One sip at a time

What is the right way to ask out a coworker? She is a wine salesman and I am a wine buyer. I’ve had this job for five years and have never mixed work with my personal life. I am at a position of power since I decide if I buy what she is selling or not. I would like to get to know her more and see where it goes. What is your advice?

Approach the relationship like you would a fine cabernet: one sip at a time. Don’t overwhelm her with romance. Focus on establishing a friendship first. Get off-site with outings that relate to your shared interest in wines, but keep the conversation personal. Ask her questions about herself and open your heart to reveal the truth about who you are.

Need help brainstorming questions? Read The New York Times article, “The 36 Questions That Lead to Love.” It’s a guide to the kinds of conversations that build emotional intimacy. These questions work equally well for platonic friendships or for relationships that hope to develop into a romantic commitment. In general, people who opt out of these questions either aren’t capable of emotional intimacy or don’t want intimacy with the person inquiring.

Be certain to use the questions skillfully. Notice the intentional progression of the questions on this list and stick to it. Don’t fire questions like an investigative reporter, either. Be chill. After all, this is about love, right? One or two questions per outing is probably enough. You can even share the questions with your crush as a way to let her in to your desire to understand, appreciate and connect with her.

If your dates don’t lead to a commitment, be mature about it. Return to interacting with her as a professional. Reserve your disappointment for a conversation with a trusted friend or life coach. Don’t be a downer, and don’t try to blame her for your feelings when interacting with her at work. My book, When Your Heart Breaks, It’s Opening to Love: Healing and finding love after an affair, heartbreak, or divorce, is one resource that can help.

Thanks for the column on social media platforms (“How to be creepy,” February 22). One confusing thing about Bumble is that many women include their Instagram address in their profiles. I was unclear on the protocol for this since Bumble requires women to reach out first. Even so, your column helped me understand the “creep factor.” Any thoughts about those Instagram handles?

I’ve noticed Instagram handles included occasionally in men’s profiles, too. When I type those handles into Instagram (I’m loathe to click on links), the accounts are inevitably related to a business or service. I’ve seen multilevel marketing schemes, promotional accounts for massage, tatts and photography services, fee-based social clubs for singles and even international tours. And, yes, I’ve seen links to Instagram accounts filled with seductive photos of a guy who appears to be selling his personal escort services using a dating profile as the entry to his sales funnel. Hey, there’s a schemer born every minute. Don’t be a target.