Love and Relationships

[Two Pronged] Help! I’m madly in love with my boss!

Margarita Holmes, Jeremy Baer

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[Two Pronged] Help! I’m madly in love with my boss!

David Castuciano/Rappler

'I think about him a lot. My work is centered on pleasing him more than anything.'

Rappler’s Life and Style section runs an advice column by couple Jeremy Baer and clinical psychologist Dr. Margarita Holmes.

Jeremy has a master’s degree in law from Oxford University. A banker of 37 years who worked in three continents, he has been training with Dr. Holmes for the last 10 years as co-lecturer and, occasionally, as co-therapist, especially with clients whose financial concerns intrude into their daily lives

Together, they have written two books: Love Triangles: Understanding the Macho-Mistress Mentality and Imported Love: Filipino-Foreign Liaisons.

Dear Mr. Baer and Dr. Holmes,

Here is my dilemma: I have fallen in love with my boss. I developed this feeling after years of working with him. I never expected to feel this way as I have never developed feelings for my colleagues in all other organizations I’ve worked with. For the most part of our relationship, we were purely professional.

He is fun to be with and very intelligent. I enjoy being with him. On rare occasions he can be very sweet. To my horror, I started having this distinct feeling that I know to be romantic love. I think about him a lot. My work is centered on pleasing him more than anything. I would also feel some jealousy, and I know this is not related to work.

I am not delusional enough to expect that our relationship would move further into a more personal and romantic one. I totally get it. I also would not risk my career by pursuing a relationship with him. 

I had resolved within myself that I would just love him from the sidelines and just please him with good work, hoping this will just go away. However, while this feeling results in me being extra good at my job most of the time, it also sometimes adversely affects it, especially if jealousy is involved or if I am having a problem with him.

My feelings are now so intense that I am already thinking of quitting and moving on. However, I am seriously entertaining this idea of confessing my feelings when I leave the company, though if I do this, I will be ready for possible rejection. I just want to let him know. Would this be okay? I read somewhere that this is not advisable because this might burn bridges.

I am totally emotional. I have never felt a romantic feeling as intense as this. Is there a way for me to manage these feelings more effectively while he is still my boss? Thank you.


Dear Cora,

Thank you for your email.

You have presented a comprehensive analysis of your situation and your options. You have now reached the point where you are contemplating leaving your job, and then it is a question of whether you reveal your feelings. You mention advice about burning bridges, but are there any to burn once you quit? Frankly, if you leave and then never tell your boss how you feel, there is no hope whatsoever of any relationship developing and you will never know what might have been.

If however you do then tell him, you will find out if he too has been holding back because you were work colleagues. You say you are ready for possible rejection, so you will be prepared if your feelings are not reciprocated. There therefore appears to be no downside in opening up to him once he is no longer your boss.

As for managing your feelings while you are still working for him, stick to what works. Just being extra good at your job has been a winning strategy to date, so simply continue until he becomes your ex-boss.

Best of luck,

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[Two Pronged] In love with my married boss… and my boyfriend

[Two Pronged] In love with my married boss… and my boyfriend

Dear Cora:

Thank you very much for your letter. Because of space constraints and also because of Mr. Baer’s letter above, I feel going straight to your questions will be all right. You asked two:

  1. Would it be okay to tell the boss how I feel?

Before I answer this question, there are two issues you have to deal with. The first is for you to find out if what you feel is really unrequited love (UL), which is how you describe your feelings for him, or mere infatuation.   

A good way to decide between the two is to ask yourself how you feel for him. If you feel “I love you because I need you” describes your love better than “I need you because I love you,” then Erich Fromm (and I) describe this as immature love (infatuation). If, however, the opposite is true, then Fromm (and I) feel it’s mature love. If you are merely infatuated, best not to tell him because once you do, it will affect him on several levels, and it would be cruel to do so simply because of infatuation.

In my personal opinion, even if you truly, maturely love him, it is also better not to tell him if he is married. This, of course, depends on your sense of values; admittedly, mine have become more conservative where marriage is concerned. If he is married and has not said or behaved in any way suggesting he is unhappy (or even if he is but wants to keep his marriage), telling him would discombobulate him at some level. Unless, of course, he is a sociopath. Unlikely, given your description. Research has shown that UL becomes a burden not only for the person experiencing it, but also for the recipient, if he knows.  

  1. You also ask, is there a way for me to manage these feelings more?”  

National Certified Counselor Kayce Bragg suggests the following: keeping busy, maintaining a solid support network, and learning to love yourself can help. If you’re having a hard time getting over unrequited love, you may consider working with a mental health professional or writing to Two Pronged, which gives excellent advice (last bit my words, not hers 😊 )!

Personally, I find humor very helpful. Alas, in this case laughing at yourself (but only till you get strong enough that you can — you are not a martyr, after all) and also laughing at the situation.

Happily, I am not the only one who does so. Greve, W. (et al.) in “Humorous Coping With Unrequited Love: Is Perspective Change Important?” in the science journal Frontiers of Psychology Volume 12 (2021) wrote that “a large body of research indicates a positive relationship between humor and psychological well-being” and adds that “a strong sense of humor is associated with, for example, a more positive self-concept and self-esteem as well as higher life satisfaction.”

I agree entirely. In the end, if you have well-being, life satisfaction, and self-esteem, you have a whole lot going for you, UL or not, diba? 

All the best,
MG Holmes


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