[inmyheaad]

My guy friend and I both like each other. Though I’d love to go out with him and be more than friends (we’ve only known each other for 2 months), I am worried that he might have unhidden feelings for a former crush/fellow co-worker. She’s our shift supervisor and has a boyfriend. He admitted that he had a crush on her a year ago when I asked him, but she had a bf at the time. Sure, he may say that he’s over her, but I have this feeling that he doesn’t. If he sees her all the time at work, how can those feelings just go away? They also meet up for drinks with other co-workers after work, too. If she were to be single, wouldn’t he try to pursue a romantic relationship with her then? A scarier thought is if she liked him as well.

I feel inferior compared to her, scared that I’ll lose him to her and it’s why I’m reluctant to risk putting myself in a situation where I might end up getting hurt. To my knowledge, he hasn’t said or done anything that would be a legitimate concern. Everything is just based on isolated events (ex: he asked her for a ride home instead of asking someone else) and gut feelings. I’m intimidated by her mostly because she’s physically attractive. When I asked why he liked me, he said that I was a cool gal, he liked spending time with me, and we shared a few common interests.

He has never dated before and neither have I. We’re both very different people. He’s an extroverted, social Aspie (though he comes across a quirky neurotypical) who gets along with everyone. I’m reserved, somewhat anti-social, and overly anxious. I don’t understand what part of my personality that he likes. Yeah, we talk about his interests a lot. I may not be passionate about them, but I appreciate them and like talking to him about them. Because I have a poor image of myself, I’m very insecure and don’t know if I should become romantically involved with him. I can’t tell if I’m letting my insecurities cloud my judgement or ability to objectively perceive things as is.

[AskApril Masini]

Dating is competitive, and I understand that you’re scared of rejection, but that doesn’t mean you shouldn’t try to get his attention. I think you should compete for him. If you never try, you’ll feel much worse than if you try your best and lose out. So take a big picture view of dating, and give this your best shot. Since you’ve only known him for two months, give him some hints that you’d like to go out with him. Believe it or not he may be having anxiety about being rejected by you! So try to make sure to let him know you’re interested by flirting and mentioning things you’d love to do — like, you’d love to have a date for New Year’s Eve! Or that you’d love to have a date to go ice skating with or to see a new movie with. Use the D (date) word so that he doesn’t confuse your flirting with friendship.

And since you have some self esteem issues, face them. Don’t let them win. If you feel poorly about yourself, do small things that may sound silly but that will help you feel better about yourself. Get dressed up. Read a book that he likes, so you can talk to him about it. Accentuate your best assets — if you’re funny, show him how funny you are. If you’re clever, show him how clever you are. If you’re a good dancer, show him a few move, fooling around. Pick one or two things you know you’ve got going for you, and focus on those strengths. What’s most important is that you don’t let your feelings about your self esteem sideline you. Life is tough, but that doesn’t mean you should sit this one out. Get out there, and let him know you’re looking for a date like him! 😉 I hope that helps. Let me know if you need more help.

[PassionSeeker]

You like someone who also likes you that’s the spark. But instead of warmth, you’re feeling the tremor of what if. The supervisor becomes a symbol, not just a person she represents everything you fear you’re not: confident, experienced, magnetic. Comparing yourself to her isn’t really about her at all; it’s a mirror for your self-doubt.
When you imagine losing him, what you’re actually fearing is the validation of an old belief “I’m not enough.” That fear can make you interpret neutral details a ride home, casual conversation as signs of threat. It’s not evidence of betrayal; it’s evidence of how fragile self-worth can feel when love is new.

[Val Unfiltered💋]

babe..don’t let your insecurity get into you. either shoot your shot or walk away, but don’t sit around playing detective in your own heartbreak. 💅✨

[Heart Whisperer]

I can feel how much this weighs on you that mix of hope and fear that comes when you start caring for someone. You’re not wrong for being cautious; your heart just wants to be safe this time. But what I’m hearing most in your words isn’t about him, it’s about you doubting whether you’re enough.

You are.

Attraction doesn’t vanish overnight, but it also doesn’t mean he’s still emotionally invested in her. Sometimes, a past crush stays familiar simply because it’s part of the same environment not because those feelings still hold power. What matters more is how he treats you now: the way he shows up, listens, and makes time for you.

The part of you that’s anxious and insecure is trying to protect you from being hurt. That’s natural. But don’t let that same part rob you of something that could grow into something beautiful. Love isn’t a guarantee; it’s a risk we take when someone feels worth it.

Before you decide whether to move forward, ask yourself this:
Do you want to build a connection based on fear of what you might lose, or faith in what you both could create together?

Because when a man truly likes you, he’ll make that clear not through words about the past, but through consistency in the present. Watch that, trust what you see, and remember: confidence doesn’t come from being the prettiest woman in the room, it comes from knowing your heart is genuine and that’s what lasts.

[Ethan Morales]

Your fears about his former crush. You’re worried he might still have feelings for your co-worker, and that’s natural especially since she’s attractive and they interact at work. The key thing is: he hasn’t shown any behavior that indicates ongoing romantic interest. Asking her for a ride or meeting for drinks with coworkers is very normal workplace/social behavior. It doesn’t automatically mean he’s emotionally invested in her. Right now, your fear is based on “what ifs” rather than evidence. It’s understandable, but it’s mostly projection from your own insecurities. Opinion: You’re letting hypothetical scenarios influence your judgment more than his actual actions. It’s okay to be cautious, but don’t let fear stop you from pursuing a real opportunity.

You’re comparing yourself to her physically and socially, and that’s affecting how you see your chances. He’s already expressed that he likes you your personality, shared interests, and your connection matter more to him than a superficial comparison. April Masini’s advice is spot-on: focus on your strengths and what you bring to the table. Humor, kindness, curiosity, thoughtfulness these are far more important in a real relationship than looks or popularity. Opinion: If you try to “compete” in ways that don’t reflect your true self, it will feel exhausting and artificial. Instead, let your genuine personality shine. That’s what made him like you in the first place.

You’ve known each other for 2 months that’s enough time to gauge chemistry. Both of you are inexperienced in dating, which means some nervousness and second-guessing is normal. The best step is to signal interest clearly. Flirt, make plans, suggest an activity together, and use the word “date” so it’s unmistakable. This gives him the signal that you want something romantic. Opinion: Waiting too long because of “what ifs” or self-doubt will make you miss your chance. The earlier you communicate interest, the clearer things will be for both of you.

Yes, dating can feel like a “competition,” but it’s really about mutual choice and compatibility, not defeating a former crush. If he genuinely likes you and enjoys spending time with you, the past crush doesn’t matter. If he does end up having lingering feelings, that’s something you’ll learn over time. For now, focus on what’s real: his behavior toward you, the connection you share, and how you feel around him.

You should pursue a romantic relationship if you like him the evidence of his interest outweighs your fears. Keep your insecurities in check by focusing on your strengths and letting him see your genuine personality. Don’t overthink the former crush it’s normal to feel anxious, but don’t let it dictate your decisions. This is a real opportunity for you both to explore something meaningful. If you act thoughtfully and confidently, you’ll never have to wonder “what if” later.

[Tara]

You’re manufacturing a threat because it’s easier to blame a fictional rival than admit you’re terrified of being chosen. You’re not fighting for him you’re fighting to preserve the narrative that you’re unworthy, because it saves you from the discomfort of actually showing up.

He’s not pining after some girl with a boyfriend; that’s just the fantasy you cling to so you don’t have to risk looking confident for five minutes. If he wanted her, he would’ve moved a year ago. He didn’t. The only person stuck in the past is you.

Right now, you’re the obstacle. Not another woman, not his intentions you. Your insecurity is doing the heavy lifting while you pretend it’s intuition. It’s not. It’s self-sabotage dressed up as caution.

[Serena Vale]

Honestly, nothing you’ve said makes it sound like he still likes her. It sounds like your anxiety is filling in blanks that aren’t actually there.

He had a crush on her a year ago. That’s normal. People get over crushes. If he still wanted her, you would see real signs, not “he asked her for a ride once.” He wouldn’t be spending this much time with you, telling you he likes you, or wanting something more.

He’s choosing you because he enjoys you. Not because you’re loud or outgoing or “perfect,” but because he actually feels good around you. That matters more than you think.

The issue here isn’t him or her, it’s how you see yourself.
You’re assuming she’s better because you’re insecure, not because he’s given you any reason to worry.

And look, I get it. When you’ve never dated and you don’t feel confident, it’s easy to think, “Why me?”
But sometimes the answer really is as simple as: because he likes you.

If you like him too, give this a chance. Slowly. No pressure.
Don’t walk away from something good just because you’re scared of a hypothetical situation.

He hasn’t done anything wrong.
Your fears are real, but they’re not facts.

Let the reality guide you, not the “what ifs.”

[Serena Vale]

Honestly, nothing you’ve said makes it sound like he still likes her. It sounds like your anxiety is filling in blanks that aren’t actually there.

He had a crush on her a year ago. That’s normal. People get over crushes. If he still wanted her, you would see real signs, not “he asked her for a ride once.” He wouldn’t be spending this much time with you, telling you he likes you, or wanting something more.

He’s choosing you because he enjoys you. Not because you’re loud or outgoing or “perfect,” but because he actually feels good around you. That matters more than you think.

The issue here isn’t him or her, it’s how you see yourself.
You’re assuming she’s better because you’re insecure, not because he’s given you any reason to worry.

And look, I get it. When you’ve never dated and you don’t feel confident, it’s easy to think, “Why me?”
But sometimes the answer really is as simple as: because he likes you.

If you like him too, give this a chance. Slowly. No pressure.
Don’t walk away from something good just because you’re scared of a hypothetical situation.

He hasn’t done anything wrong.
Your fears are real, but they’re not facts.
Let the reality guide you, not the “what ifs.”

[Sally]

When you like someone, every tiny thing feels like a threat, especially when you’re already feeling insecure. But from everything you wrote, none of your worries are based on something he’s actually doing now. They’re based on fear. And fear loves to build stories out of nothing.

Here’s what I see: he likes you for you. Not for being the loudest or the prettiest or the easiest to read. He likes you because you make him feel good when he’s around you. That’s enough. People do not spend this much time talking with someone they’re not interested in.

As for the supervisor? If he wanted her, he would’ve tried a year ago. He didn’t. And choosing someone else once they’re finally single is not how real feelings work.
You’re not competing with her.

You’re fighting your own doubt.
If you like him, take the chance. You’ll regret silence way more than honesty.

[Natalie Noah]

You’re navigating feelings for someone new while being acutely aware of a potential “competition” in the form of his former crush. Your concerns about his lingering feelings for her are valid, but they’re mostly hypothetical. From what you describe, he hasn’t acted in a way that shows current romantic interest in her. Sometimes our minds focus on worst-case scenarios, especially when we feel insecure, and that can make us doubt the reality in front of us. Right now, what you do have is a guy who likes you, spends time with you, and shares mutual interests. these are real, tangible signs of connection, not just imagined threats.

What April Masini suggests about taking action and showing interest is really important here. Your insecurities are clouding your judgment, making you hesitate, but letting them dictate your behavior could actually prevent a potential relationship from developing. Flirting, suggesting activities, and being clear about wanting to spend time with him are ways to communicate your interest directly without feeling like you’re competing with his past. And the beauty of this is that it gives him the opportunity to respond to your signals. If he reciprocates, it solidifies your bond and makes hypothetical worries about the past crush less relevant because your relationship becomes the priority.

Focusing on yourself is crucial. The small confidence-building steps April mentions accentuating your strengths, showing your humor, cleverness, or talents aren’t just about impressing him; they’re about reinforcing your own self-worth. When you feel good about yourself, you naturally radiate confidence, and that confidence is magnetic. In this situation, your goal isn’t to “win” a competition against her, but to be fully present, authentic, and engaging with him. That mindset shifts the dynamic from fear and doubt to empowerment and opportunity, which is exactly where you want to be when pursuing a new relationship.

[Member]

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