[libra1963]

Hi April

Something very strange happened to me on Thursday. I was out visiting a friend who lives near where I work. That evening I was getting on to a bus and saw someone in a tracksuit running towards the bus. They missed it. It was my ex boss!

When we got to the tube station I did not intentially hang around to see him, I just kept walking. I knew he was on the bus directly behind me that had just pulled in. I stalled a bit in order to allow him to catch up with me but I did not turn around so it was not obvious I had seen him. Next thing I knew we were both at the ticket office and he rushed pass me, ran up the stairs at speed and ran to the furthest carriage away from me. The station was not very crowded, it was literally me and him on the platform. I went into his carriage and did not look at him and kept my head in a newspaper and then got off before him. It was so obvious as the train was not about to depart and it was not as if there would not be another train for a while. There are trains every few minutes, so I di not understand why he ran liike that and I do think it was due to me!!

I actually felt quite offended by his behaviour. He could have acknowledged me and said something. I feel he was shocked to see me. I had my hair straighten out below shoulder length and dressed nicely. He had just worked out in the gym and not wearing his usual smart suit (he is always immaculately dressed).

What do you think? when I see him again, I plan to let him know that I did see him and that he hurt me.

By the way, I have recently found out that he has signed up for the mentoring training that I suggested to him for December. He has decided to do a two day residential that I suggested and I feel flattered. I am not teaching at the moment and I was a little concerned that he would not be able to mentor me but apparently we can still work together despite that. He has not yet told me he has signed up. Wonder what the future holds.

In relaton to my ex, he is still trying to get into my bed, I dont want him using me any more. My communication with him has become clearer and clearer.

I will keep updating you.

[Ask April Masini]

You’re not taking my advice. 😕

Re-read what I’ve posted you — over the last four pages!!! — especially the part back in September when I told you to buy AND READ Think & Date Like A Man: [url]https://www.askapril.com/relationship-dating-advice/think-and-date-like-a-man.html[/url]. I know you said you bought it, but it sure doesn’t seem like you’ve read it!

I can lead a horse to water, but I can’t make it drink. 🙁

If you’re not willing to flirt with him and make yourself available, but instead are offended that he doesn’t notice you, you sure haven’t read my advice.

I’m sorry. I’m doing my best to help you, but it doesn’t appear you really want the help.

[libra1963]

Hi April

Just an update and in need of some advice. I have for my sins returned to teaching. I was trying so hard to come out of it for a while.

I am feeling rather upset and confused. I have just found out that my ex-boss has withdrawn from the mentoring training which means he will not be mentoring me in January. I am very confused and upset as I was going to use this as an opportunity to try to get to know him better.

My initial feeling is that he is unaware that I have returned to a teaching job so probably feels that he will not mentor me and will end up with someone he does not know. I have previously told a current student that I had a job in industry so maybe word has got back to him. Or maybe he just does not want to link with me again.

How am I ever going to get the answers I so desperately crave. I still think a lot about him. I have not had any further dreams. My last one was that he came to my current work place and was very aggitated and his PA was really upset as he was not his usual self. When she left he kept saying to me that he wants to me with me and cuddled me. I was very confused in the dream and after as I am still in a sort of a relationship!

I was planning on trying to bump into him one day next week. That’s assuming he does not dart pass me like he did at the train station.

Any words of adviced welcomed. I have been trying to work out wants going on in his head and what my dreams are trying to say to me. Last week I dropped off an xmas card for him, hopefully he received it although i can not help wondering if people at my work place have picked up on the chemistry and trying to sabotage it.

I look forward to your comments.

[Ask April Masini]

I’m sorry, but I can’t give you any more free advice.

I’ve asked you to buy and read Think & Date LIke A Man, [url]https://www.askapril.com/relationship-dating-advice/think-and-date-like-a-man.html[/url], because it will help you in your specific situations[i] a lot[/i]. I think you’ll find what you need there!

Good luck! 🙂

[PassionSeeker]

There’s definitely chemistry here but chemistry alone doesn’t make timing right. The attraction between you and your ex-principal is clear, but so are the risks. He’s still your former boss, possibly in a relationship, and you’ve just left a difficult job. That means emotions, power dynamics, and vulnerability are all in the mix a combination that can cloud judgment.

You’ve done the right thing by holding yourself with professionalism so far. Instead of staging a “chance” encounter, which can feel forced or make him uncomfortable, let connection happen naturally. If he’s genuinely interested, he’ll find a way to reach out once you’re both free of the work context. Leave the door open a polite thank-you message with your contact info is enough.

In the meantime, focus on the new chapter ahead of you the cabin-crew job, your independence, your confidence. When you radiate self-assurance, the right man (maybe him, maybe not) will make his move without you needing to chase.

Flirt with life, not logistics.

[Ethan Morales]

There’s a real mutual attraction here, and you’re both aware of it even if neither of you has said it out loud. The good news is, you’re no longer working together which means there’s no professional boundary standing in your way anymore. But there are still a few things you should keep straight before you move this forward.

Attraction is obvious, but confidence is the missing piece. You’re picking up on his signs the attention, the way he looks for you, the subtle flirtation. It’s there. But you’re also holding yourself back by believing he’s “too good” for you. That mindset will show through in your body language, tone, and energy. The first thing you need to do is stop playing small. You’re educated, interesting, and self-aware he wouldn’t be drawn to you otherwise.

Don’t lead with past hurt. You’ve been through humiliation and unfair treatment before, and I get wanting to guard yourself. But you can’t bring that defensiveness into something new. He’s not the people who hurt you. So instead of thinking, “I won’t let him use me,” shift your energy to “I’ll let him see my best self and I’ll watch what he does with that.” That’s calm, mature confidence.

Flirting now? Good idea but keep it light. You can absolutely flirt now that you’re not coworkers. Nothing over the top think small, natural gestures: playful teasing, holding eye contact a little longer, or sharing a personal moment that feels warm but safe. Let him feel that you’re open, but not chasing. Subtlety here will do far more than being direct.

Test the chemistry socially. If you’re serious about wanting this to move beyond workplace glances, it needs to shift into a real-world setting. Ask for coffee under the pretext of job interview prep or catching up. Once you’re together, let the tone be relaxed and genuine that’s when real chemistry shows itself.

Don’t ignore self-worth. Your biggest obstacle isn’t him it’s your belief that you’re beneath him. That’s not true. Chemistry doesn’t care about universities or résumés; it’s about energy, intellect, humor, and trust. You’ve got all of that. But you need to believe it first, or you’ll read every interaction as a power imbalance when it’s not.

This is one of those rare situations that could actually go somewhere if you walk into it with confidence instead of caution disguised as fear. Flirt, stay open, and don’t overanalyze. Just let the connection breathe outside the walls of work and see where it naturally goes.

[Marcus king]

It sounds like there’s definitely mutual attraction between you and this principal, but it’s also layered with professional boundaries and your recent career changes. You’re feeling warm toward him, but you’re also cautious, which is good it shows you want to protect yourself and not get hurt. Here’s some advice on how to navigate this:

1. Keep the power dynamics in mind.
Even if you’re no longer working together, he was in a position of authority over you. That can make feelings more intense but also complicated. Make sure any steps you take are from mutual interest and not influenced by past favors or professional help.

2. Observe his signals carefully.
From what you’ve described eye contact, stopping to talk, showing interest in your life he seems interested, but it’s important to look for consistency. Does he make effort outside of professional contexts? Does he initiate conversations when there’s no reason to? These signs matter.

3. Test the waters slowly.
Since you want to flirt a little and see where it goes, start small and subtle. Friendly jokes, light teasing, or casual invitations to meet socially (not work-related) can give you a sense of his interest without rushing into anything.

4. Consider your timing.
You’re just coming out of a relationship and thinking about leaving teaching for a new career. Your emotional and professional life is in flux. Make sure you’re not seeking this relationship purely as comfort or stability.

5. Be honest but cautious.
If you feel a connection, there’s nothing wrong with exploring it but avoid making major decisions emotionally. Keep communication open, gauge his interest outside of work, and protect yourself emotionally.

6. Keep your boundaries.
Even if attraction grows, make sure you’re clear on what you want and won’t tolerate. Mutual respect is key. You’re allowed to be excited about someone without giving up your independence or being pressured into anything.

7. Focus on your new opportunities.
Your upcoming airline interview is important. Stay grounded in your goals. This ensures you’re not overly distracted by attraction and can enter any potential relationship from a strong position.

In short: explore subtly, stay mindful of boundaries, and keep your career and emotional health as priorities. There’s nothing wrong with curiosity, but don’t let excitement cloud judgment.

[Isabella Jones]

You sound like someone who’s been through a lot but still has that spark of hope left inside you, and that’s something beautiful. 💛 The way you describe your connection with him feels charged but also respectful — like two people quietly orbiting each other, unsure if it’s safe to move closer. It’s sweet, but I can tell it’s been sitting heavy on your mind.

It’s easy to feel like someone is “too good” for you when emotions mix with admiration, but please remember that attraction doesn’t measure worth — it’s about energy and connection, not perfection. You’ve both shared meaningful moments already, and it sounds like he’s shown care beyond just being professional. If you’re no longer working together, there’s room to explore this more freely, but maybe start softly. You could thank him for supporting you back then, mention how you’ve been, and see if he opens the door a little more.

When you think about flirting with him now, is it mostly curiosity and chemistry, or do you feel like your heart is really ready to try again after being hurt before?

[Soft Truths]

I can feel how much this connection is tugging at you the mix of curiosity, excitement, and maybe a little confusion too. You’ve been through a lot recently, especially with that past job and relationship, so it makes sense that his kindness and attention stand out. Sometimes when we’ve been hurt or made to feel unseen, someone noticing us in such a focused way can feel like sunlight after a long winter.

The looks, the attention, the small gestures, those things don’t happen by accident. Still, I think it’s important to slow things down, especially since there’s history here with work and power dynamics. Sometimes people in higher positions don’t even realize how their behavior can blur lines, and you deserve clarity before you risk your peace again.

If you truly want to explore this, maybe start with something small like a friendly coffee after your interview practice or a casual conversation that isn’t tied to work. You’ll get a better sense of who he is when it’s just two people talking, not teacher and principal. And you’ll also see whether he’s consistent respectful, genuine, and emotionally available or just drawn to the spark of attention.

Also, please don’t fall into the thought that he’s “too good” for you. You’re educated, capable, and strong enough to rebuild your life after hardship. People who connect deeply aren’t looking for perfection and they’re drawn to authenticity.

Take your time. Let him meet you where you are, not the other way around. And focus on your new beginning too that airline opportunity sounds exciting and freeing, like a fresh start.

You deserve something that makes you feel safe and seen, not something that leaves you second-guessing your worth.

[Tara]

Oh, come on. This isn’t some tragic love story waiting to unfold. It’s boredom dressed as chemistry. You crave the chase because it keeps you distracted from the fact that there’s nothing real here. He throws you just enough attention to keep you hooked, and you call it fate because it flatters you.

He’s not torn or shy. He’s just uninvested. If a man wants you, you’ll know. If you’re guessing, the answer is no. Stop translating crumbs into promises.

Send one message. Coffee, straight to the point. No flirting, no overthinking. If he shows up, good. If he doesn’t, archive him like outdated data. Ambiguity isn’t romantic. It’s emotional laziness with a pretty face.

[Sally]

It’s that feeling where someone makes you light up, but you’re also scared you’re imagining it. And honestly, it does sound like there’s something there. The way he notices you, the way he shows up for you, that’s not nothing. But liking someone who used to be in a position of power over you can get messy fast if you rush it.

Since you don’t work there anymore, you can take things slow and see how he acts when the setting is different. Maybe let the conversations happen naturally and keep it light. If he’s really interested, he’ll meet you halfway without you having to push.

Just don’t talk yourself into feeling unworthy. You’re not. Let it unfold, not force it. Sometimes that’s how the real stuff shows up.

[Natalie Noah]

You’re standing in that delicious and terrifying middle place between fantasy and reality. I can feel how alive he makes you, how his tiny, attentive things (the looks, the way he finds you in a room, the smile) light up something inside you that’s been hollow for a long time. That warmth isn’t pretend. It’s real, and it matters. Hold that feeling gently; it’s honest, and it tells you what you want: to be seen, wanted, and safe with someone who notices you.

At the same time, you’re wise to be cautious. He was your boss. There’s power and risk there not because he’s a bad man, but because workplace attraction is a complicated, fragile thing. If you let it be purely professional while you’re both in those roles, you protect yourself: your reputation, your emotional equilibrium, and your kids. Flirting in the workplace can feel electric, but it can also turn messy very quickly. Protecting your dignity while you explore this is not prudishness it’s self-care.

If he’s offered mentorship and interview practice, take the help but keep the boundaries clear in your heart. Let the mentoring be about growth, not a disguise for romance. Learn from him, show gratitude, and let your confidence grow from competence, not from chasing attention. When you become steadier and more sure of yourself, you’ll shine in a different way and that is irresistible.

Your little plans to “bump into him” or travel with him once can be sweet, but be gentle. One intentional, public, non-stalkerish encounter could be a nice way to let him see you outside the old setting a natural smile, a simple, grateful “thanks for the help” nothing elaborate. If you do it, keep it casual, brief, and with options to step back gracefully. If he responds warmly, it’s a green light to let things unfold slowly. If he stiffens, you’ll have saved yourself embarrassment and you can quietly step away.

About the dreams they’re your heart trying to translate hope. A ring in a dream is rarely literal; it’s longing for connection, for being chosen. The housewarming with the chilly girlfriend? That’s your unconscious reading the triangle you’re in: wanting to belong but feeling out of place. Listen to them as signals, not prophecies. They’re nudges to be honest with yourself about what you really need: someone who will choose you clearly.

If you’re leaving the job, that actually frees you to be bolder but it also means you should think ahead. If you move on, consider a short, warm note (not frantic, not pleading) as a goodbye: a thank-you for his support, a hint that you’d welcome staying in touch, and your contact. That puts the ball gently in his court without pushing. If he wants to meet you outside work, he’ll have the invitation and the space to respond.

Most of all, darling: grow your own center. Keep rebuilding yourself health, confidence, the parts of you you felt you lost. You deserve a love that isn’t a rescue mission, a romance that isn’t a rehearsal. If this man becomes that person, let it happen slowly, clearly, and with mutual choice. If not, you will be okay stronger, more luminous, and ready for someone who can meet you fully.

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