Ask Shilpa – When is the right time to share my insecurities?

Dear CS-

I’m a late 20-something living in a suburb of a big city.  I’m pretty successful working in finance with a few start-ups under my belt.  I’ve been talking to a girl I met through a friend for about 3 months.  I think things are going really great. She is really independent and we get along really well. 

The problem is I think I’m kind of insecure.  I’m slightly overweight and I have a small gap in my teeth, both which aren’t the biggest deal, but both that I’m utterly self conscious about.  I don’t think she really notices either because things have been going really well.  We’ve been on a few dates so far, but neither of us has expressed ourselves physically and now I’m wondering if I should come clean about my insecurities. 

This is one of the first times I’ve actually liked someone and I’m nervous about sharing my insecurities so early in the relationship.  I don’t want her to think any less of me, but I want to be open with her.  Do you think I should open up about my insecurities?  If so, when is the appropriate time to do so? 

~In Secure

Dear IS-

I think it’s great that you are open about what you are insecure about.  There are people who go through life without admitting to themselves that they are insecure about anything and end up unhappy.  So kudos, you have accomplished a terrifying feat and now you can work it out.

Be honest with yourself before you tell anyone anything about yourself.  Does she need to know?  You are only into this 3 months.  This is the time that everything is going well no matter what happens.  That being said, you don’t know what will happen in another 3 months.

The bottom line is that it is a bit too early in the relationship to start thinking about pouring out your deep dark secrets.  When things get a little more serious and you’ve established a sense of trust and what I like to call “relationship security” (going steady), I think it’s okay to divulge some of your inner most secrets.  This is the actual trust building of the relationship.  If you two can take each other seriously, it may actually work out.

There is never a good reason to jump right in and tell someone everything about you.  It’s just not necessary and frankly not good practice.  Don’t scare someone off by telling them every single one of your anxieties when you don’t know what will happen in six months.  Keep things under wrap until you are comfortable to share what you want.  It’s a communication thing, you will know when you feel comfortable sharing.  Generally it’s a progression of sharing between the two of you.

In the end, if she is really into you, no matter when you tell her about your insecurities, she’ll stick by you.  And anyone who has any type of insecurity (everyone) will understand and probably share your sentiment.  No matter what, if you feel like you are holding something back, then by all means express yourself (a la diplo) and communicate.  In the end, it’s your instinct (cliché, but true) that will tell you when the right time is.


Have a question? Need some advice? Email Shilpa at – You won’t regret it!

She’s honest, she’s direct and she’s controversial. Meet Shilpa, that NYC legend that everyone dreams about but never believes exists. A pre-med drop out, Shilpa received a graduate degree in Human Sexuality concentrating on sex, dating, and relationships. Outside of her obnoxious theories, she enjoys boxing, hip-hop, and her cat, Scandal.  Speaking of scandal, Shilpa has her own blog called ControverSHIL detailing her own scandalous exploits.

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