to men or not to men…

by isabella castelo

“I really want to find a certain kind of boy after being a girl who has dated women all her life. I have refused to date men based on my bad experiences with them within my life. However, since being in college, I have met the sweetest guys, and I think I want to give it a try. I do fear I am picky with men and quite wary of them. I want to meet a guy, but I truly am not sure how to approach them in a romantic way… any advice?”

Unfortunately for you, I’m a lesbian through and through. Fortunately, however, I tried really hard not to be. Throughout high school, I convinced myself I had a big, fat crush on my best friend, Jake. He’s one of my oldest friends and we always have a good time together—I tell him everything (everything), and he laughs at all my jokes. Truly, my dream man. 

I’d fantasize about us doing cliche couple things—cheesy dates and being connected at the hip (I should’ve known I was a lesbian). Then, one day, I saw a straight couple sitting close to each other, legs touching, really erotic. He held her hand, turned to her, and gave her a quick kiss. On the lips! Instantly, I was shot back to reality. All these years with a “crush,” and not once did I imagine, hope, or initiate a kiss between us. In fact, the mere thought of getting that close to Jake’s face made me squirm. I’ve been a lesbian ever since. 

You’re probably wondering why I shared this since it pretty much says to listen to your gut and stay away from men. If that’s all you needed to hear, then you can stop reading now, you overthinking lesbo. However, if you came for some real answers, I think Jake still offers a lot of insight into your problem. 

He teaches us the most important lesson—how to tell if you’re really into men. If the reason you want to try guys is that you’ve met so many nice, caring, and funny ones, you need to dig deeper and find out if you just really like being their friend or if you seriously want to bang them. Get this out of the way first, and potentially save yourself from years of grief trying to fall for your guy best friend. 

If you’ve imagined getting… intimate and still want to look him in the eyes, it’s time to explore flirting. It sounds like you’ve successfully seduced a woman in your past, and I think you’re overthinking flirting with a man. As a lesbian, there is no way getting a man in bed with you is more difficult than getting a woman to do the same. With a woman, there’s so much nuance; so much investigating you have to do in a matter of minutes to decide if she wants to be your gal pal or your girlfriend.

If you go up to a man and start flirting with him like he’s a woman, either you’ll bag one of those twinky bisexuals (Lord knows there are plenty of those around here), or you’ll scare away boring straight men. I’m team TB (Twinky Bi), but really, you can leave all that extra work behind and melt a man with eye contact—I’ve seen it happen. Maybe show extreme interest in his Spotify if he’s being stubborn. 

I commend you for going out and playing the field. I also commend pickiness if you’re looking to seriously date a man. However, if you’re experimenting, you need to let go of some expectations and some anxieties. The more you overthink flirting and being with men, the harder it’s going to be, when really it’s rather simple. Have more confidence and use your former lesbianism as an ego boost. We’re the best. 

Love, 

Isabella