Love and Relationships

[Two Pronged] I’m a 42-year-old man with zero experience in romance

Margarita Holmes, Jeremy Baer
[Two Pronged] I’m a 42-year-old man with zero experience in romance
'I’m a 42-year-old man who likes a 25-year-old girl. I like her because she is pretty. I want her to be my girlfriend.'

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.

Hi, Dr. Holmes and Mr. Baer

I like a girl but I don’t know how to talk to her to express how I feel. I don’t know where to start. How can I find the words?


Hi, Antony. We would like to help you, but please, could you share a little bit more about yourself to help us? For example, how old are you (what we suggest to a 48-year-old man might be different from what we suggest to a 21-year-old man). What do you like about this girl? What would you like to tell her? Is it only with her that you can’t express your feelings, or with other people too (about other things)?

Many thanks,
MG Holmes

I’m a 42-year-old man who likes a 25-year-old girl. I like her because she is pretty. I want her to be my girlfriend. I can talk to other ladies because I can joke around with them, but with this girl I’m serious. I want her to see my seriousness and my funny side. Then she will know me better, and we can have fun and a good relationship.

Last one nalang, okay? Again, to help us get an even better picture of you because we can include both your personality and past experiences into consideration.

1.  Have you ever liked a girl before that you had no trouble talking to?

2. If yes, why do you think this girl is different from the others you had no difficulty in speaking to? If no, can you think of anything in your upbringing or any past experiences that may have contributed to your shyness?

Many thanks and we promise to answer you right after getting your answers, okay? 

Warmest regards,
Two Pronged

Q1.  I had trouble with talking to all of them because I think they won’t like me and I’ll get rejected.

Q2. I think it was love at first sight. It’s just that I don’t want to get rejected. No problem with my past or upbringing. I just want girls that have a nice upbringing too, just like me. I think she has it. I want to have only just one girl. If I’m not happy I want to have other partners.

Must Read

[Two Pronged] I’m an older woman dating a much younger man. Can this really work?

[Two Pronged] I’m an older woman dating a much younger man. Can this really work?


Dear Anthony,

Your email has given us food for thought, given the possibility that your inquiry is just a hoax. However, I will try to answer on the basis that you are indeed a 42-year-old man who apparently has zero experience romancing a woman and wants to know how to proceed.

Firstly, a reality check. Bear in mind that romancing a woman 17 years your junior is not necessarily going to be easy, unless you already have indications that she finds you, or older men in general, appealing. Bear in mind too that just because it was love at first sight for you, it doesn’t mean she feels the same. In fact, it seems almost certain she doesn’t because otherwise you would be chatting away and not be in this predicament. 

So, you will not be an obvious choice as a partner, however good your chat up lines may be and however funny you may think yourself. I suggest you keep your goal “to have fun and a good relationship” to yourself as it is unlikely to be attractive or ambitious enough to encourage her to enter into a relationship with you. It makes you sound sleazy and just wanting to bed her on the basis of a few laughs.

If you still want to go ahead, perhaps it is best to start from a place with which you are familiar. You say you have had no problem just chatting with women, but putting such a conversation on a romantic footing leaves you speechless. A solution-oriented approach would be to practice on other women first so that you then have what it takes to go ahead with your 25-year-old. Imagine that you are talking to her while practicing. It would of course be ethical to reveal your true purpose to the women you are experimenting with, but perhaps ethics are not of much interest to you.

Please let us know how you get on; your experiences might be a useful guide to others who find themselves in your position.

All the best,
JAF Baer

Must Read

[Two Pronged] 22-year-old picks between a 57- or 63-year-old

[Two Pronged] 22-year-old picks between a 57- or 63-year-old

Dear Antony:

If the aggression/hostility in Mr. Baer’s answer takes your breath away, you are not alone. I, too, am surprised.

But we are focused on helping you, not him. I am glad, however, that being my initial editor (so that our beloved Rappler editor, Marguerite de Leon, won’t find it too onerous a task), he will read my answer as it may also be grist for his therapeutic mill. 

For the avoidance of doubt, I totally agree with Mr. Baer regarding the best way to talk to your crush (for lack of a better word). In the same way she has to get to know you, you too have to get to know the real her. So practice with other women until you can be more relaxed about speaking with her.

That is the behavioral part. It might be a good idea to explore your emotional side. While you say you have no problems with your past and upbringing, might it be possible that something which, at the moment, might be unimportant to you actually made a bigger impact than you know?  

I say this because rejection is a big issue in your life. True, all of us avoid rejection as much as we can. But few fear it to the extent you do — waiting until 42 to finally commit to doing something about it.

In 2021, the media personality Oprah Winfrey and renowned brain and trauma specialist Dr. Bruce Perry wrote a book that shifted the question (for people who had personal issues) from “What’s wrong with you?” to “What happened to you?”

This is not that new a concept. Social scientists have a term for it: ACE (aversive childhood experiences). The World Health Organization have written at least 10 reports on different countries, spanning 2012-2018.

The latest research I have come across (just yesterday, as a matter of fact) was published this week in the open-access journal PLOS ONE by Dr. Sophie Guthmuller of Vienna University of Economics and Business, confirming that “life circumstances during childhood — including having fewer friends and siblings, low-quality relationships with parents, bad health, and growing up in a poorer household — are all correlated with a higher rate of loneliness.”

Dearest Antony, please forgive me if this answer is truly two-pronged in two ways.

One is the constant fact that Mr. Baer, a retired banker used to getting quick results for the largest financial gain, and I, a clinical psychologist, co-author this column. The other is that, despite your asking simply about behavior, I have expanded the discourse to possible reasons for how you’ve delayed certain behaviors. You do not have to be concerned about ACE at the moment, but anytime you might be willing to explore its possibility in your life, please write to us again?

Warmest regards,
MG Holmes 


Please send any comments, questions, or requests for advice to

Add a comment

Sort by

There are no comments yet. Add your comment to start the conversation.