[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]http://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]http://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.

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