’Tis the season for spending time with people you love, and there’s no greater gift to give someone than your time. The problem is when you do spend time with people that matter – whether it’s friends, colleagues, family, your partner, your children – too many spend time the same way you always do, and miss valuable opportunities to create a deep connection with someone.

You ask the same questions, you have the same types of conversations and then you move on in the way that you always do. It’s hard then to create a deep connection with someone because you’re never doing anything differently. You run on the same track in your relationships.

Why do you have the same conversations? Because you’re comfortable with these people and you equate comfort with knowledge of a person. You could be comfortable with your brother, your aunt, your cousin or your child because you spend a lot of time with them. That’s not the same thing as knowledge of a person.

Knowledge of a person is gained through truly opening up that relationship in new ways. Namely, you have to get off the well trodden path to discover somebody. That can be done by bringing a different level of passion to the relationship. It can be done by asking the person a different question.

Perhaps you start with something you admire about the person like, “I really love this thing about you. How do you do that or have you always had that quality?” Maybe you ask about a point in their life in a way you’ve never asked it before or you just try to find out something about who they are today.

Being more vulnerable with someone can open the door to getting to know someone on a deeper level.

For example, they ask you a question and you reveal new information about yourself that you don’t normally reveal. A question as innocuous as “How was your day?” is more often than not answered with the standard, “Not bad; life’s pretty good, blah, blah, blah.” You don’t actually say anything in this way.

Saying something is, “You know what, it’s been a really interesting year. For a few months I actually felt a little bit down because it didn’t seem like things were moving as quickly as I would’ve liked.” Someone is already hearing you in a way they’re not used to – the public relations campaign or the same thing you tell family all the time to avoid any deeper conversations. They’re actually hearing from the real you.

This holiday season, take on this challenge. Focus on a few key moments with the important people in your life that allows you to know them better, thus creating a deep connection with that person.

Never assume that you know someone just because you’re comfortable with them.

This is how you ultimately lose connection with your children when you think you know them. You think you know them because you stay in the same house with them. It’s how you lose connection with your partner when you assume you know everything and you stop trying to learn about him. You start to lose connection because you lose track with who he is today and how he’s evolving and growing. You lose connection with your parents, brothers, sisters, cousins, colleagues and friends.

By having a unique conversation with someone: asking them a different kind of question and revealing different things about yourself than you normally do, you might just find a new moment of connection between you and this person you know so well. Those are the special moments. The moments where you stop seeing someone through the filter of who you think they are.

And, just for a brief moment of authenticity from them or, a moment where they tell you something they haven’t told you before – you see them as independent from you. This human being who is living their own life and having their own troubles, joys and ideas. You get to appreciate them for the complex person they are – not the oversimplified stereotype you have of them in your mind.

So, try to create a deep connection with someone, rather than reciting the norm. I think the greatest form of generosity you can have this holiday season is to truly try and know somebody.

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About The Author

Nicole DiRocco

Nicole DiRocco, founder of Dating With Grace, is devoted to helping executive women have the confidence and skills to attract a healthy, extraordinary loving relationship. A recovering human resources executive, Nicole is a certified dating and relationship coach, blogger, global speaker and chocolate enthusiast. Nicole understands the challenges facing women in the business world and how working in such an environment can influence how women approach dating and relationships. Knowing that it is in being in your feminine grace that will attract the right man, Nicole supports smart, savvy professional women single again after a long relationship or divorce gain the know-how they need to date successfully and attract love from the inside out. Nicole writes for Huffington Post, Dating Advice, Digital Romance, and is featured in Bustle. Follow her on Twitter and Facebook.