attends the Fashion Trust US Awards at Goya Studios on March 21, 2023 in Los Angeles, California.
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Here's How to Navigate a Significant Age Difference in a Relationship

Young dude doesn't want to be crude or lewd, just set the mood with a mature woman of great magnitude 

The sad truth is, we're probably a mere few decades away from seeing the storyline of I, Robot play out IRL. But until the android apocalypse, we might as well make the best of artificial intelligence. So here it is: LEVEL's new advice column, We Asked a Bot, the place where your pressing concerns and queries are treated with a tenderness and care befitting of a machine learning algorithm.

Dear Level, 

About a year ago, my work mentor introduced me to one of his friends, a very attractive woman that he thought might be able to help me with a business idea I had. The business idea fizzled the new relationship did not. It became flirtatious immediately. We were both drawn to each other right away and it didn't take long for things to get physical.

Related: Office Relationships Are Too Damn Messy

The relationship seemed like a fling at first and was very casual, but in the last few months we've been making more of an effort to see each other and we've taken a few trips together. I like this woman a lot. She's funny, sexy, knows who she is, and is very successful in her career. I'm flattered that she wants to spend time with me. Which brings me to my problem… I'm not sure if she takes me seriously. I don't want to be her boy toy, and she doesn't talk down to me or treat me like one, but I worry that our age difference (I'm 30, she's 49) might be hard to overcome. What should I know about how to treat an older woman and what can I do to make sure she doesn't think I'm too immature to be with her long-term?

—Old Enough in Houston

<We asked Perplexity, a search engine that's not too different from ChatGPT, to answer this question in the voice of someone with deep knowledge of mature women. Let's see how Perplexity did:>

Dear Old Enough in Houston,

It's clear that you care deeply about this woman and want to ensure that she takes you seriously. The age difference between you two can present challenges, but it doesn't have to be a barrier to a meaningful relationship. Here are some tips to consider:

  1. Show Genuine Interest in Her Stories: When you're chatting with an older woman, really listen to what she's saying. Ask questions that show you're paying attention. This shows that you value her experiences and find her life journey intriguing.
  2. Respect Her Experience: An older woman has a wealth of experience – and that’s something to respect, not undermine. Acknowledge her wisdom and life experiences. If she gives you advice or shares her insights, take it seriously.
  3. Keep Things Light and Positive: Maintain an optimistic outlook and handle serious topics with sensitivity and understanding. Share your passions and encourage her to share hers. Keeping things positive creates a space where both of you feel comfortable and uplifted.
  4. Embrace a Sense of Humor: Inject humor into your conversations. It doesn’t have to be stand-up. Everyone loves a good laugh, and it can help create a strong connection.
  5. Be Confident, But Respectful: Confidence is attractive, but it's important to find the right balance. Listen as much as you talk, and value her opinions. It’s about finding that sweet spot where you’re both comfortable and enjoying the interaction.

By approaching the relationship with respect, genuine interest, and a positive outlook, you can show her that you are mature and serious about being with her long-term. Remember, every individual is unique, so it's essential to have open and honest conversations with her about your expectations and to listen to her perspective.

Best of luck!


<We really like the suggestion of showing lots of respect and listening (although that would apply to women of any age). Except for the part about "respect her experience," it didn't seem like Perplexity really gave much insight about the age difference and how to address it. We asked specifically about that, posing the question, "What should Old Enough in Houston do to address the age difference? What are some talking points for a discussion about it?" Perplexity responded:>

When addressing the age difference with the woman you're seeing, it's important to have open and honest conversations about your feelings and expectations. Here are some talking points to consider:

  1. Express Your Feelings: Share with her how much you value the relationship and what you admire about her. Be honest about your concerns regarding the age difference and the importance of being taken seriously.
  2. Discuss Long-Term Goals: Talk about your long-term aspirations and see if they align. Understanding each other's goals can help determine if the age difference is a significant factor in the relationship.
  3. Seek Her Perspective: Encourage her to share her thoughts on the age difference and how it may impact the relationship. Understanding her viewpoint is crucial in navigating this discussion.
  4. Emphasize Mutual Respect: Highlight the importance of mutual respect in the relationship. Ensure her that you are committed to treating her with the respect she deserves, regardless of age.
  5. Explore Shared Interests and Values: Focus on the common ground you share, such as shared interests, values, and emotional connection. These factors can be more important than age alone in a relationship.

By approaching the conversation with sensitivity and respect, you can address the age difference in a constructive manner and gain a better understanding of each other's perspectives.

<More respect! That's solid advice, and we like the idea of setting some parameters about whether the relationship is long-term or short-term in her mind. On the other hand, one piece of advice we would give: Read the room. The woman may not want to have her age (and the age difference) brought up all the time. If she seems uncomfortable discussing it or gets tired of it coming up again and again, know when to back off and just enjoy what you have without overthinking it (or overtalking) too much. Good luck, and let us know how things play out, player! Until next time!>

LEVEL consulted for the aforementioned text. Need advice, insight, or just want to troll a chatbot? Hit us up with your questions at We'll feed it to the robots and see what it spits back out. (Disclaimer: YMMV!)