In an earlier post about being the youngest person in the room, someone made a great comment:
What do you suggest to do when it comes down to simple “chatting” or making friends? There seems to be so little in common with people who are 20-30 years your senior. I find that conversations start revolving around things that do not really matter to neither me (the youngest person) nor them. It’s definitely not a secret that if you are good company outside of work and can connect on something in common other than work, it will greatly benefit your business.
In my experience I find that people who are older than I am open up to me more once they see that I am a valuable employee who is interested in excelling and learning. However, making friends on the job never hurt anyone. So here’s how I managed to connect with the older people on my job:

1. Read the paper: Current events (especially local ones) are always spoken about at my job. It helps to be able to join the conversation.

2. Be genuinely interested: Ask questions about their professional life and slowly ask questions about their personal life. For example, “How did you get into this kind of work?” is a question that allows people to draw on professional and personal experiences. Once they share, highlight the value of what they say to you by offering a personal anecdote of how what they say applies to you or ask them to clarify what they say.

3. Be inclusive: Everyone likes lunch—so invite them out when you go grab some food. And if you are doing something new—whether you’re reading a book, taking a trip, or learning a new kind of technology—share! It’s wrong to assume that the generation gap is so large that you won’t find common ground or learn from each other.

4. Don’t be defensive: Every now and then a topic will come up and older employees will say subtly and not so subtly “You don’t know anything about this.” Children and marriage are the biggest culprits. Just excuse yourself from the conversation—you’ll only highlight how young you are. If the conversation is focusing on something you feel comfortable talking about, ask them why they think you can’t contribute and politely join the conversation sharing your experiences.

5. Accept the fact that the relationship may be more of a mentorship: While I understand that people our age have a desire to be friends with everyone, chances are someone who is 20-30 years older than you are is your supervisor thus making the friendship boundary a little difficult to cross. Additionally, think about what you talk about with your closest friends—now think if that would be appropriate for someone older than you. While you may not be buddy-buddy with the oldest people on the job it helps to have a positive working relationship with them that allows them to think highly of you in and out of the office.