[Ask April Masini]

[quote]So what does this girl want from me? We’re both in our early 30s, is hard to get still a thing? Do woman really want to be chased like this? [/quote]

Yup. So is competition. Chances are you’re not the only guy who’s asking her out. And if she’s single in a big city, she’s probably got a busy work life, a family life, and a social life — with limited time to conduct it all in. You may be mistaking her hesitance as playing hard to get. It may actually be the fact that she’s got a lot going on and limited time. Enjoy what you have — and keep going in that direction. It sounds like it’s working, even though you have a few complaints. The big picture seems to be a good one! 🙂

[Dom1]

Thanks April. That was what I thought, enjoy what you have, don’t give up on it and see what happens. I have basically fallen in love with her, as much as I don’t want to admit it. So we had a little talk the other day before I read your advice. She had been really blowing me off for over a week. So I told her the situation between us was getting a little frustrating for me. She did have a lot going and if that’s all it was that’s ok, but I was getting the vibe that she wanted me to go the hell away, despite how good a time we had when we went out. Basically she said yeah, she has a great time spending time with me, but has the impression that I’m after more than she has to offer (re mostly liking girls), and that it feels a little selfish to hang out with me and encourage something that isn’t likely to happen. Like she would just be creating more frustration for me. And I got that. I told her what I told her before, that I had a totally reevaluated my intentions, and hanging out with someone that really makes me super happy is ok. If that’s all I get, than I should enjoy it, instead of being annoyed that it’s not perfect or exactly what I want it to be. Just enjoy it, for however long I can have it. I don’t know if that’s right, I really don’t. I don’t know if at this point in life I should still be looking for something that is exactly what I want it to be, or just be grateful when someone comes along that I’m attracted to, and like being around, and just try to enjoy it. Even if in the long run in very likely to get hurt or frustrated. Any thoughts on that?

[Ask April Masini]

[quote]If you re-read these three pages of your questions and my advice to you, it doesn’t seem like you really want to take my advice. 😕 I suggested you ask her out, in person, and if she doesn’t go on a date with you, then move on. Instead, you’ve invested a lot of time and energy in someone who’s not interested in the same thing you are. It’s time for you to move on and focus your energy elsewhere. 😉[/quote]

[Ethan Morales]

Alright, let’s unpack this carefully, because there’s a lot going on here and it’s important to separate signals, intentions, and the reality of the situation.

Here’s what I see: She clearly enjoys your company and there’s chemistry

Extended eye contact, big smiles, wanting to be near you at happy hour, engaging in solo lunches these are all strong signs she’s attracted to you.

Her reaction to your gifts and teasing about letting you take her out also shows she enjoys the attention and flirtation.

She is emotionally unavailable or complicated right now

When you asked her on a proper dinner date, she didn’t flat-out say no she said she’s in a “complicated” situation.

That’s a huge caveat. It might mean she’s seeing someone, dealing with personal issues, or just not ready for a serious relationship.

The fact that she left hints about a “boyfriend” ambiguous (like having dinner with her sister on Valentine’s Day) leaves room for interpretation. It’s a gentle way to signal that she can’t fully commit but she didn’t reject you outright.

Your instinct to “play it cool” vs. “be genuine”

Here’s the key: you don’t need to ignore her, but you do need to set boundaries for your own emotional health.

Don’t chase her constantly or put yourself in a position where you’re waiting on her decision. Instead, keep interactions fun, light, and playful the way you naturally are.

Let her come to you sometimes. This gives her space to process what “complicated” means without pressure.

Next steps for clarity

You can casually ask what she means by “complicated,” but do it gently not like an interrogation, more like curiosity.

Suggest a low-pressure, exploratory outing: drinks, a walk, a coffee after work something where you can hang out, have fun, and see if there’s a path forward.

Avoid romantic “full-on” dates right now the goal is understand the situation and see if she’s open to dating in the near future.

Your emotional health matters

You mentioned being crushed and even getting sick that’s a signal your emotions are running very high.

Take care of yourself, don’t over-invest until you know the landscape. Being calm, confident, and self-aware will make you even more attractive.

She likes you but she’s not free or ready yet. Don’t treat it like rejection, treat it like a pause or a “wait and see.” Keep being charming and genuine, keep it light, and look for opportunities to explore her situation without pressuring her. Your goal right now isn’t to win her over immediately it’s to gain clarity and keep the spark alive.

[Maria]

Dom, you’re overthinking this woman into a fantasy. What she’s shown you is hesitation, mixed signals, and emotional games. When someone says their situation is “complicated,” that’s code for unavailable. Maybe she’s attached, maybe she loves attention but not connection, but either way, she’s keeping you hooked while staying safe. You’ve already twisted yourself in knots trying to decode every text and glance. That isn’t attraction anymore; it’s anxiety.

The truth is, when a woman genuinely wants to see you, you don’t have to chase, guess, or wait for her to “figure things out.” She shows up. She makes time. She’s clear. You deserve that kind of woman, not one who makes you feel confused and small. Let her go gracefully, hold your head high at work, and focus on what’s next. The right one won’t make you feel like you’re begging for a chance to be seen.

[Marcus king]

Hey there

Honestly, you’ve handled this with a lot of class already. She clearly likes you, but whatever “complicated” situation she’s in means her timing isn’t right.

Don’t ignore her completely, that’ll feel fake. Just ease off a bit. Be friendly, stay confident, and let her see you’re not crushed or waiting around. Keep things light at work, no pressure, no flirting for now. If she sorts out her situation and truly wants something, she’ll make it known.

stay yourself, but protect your energy. Right now, it’s her turn to show up, not yours to chase.

[PassionSeeker]

Okay, let’s just take a breath, because wow… this one’s tangled, but not hopeless.

First off, I get it. When the connection feels that electric, it’s hard to accept “it’s complicated” as the wall between you. You saw chemistry, she felt chemistry, but what she’s showing you now is that she’s not emotionally available and that’s not something you can fix by trying harder.

Here’s what I see: every time you step back, she notices. She reaches out, re-engages, gets playful again. That’s your clue that she likes the attention, but she’s still not ready to move toward something real. So right now, the power shift has to come from you.

Don’t chase. Don’t over-explain. Let your silence speak confidence. If she wants to see you, she’ll find a way. But if you keep offering yourself up, she never has to make that choice.

So yes stay kind, stay grounded, but stop volunteering for confusion. You already proved your interest. Now prove your standards. That’s what keeps your dignity intact and ironically, that’s when most people finally show their cards.

[Author]

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