Dear Franco:

“I fear she might reject me due to my inexperience… The feeling of shame is overwhelming… This situation stems from a past rejection that led me to avoid pursuing relationships, causing my insecurities to mount… The rejection hurt so much at the time that I don’t pursued any romantic relationship“-

– the past rejection you experienced hurt you so much indeed. I am sorry that you experienced so much hurt. And I am sorry that as a result, you experience mounted insecurities, fear and shame.

“Recently, I met a woman… I’m open to any advice.“- the woman you met, I bet she experiences insecurities too, that she is afraid as well. Maybe she experiences painful shame, or knows someone who does, someone she cares about, and she feels empathy for that person. Maybe when she sees you being shy or whatnot, she’d feel empathy for you too.

When I was young, I was drawn to shy young men, not to the confident macho kind. And I did not like those who had girlfriends before because that made me feel jealous. Maybe the woman you met would be delighted to know that you lack experience with other women (I would have been, in her shoes).

“I… am sociable, and run a small business“- she may be impressed that you run a small business and that you are sociable, and this may be her focus (different from your focus, which is the experience you lack).

“I was thinking of going to talk in person where she works, when she is alone in the shop, to break the ice, and after a few days, send a message on Instagram and tell her that I like to know  her better, if She seems interested I will ask her out for a coffee or a drink“- reads like a good plan to me.

My advice: get to know her as a friend to begin with, little by little. Pay attention to what she values, to what she thinks is important in life. See if there is a compatibility before you consider the possibility of a physical relationship.

anita