Dating a shy and socially awkward girl, requires that you are accepting of her.
She is shy and awkward by nature, and isn’t changing any time soon, or ever.
This has to be accepted before moving further with her.
Don’t expect her to magically morph into an outgoing person in dating her.
Setting expectations like this is detrimental to the two of you.
There is no advantage in dating a girl you are looking to change.
With this acknowledged, dating a shy and socially awkward girl is better done when you approach her with something she relates to.
Gain information about a topic you two have a shared interest in and bring it up as a topic of conversation the next time you see her.
Whether it be something to do with a class she takes or what she does for a living, use this shared interest to open a conversation with her.
Advise her about your experience taking a similar class or working a similar job, and be truthful.
Don’t relate to her through fabricated stories.
Fabricated stories are found out eventually and this turns her off.
Hard to trust someone who fabricates stories.
The value of opening up conversations with topics she is familiar with is in how this lets her talk freely about the topics.
The conversations aren’t forced.
She speaks naturally and extemporaneously.
Unlike an extroverted girl who speaks off the cuff about whatever topic, a shy and socially awkward girl speaks with greater fluency when it is a topic she is familiar with.
The fluency of conversation develops an affinity between you over time.
Dating a shy, socially awkward girl, calls for you to create an atmosphere that lends to her feeling enough confidence to be her true self around you.
Shy and socially girls aren’t forthcoming with their true personalities when they are around people they aren’t secure with.
This is where you are better served in being her friend first.
Being around someone she is familiar with and trusts, gives her greater latitude to demonstrate her true personality with you.
Her guard goes down.
In lieu of fearing how you react upon observing her authentic nature behind the shyness and social awkwardness, she is so open with her personality, regardless of her quirks and idiosyncrasies.
Once she has arrived at this degree of comfort with you, she is primed for romance.
Flirt with her.
Tell her how amazing she is.
Give her compliments.
Keep on relating with her on information she is revealing about her personal life.
Ask her questions about her friends, family, roommates, work colleagues, acquaintances, etc.
Remember their names and use those names when you ask her follow-up questions on information she has shared with you in the past.
Doing this builds a stronger emotional bond with her.
Eventually, there is such a bond of camaraderie between you, you are no longer seeing a girl who is shy or socially awkward.
You see a girl who has a dynamic personality that goes beyond the shy and socially awkward exterior that most people experience when they first meet her.