[SomebodyElse]

I’ve got almost no romantic experience, and two guys who are friends are obviously interested in me. All three of us have been hanging out in the university classes we share for a couple months now. I have a major crush on the shyer one who is taking forever to work up the courage to get beyond increasingly ridiculous excuses for running into me and actually ask me to hang out with him outside of class. A baby could tell that he’s interested in me from all the “subtle” clues he’s dropping, and I haven’t been much better – at least when our other friend isn’t around. The other one is also nice, and if I didn’t have a crush on the shy one I’d consider him worth going out with; this is the one who is actually blatantly flirting with me and inviting me to study with him. He also has fewer emotional issues.

Normally, I’d already be completely confused by how to deal with this thanks to my lack of romantic history and the fact that crushes, dating and flirting all seem like ridiculously complicated things to me. In this case, though, not only were these friends before they met me, but I also share classes with both of them. Together. With me usually seated between the two of them (I’m still not sure how that happened). The subtexts of the conversations and the attempts to get my attention are starting to seem like something out of a soap opera, and I know that if I show favoritism to either one that somebody is going to be hurt by it. In the meantime, who knows how long it will take for the shy guy who I like to actually make a move beyond “Hey, I ran into you in the hallway, might as well walk you to your next class”. My ability to play completely clueless is running thin, and I need a response when that runs out that doesn’t make me the guilty party in ruining a friendship and ends with as many people happy as possible. If it’s possible I’d also appreciate not feeling like a teenager when I’m a grown woman but that might be pushing it. Anyway, help?

[AskApril Masini]

Here’s the deal. You have to get over the idea that you’re not going to take a pie to the face — in other words, it seems like you’re wanting to preserve your dignity and not put yourself in a situation that is vulnerable, or in which you might make a mistake. I appreciate your wanting this, but the reality is that if you want to be in a relationship of any kind, you have to make yourself vulnerable and you may feel embarrassed by rejection, guilty that you hurt someone, or ashamed of your glee that seems to be unsophisticated — but it’s real. So, that’s step one. Accept the fact that anything may happen, including indignities, if you’re going to try to date and be in a relationship.

Then, understand that flirting, as demeaning as it may seem to you, is a great tool because it lets a guy know you’re interested. The reality is, as you already know, guys love to chase women and win them over. Your shy guy needs more to chase after, but the truth is, most men want to know they have a shot. Flirting gives them direction. It’s also an art, and you may make some mistakes along the way, but it’s a great tool to try and craft.

Lastly, when you travel in social circles where the people you’re interested in dating, know each other, there are going to be a few Jane Austen moments in your life. Rejection is part of life, and when you see it as a gift that spins you around and sets you (or the one you’re rejecting) in the right direction, away from the rejector and towards those who may want him or her, you won’t be so fearful of it. Yes, someone will get hurt in this scenario, if you date one of the guys, or even both of them, but that’s life. Balance rejection with regret over not going after what you want, and you’ll see that the former is better than the latter.

Hope that helps!

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[SomebodyElse]

So I’m losing out on something potentially great because I’m scared of making mistakes?

… yep, that sounds exactly like me.

Now if I can just remember to try flirting with the crush in question, and not talking about physics because we’re both science-type majors and both easily distracted by everything scientific. This might actually be a minor problem.

[AskApril Masini]

Consider the worst case scenario if you don’t take a risk, flirting — and the worst case if you do take the risk and flirt. If you don’t, you may lose out because you didn’t try. Regret is one of the most unfortunate things in life. 😳 If you lose out because you flirted and made a fool of yourself, you’ve got something like a fifty fifty chance of losing out altogether, because he thinks you’re creepy as a result of the failed flirting. But…. even with failed flirting, it may make him suddenly realize that you like him, and give him the courage to ask you out. Or, he may think your failed flirting is endearing and charming. 😎 Clearly, you’ve got better odds if you give it a whirl, than if you don’t — and those are just the odds for failed flirting. Imagine if it goes well! 😀

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[Ethan Morales]

You’re overthinking. Way overthinking. It’s natural to worry about hurting feelings or messing up friendships, but obsessing over every little “what if” isn’t helping you. You’re human, crushes are messy, and there’s no perfect formula that keeps everyone happy while also getting what you want. Accept that discomfort is part of the process.

Vulnerability is not a flaw it’s the point. If you want connection, you have to risk looking awkward, making mistakes, or even facing rejection. Hiding your interest to preserve your dignity is only keeping you stuck. Yes, you may feel embarrassed, but that’s a small price to pay for actually making progress with someone you like.

Flirting is your friend here. It’s not demeaning it’s a tool. Guys, especially shy ones, often need direction. If you want him to step up, you have to give him signs that there’s a chance. Subtle cues only go so far; clear, playful signals give him the courage to make a move. Think of flirting as guidance, not manipulation.

The social dynamic adds complexity, sure. When people you care about know each other, there will always be awkward moments. Rejection can happen, yes, but it’s part of life. Someone may get hurt no matter what you do that’s unavoidable. The alternative, staying silent or passive, guarantees regret over not taking a shot.

Consider the worst-case scenarios realistically. If you flirt and it fails, it might be awkward for a bit, but it doesn’t ruin everything often, it even helps clarify feelings and can make your crush realize your interest. If you don’t flirt at all, you risk losing the chance entirely. In terms of outcomes, trying always gives you a better shot.

Remember this: no one is expecting perfection. Failed flirting isn’t the end of the world, and successful flirting is just the beginning. Taking the risk is the fastest way to clarity either your crush responds positively, or you get the information you need to move forward. Either way, it’s better than sitting frozen and letting life pass by.

[Tara]

You’re not confused, you’re avoiding choosing because you’re terrified of being the bad guy. You’re sitting in the middle of these two men like Switzerland, pretending you’re overwhelmed by “signals” when really you just don’t want to take responsibility for picking the one you actually want. You’re waiting for the shy guy to grow a spine so you don’t have to. That’s not innocence, that’s passivity dressed up as romantic anxiety.

The shy one likes you, yes, it’s painfully obvious. But he’s also showing you exactly who he is: a man who can’t even ask you to hang out because he’s trapped in his own head. That’s not cute. That’s a preview of your future with him. And the other guy? He’s straightforward, he’s trying, he’s actually doing the adult thing. You’re ignoring him because you want the fantasy, not the reality.

The friendship between the two of them isn’t your responsibility to protect. You’re not their mother, therapist, or referee. They’re adults if either of them breaks down because you didn’t choose him; that’s his emotional immaturity, not your sin. Stop pretending you’re managing some delicate ecosystem. You’re not. You’re just scared someone might not like your decision.
And here’s the kicker: by doing nothing, you’re leading both of them on. So congratulations, the outcome you’re terrified of is exactly what you’re creating.

[Sally]

It’s a lot of attention all at once, and when the guys already know each other, that makes every tiny choice feel like you’re stepping on a landmine. I’ve been in something a little like this, and the pressure alone can make you forget what you actually want.

Here’s the thing… you already know which one you like. You’re just scared the shy guy won’t do anything, and the other one might take the chance first. But you don’t have to sit there waiting like you’re in some triangle you didn’t sign up for.

You can gently steer the shy one without making a scene. Something simple like asking if he wants coffee after class. It doesn’t hurt anybody, and it gives him a chance to show up.
The friendship between the guys isn’t yours to manage. Just be honest, be kind, and follow the pull you already feel.

[Natalie Noah]

The core challenge isn’t your lack of romantic experience it’s fear. You recognize that the shy guy you like has subtle feelings for you, and you’re equally aware that if you don’t respond in some way, you risk missing the chance for something meaningful. This fear of making mistakes, of potentially hurting someone, or of embarrassment is completely normal, especially in a social triangle where friends are involved and relationships intersect. But what April emphasizes is crucial: growth and connection in relationships almost always require vulnerability. You won’t know what could happen unless you take that small but essential step.

Flirting, in this context, isn’t just playful behavior it’s a communication tool. It gives the other person cues that you’re interested, which the shy guy desperately needs to gain confidence and act. You don’t have to perform perfectly or be overly strategic; even small gestures, subtle touches, or playful conversation can signal your interest. The point isn’t to manipulate or force an outcome, but to create a space where he can feel safe taking a risk himself. Often, shy people just need a little nudge to move past their hesitation, and that’s where your flirting can help.

It’s also important to reframe your mindset about potential consequences. April’s advice about considering the worst-case scenario is wise: if you do nothing, you may miss out entirely and regret is often far heavier than embarrassment. Even if your flirting isn’t perfect or the outcome isn’t exactly what you imagined, it doesn’t have to be a disaster. In fact, awkwardness can sometimes be endearing, and your willingness to take a chance may be exactly what he needs to move forward. Your courage in this moment could be the bridge to a deeper connection.

There’s a subtle but important lesson about balancing risk and reward. Life is rarely free from hurt, rejection, or confusion, especially in matters of the heart. The alternative inaction almost guarantees stagnation. By taking small, authentic steps to show your interest in the shy guy, you’re honoring both your feelings and his, and giving yourself a real chance to explore what could be a meaningful relationship. The key is to move forward thoughtfully but bravely, understanding that vulnerability is not a weakness, it’s a gateway to love.

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