How to Approach a Guy

Whitney Gaines
4 min readJul 21, 2021

The Question

I need advice on how to approach a guy. I’m 21, shy, and have been single for a while and I’d like a boyfriend.

Virgo, 21, she/her/hers

Just looking out the window at potential dating partners. Photo by Anthony Tran on Unsplash

The Response

Oh, Virgo, so many jokes have run through my head on this one. Like, have you tried a pokéball? Have you lain out a plate of burgers and a beer (or adult beverage of your choice) outside of your house on the new moon for six months? Have you tried a lasso — maybe try and use Wonder Woman’s because it’s the Lasso of Truth and that will make the “talking phase” much more helpful.

You could try dressing up like [insert thing men enjoy]. Or like cryptocurrency. You could try cooing at them like pigeons, or sniffing their butts like dogs, or using the elk mating call — it’s glorious.

Are these ways to get men? I don’t know.

I completely understand the desire for a romantic partnership, especially as a young woman nearing the end of her college career. The media bombards us with rhetoric around women’s worth being defined by their romantic relationships constantly, and, honestly, that can add to the stress of finding a worthy partner.

I get it. Holding hands is amazing. Kisses are pretty dope. Sex is cool, too, but have you ever had a man treat you with the respect and kindness that you deserve? Me, neither — well, at least not usually both at the same time, and not consistently, and/or not for any sustained amount of time. (There are a LOT of reasons for this, but the biggest one is the entitlement/desire for control by men and also the trauma my father caused. Yay, daddy issues!)

Building a life with someone is one of the greatest joys you can experience. Love, for me, is always worth the risk of heartbreak, because I know that I will love again. Heartbreak is a great teacher. Love is a great teacher, too, though usually in retrospect.

But let me caution you, Virgo, that asking for advice on how to approach a guy — any guy — is not the way to go about creating a healthy relationship. You need to set your standards first, and to know what your standards are, you need to know yourself really, really well. (But you’re a Virgo, so I’m going to assume you’re pretty self-aware)

The Advice

The first thing you should do, Virgo, is to create a list of traits or characteristics or non-negotiables for a potential partner. These are important — you’re not building an ideal man, but you are creating something that will help ensure you’re treated well. Want a partner that responds quickly to texts? Add that to the list. Want a partner who can admit when they’re wrong? Add it to the list. Beware of any man that refers to his exes as “crazy.” Those men are to be avoided.

Now, as for actually approaching a guy? Hooboy, that’s a tricky one. How can you know if any guy you approach has any of the characteristics or traits on your list? You can’t, not really, not until you get to know them more. This is why I like dating apps. For one thing, you can weed out men that you aren’t interested in. For another, you can start conversations with men without giving them your phone number, and you can get to know them to your comfort level before deciding to meet. For another, everyone usually states their intentions up front (dating, a relationship, hook-ups, friendship, or “open for whatever”). And, finally, it’s a great way to meet people when you’re really shy or don't feel comfortable invading someone’s personal space in public (I hate doing that, no matter how cool I think someone looks, because I hate it when that happens to me).

If you want a relationship, I suggest using apps like Hinge, OKCupid, or Bumble.

If, however, you’re like, eep, no, apps are scary! Then you have fewer options, but more that require you to step outside of your comfort zone. Join a co-ed social sports team like kickball! Or a DnD group if you’re a bit nerdier. Or both! Join a gym that has group classes, or a yoga studio. Use your interests as a launching point to finding like-minded men.

And for the actual approach? My biggest piece of advice is not to put the pressure of a romantic relationship on your first encounter with any man. Instead, introduce yourself, say hi, and get to know them with no other intention than getting to know them. That way, you can decide for yourself whether they’re relationship material instead of having that focus the entire time you’re talking. Because if you have that focus, you might miss some important signs. Just say hi, maybe ask them what book they’ve been reading or what music they most enjoy, and see where the conversation takes you.

Good luck, Virgo!

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Whitney Gaines

The advice column no one asked for* from Denver-based queer, biracial writer & educator Whitney Gaines. (*for which no one asked)