Dear L.O.L.P.:

How do you tell your friend that she shouldn’t try to buy a guy’s love? And how can I help her see her own worth? Poor girl.

– Worthy of Concern 

Dear Worthy:

Your love and concern for your friend really shine through. You see her worth clearly and wish she could see the same. 

Reading your question reminds me of times in my own life when I’ve used my resources – financial, emotional or practical support – to make someone I was crushing on feel like they “needed me.” For years, I found it hard to imagine anyone would simply want me as I was. Perhaps your friend feels similarly – or perhaps not.

Either way, it’s tough to watch someone you care about repeat patterns that, to you, feel unhealthy or misaligned with their goals. If your friend wrote to me, I’d tailor my advice to her. But as her friend, there’s only so much you can say to shift what may be deep-seated patterns of relating, especially when it comes to intimate relationships.

First, I invite you to turn your attention inward and ask yourself: What gets activated in me when I see her behavior?

• Do you feel frustrated or disappointed that she isn’t taking your advice?
• Are you annoyed by supporting her through what feels like a repetitive cycle?
• Do you feel embarrassed about ways you’ve acted similarly in the past?
• Are you angry at the person she’s showering with generosity for allowing this imbalance?

Your “poor girl” comment suggests you might feel sympathy for her, which is natural. But sometimes, sympathy can indicate a disconnect from our own feelings – or even an attempt to distance ourselves from a past version of ourselves. Could there be parts of you, past or present, that resonate with her struggle?

Self-connection is often the first step when we’re upset by someone else’s choices. Consider asking yourself:

• Am I wishing I had more courage or permission to voice my thoughts?
• Do I need more boundaries or distance from hearing about this dynamic?
• Is there a way I can forgive parts of myself that have also questioned my worth?

Take a moment to pause. Place a hand on your heart and ask, What feelings am I holding around this situation? Then listen to what arises. Offering presence and empathy to yourself first can help you approach your friend from a place of clarity and care.

If your friend is open to feedback (always ask first!), one useful phrase I like is: “Do you want empathy or ideas?” This ensures she’s consenting to hear your thoughts. If she’s receptive, focus on empathy first. Reflect what you’ve heard her share, check for understanding and gently explore what she might be feeling. After that, share your perspective. What’s alive in you, any shared feelings and what actions you hope to see her take.

And then let it go. If she’s unable or unwilling to follow your suggestions, that’s okay. If it’s not okay, that may mean you need more space from the dynamic for your own well-being.

Warmly,

 Lady of La Playa

To read more letters for the Lady of La Playa and other writings by Vanessa VerLee, subscribe to VV’s substack at:  www.substack.com/@vanesaverlee.