Will Smith is quite the complex character when you look into things. As far as his personality on the outside goes, he's generally a laidback, wise-cracking, confident, and street-smart teenager. However, looking beyond the surface, we see a boy who is very emotional. Although trying to act tough, and as if things don't bother him, they do. Despite the front he puts on, he's very emotional - and cares much more than he's willing to admit. And when you look deeper, it comes from a place of loneliness.

According to Will himself, he was born and raised in West Philedelphia with a single mother, and as we later find out, a father - who left when he was three. As he tells Uncle Phil in Season 4 Episode 24, (keep that episode in mind, I'm going to be bringing it up a lot) he raised himself. With his deadbeat father never returning during his time in West Philly, and his mother always working, Will felt, and I quote - "like he was a boy with one skate, while the other kids were using two." He raised himself, and always felt as if he was inherently lacking something other people had.

If I may use a quote from a psychology study - "Studies have shown that if a child suddenly loses a parent - or parent(s) - through death or abandonment, the child experiences intense fear, panic, grief, depression, helplessness and hopelessness. The child has lost his parents - his lifeline, and often his sense of self

The world, and life, become disorganized and terrifying."

Although he almost never admits it, his life growing up with an absent father played a huge part in shaping him. Because his father wasn't around, and his mother raising him infrequently because she was working as a single mother to support the two of them, Will also had to learn to rely on himself. This not only explains where the root of his bravado of toughness comes from, but also does a great deal to contextualize that, while he did have a sweet relationship with his mother, it is only natural Will would feel lonely, in a sense. If how he references himself in Philadelphia shows us anything, he was quite "the man", having lots of friends, as well as being very attentive and focused in school. Yet, having a single mother working so hard to barely support the two of them, he was subsequently left to be raised by the streets. This is likely why he's so aware of the problems black people face, why he is so aware of why the police arrested him and Carlton in "Mistaken Identity", as well as why he actively jokes to deny the trauma he himself faces when getting shot. He was raised with no consistent parental influence, as his mother was mostly working to support the two of them, so evidently, a lot of his values are rooted in the experiences he had to witness being raised in the streets. Although, I do want to note that despite the fact that he is certainly aware of these issues, and to some extent hardened by them, he does seem to have a generally high view of himself, as well as his childhood in Philadelphia. He is proud about the fact that he grew up in West Philly, and has a deep fondness for his mother and the friends he made in Philadelphia. However, many episodes do at the very least hint at the fact that he recognizes himself as having been "lucky" to have escaped the cycle of discrimination, abuse, and poverty within the ghetto he grew up in.

However, if the influence of being raised on the streets affected Will, then his love life is even worse. Will, throughout the series, is seen to be superficial up until Season 4. Going after girl after girl, never seeming to form a genuine relationship. Looking into his past, it makes sense why he would act this way. Growing up, he only had a mother, and thus, with no father in his life - he never got an understanding of what love was like. Though Will is certainly a charismatic guy, Will's lack of understanding of genuine connections is likely rooted in these circumstances of his childhood. Having a deadbeat father and an absent mother, as she was working to support the both of them, left him predisposed to the very superficial and womanizing mentality perpetuated by the streets. So as far as forming genuine romantic connections went, he keeps his heart hidden, never truly understanding relationships as a young boy in Philadelphia. As a result, his naiveté to romantic connections, which is usually shown to a child through their parents - something Will did not have- prevented him from truly understanding romance, and by extension, prevented him from wanting a deep, intimate relationship. This is out of a misunderstanding of love from his upbringing. He never commits, and his only experiences with love are the one-night-wonders we meet through the series. This perspective also re-contextualizes why he's so damn careless about some of the serious shit he pulls in his womanizing. Having sex with your girlfriends mom, not to mention your Uncle's crush in high school, or even going as far as to plotting a fake marriage to have sex with an abstinent girl - these actions are not something just about any sexually interested male could do. Though I nor the show justify Will's actions, and the show ultimately frames him as reprehensible and despicable for these actions, but given the context of him not having a proper parental relationship to teach him the basics of love and commitment - only having the streets to rely on - it is understandable why he would preform these actions.

In Gemini Man, Will Smith plays a character who's past was similar, if not exactly like Will's - so if I may use a quote from that to help illustrate my point.

"You're dying to really connect, but terrified to let anybody near you. Because what if they saw who you are? How could they love you?" - Henry Brogan (portrayed by Will Smith)

This quote, in a dramatic sense, is more fitting to Will's veneer of confidence and indifference he demonstrates after his father leaves him. But it also contextualizes, at least part, why Will has such a carefree, uncommitted attitude regarding commitment in general.

What understanding these factors of Will's character do is paint the portrait of someone who's flippant, stubborn, and confident bravado is so ingrained in his psyche, that it springs to defend him in any instance. He never had a frequent parental influence, and being raised by the streets, he was never able to properly learn commitment and responsibility. With this in mind, it actually gives a lot of context to what Will says to Carlton in bed that one time - that he "can't see himself with the same woman everyday." It's the reason why he's such a womanizer. This would also be why, AFTER Season 4, the season where he confronts his abandonment issues, he actually actively pursues a love life with a girl he meets, Lisa. Though the issues regarding his father will always be a part of his life, through Uncle Phil, Will lives is able to experience what it is like to have a parental - and more specifically a paternal figure he never had growing up. And while Uncle Phil may seem cruel to him at times, at the end of the day, he loves Will as another one of his children. His new family in Bel-Air give him the chance for Will to have a new life, and experience the proper childhood he was never able to.