DEAR SHAMELESS

BY SHAMELESS HEATHER ATLES

Hi, I’m Shameless Heather Atles, an expert relationships, sex, and intimacy coach. With years of experience guiding individuals through the complexities of love, connection, and self-worth, my approach combines humor, practical wisdom, deep insights, and actionable steps to empower those navigating the twists and turns of modern romance. 

Ask me anything! hello@heatheratles.com

Dear Shameless,

I recently clicked with someone in a new social circle and we’ve been having a great time together in a relaxed, casual way. The thing is, I’m not the best at figuring out if the signals are saying ‘friends only’ or ‘romantic potential.’ I like making new connections, but San Francisco has so many diverse forms of relationships, I can hardly keep up.

I truly value the bond we’re building, but I’m treading carefully because I don’t want to misinterpret her signals and make things awkward. How can I subtly gauge her true intentions without putting our blossoming friendship in the danger zone?

~Perplexed And Not Pressing

Dear Perplexed And Not Pressing,

You’re not alone. Navigating modern dating (when it’s not even clear if that coffee hang out was a date???) without sending out the dreaded ‘creepy’ vibe — it’s a fine line to walk, especially in the post-#MeToo era, when more attention is being paid to the things women have historically had to endure. 

Your thoughtful approach to this budding friendship — being open to where it might lead without necessarily pushing for a romantic outcome — speaks volumes about your respect for both the connection you share and her feelings. Kudos to you for approaching this with a blend of curiosity and caution. It’s wise to tread gently, especially when a valued friendship could turn awkweird. 

Here’s how you can subtly explore her interest without stepping over boundaries or sending the wrong signal.

Image by Heather Atles with AI since we, surprisingly, couldn’t find a decent Creative Commons photo.

Act Like a Private Dick, Not a Total Dick

Observe with an eagle eye (like a private eye, or is that too many metaphors?) How does she interact with you compared to the rest of the flock? Does she save those sparkling smiles just for you, or are they flying everywhere like the feathers from the Embarcadero’s annual Valentine’s pillow fight? Noticing these little nuances can give you a sneak peek into her feelings without having to swan dive headfirst into the deep end of Dicksville.

Dig a Little Deeper 

Swap out the small talk for something more authentic. Peel back the layers of the artichoke; the heart is the best part, and worth the effort! It’s all about letting your guard down and inviting her to do the same. Think of vulnerability as the secret password to a hidden speakeasy of deeper connection—it’s where all the interesting stories and genuine bonds are found.

Flirt with Finesse

Now, onto the gentle art of flirting—the spice of the courting ritual. Think of it as seasoning a dish; too little and it’s bland, too much and you’re overwhelmed. Taste test the sauce with some playful banter or a light, teasing compliment. Make sure you check in on whether she’s eating it up or sending it back to the kitchen.

Photo by Erik Mclean on Unsplash

Up the Ante

If you’re feeling lucky (or ready to take a calculated risk), why not raise the stakes a bit and invite her on an outing that’s a bit more intimate? I’m not talking about going all in with roses and a romantic dinner, more like rolling the dice with an offer for a one on one time if all your interactions have been in a group setting. Watch her reaction closely—like a poker player reading their opponent. Is she excited about the idea of it just being the two of you? If she’s getting out her google calendar, you might just hit the jackpot. If she hesitates or folds, then perhaps it’s best to check your cards and play the friendship hand for now. Either way, you’re playing it smart—no bluffing needed here.

Photo by Zetong Li on Unsplash

Clearing Up Cuefuesion

If she is sending mixed signals, you might just have to cut through the fog and bullshit, and seek some real clarity. Ultimately, Perplexed, while you’ve been playing it cool and collecting clues, there comes a time to find out whether the weather is clear and sunny or if you need to pack it in and find shelter for the storm. Either way, it sounds like you are the type to check the forecast before you allow yourself to get too attached to any outcome. 

It might be scary, but try being light but direct: “Hey, I like spending time with you but I’m confused about what’s up between us. Are we in a buddy movie here, or do you think we might be heading towards a romantic comedy? Either way, I’m enjoying the script!” This approach keeps the door open for all possibilities, allowing her to step into whichever scene she prefers, with no pressure.

As you already know, pressure is definitely creepy.

With love,

Shameless

Broke-Ass Stuart works because of reader support. Join us now.

Howdy! My name is Katy Atchison and I'm an Associate Editor for Broke-Ass Stuart.

I want to take the time to say thank you for supporting independent news media by reading BrokeAssstuart.com. Supporting independent news sources like Broke-Ass Stuart is vital to supporting our community because it amplifies the voices of a wide variety of diverse opinions. You also help support small businesses and local artists by sharing stories from Broke-Ass Stuart.

Because you're one of our supporters, I wanted to send over a pro-tip.

Our bi-weekly newsletter is a great way to get round ups of Broke-Ass Stuart stories, learn about new businesses in The Bay Area, find out about fun local events and be first in line for giveaways.

If you’d like to get our newsletter, signup right here, it takes 5 seconds.