yesterday, who you are today and who you will be tomorrow very well may be different people, let alone years from now.
“There simply is no one way to have sex.”
I was talking to someone but the night before we were gonna meet they canceled and haven’t messaged me since. This is the second time things have sorta just fizzled out, I don’t know what I’m doing wrong. I don’t have much experience and am wondering how most relationships progress.
First of all, it sounds like you aren’t doing anything wrong. If there’s one thing about dating in college, it’s that this is going to happen. Over and over again. And again. Sometimes, you need to get through a few flops to find something good.
Trust us, we’ve seen this to be true. From getting bitten by a CMCer to going on a dismal dinner date at Frary, we’ve had our fair share of “fizzling.”
A close friend recently went through a similar situation to what you’re describing — after a series of unsuccessful courtships through three years of college, they finally landed a baddie and they have undeniable chemistry!
To address the next part of your question on the progression of situationships to relationships, it’s a much less complicated line to dance. While there may be ways to alter your strategy to find a mate, keeping up the facade of appealing to what you think they want probably will not work in your favor. Some people here are not ready for a relationship, and it takes two to tango.
Faking early on (in more ways than one …) will only lead to struggles down the line, so make sure you both want the same thing. Be clear with your expectations and be okay with them not being met. This doesn’t mean you’re finding your soulmate, but communicating early can save you a lot of trouble in the end.
But also, do try to be open and find the balance between being flexible and listening to yourself on what you want. There is an irony to being okay with not being in a relationship which may make it easier to start a healthy one. Here in college, there’s a big social pressure to date and a lot of that is ingrained in hookup culture. And it’s okay if that’s not what you want!
Ultimately, the worst thing about dating is that it all comes down to luck. Some people might meet someone they connect with immediately, but for the rest of us, it takes some trial and error. It sucks, for sure, but don’t be discouraged on your second (or third or fourth) try!
Love,
Your Claremont Cupids
Need more advice? Send your inquiries to tinyurl.com/TSL5CShadesOfGrey.
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