How Deeply Do We Go?

man with armor


It’s Friday night and you’re at your favorite music venue. It’s intermission and standing beside you is a really attractive man. You want to approach him, but just when you’ve given up, he turns and asks you how you liked the music. And it begins. One thing leads to another as you meander in your conversation, discovering each other’s likes, dislikes, political views and if intermission is long enough, whether you have a problem with his downing 3 martinis.


Down the block from that club the glare of the computer screen housing hundreds of faces stares back. You see a look, great eyes, a Golden Retriever romping with him on the beach and the lead in, “Say something about his photo!”. You know his height, the color of his eyes, astrological sign and that he is a “social drinker” (whatever that means). Hitting that button to reply, you strike it rich. He responds with an invitation to meet for coffee. Plans are made…


You sit in that local coffee shop where people in your neck of the woods always seem to end up when they meet on a dating site. In he walks, looking pretty much like the photo and you’re off! What do you say after the barista calls your name to pick up your iced mocha?


Where do you jump in and how deeply do you go when you first meet someone? The balance is ever so delicate and will often determine whether or not you make plans for that second date.


Picture the layers of our skin. You remember…the dermis, epidermis and the hypodermis and I think it might help. The top “layer” is toughest and protective, the second dermis produces sweat, and the hypodermis is the nuts and bolts, connective and ever-strong constant layer. That’s rather how we are as human beings. When we meet, we have our protective layer in full operation. We sweat because it’s scary and what we really want to do is dive into the deepest layer to ask questions like this:

Are you a crazy person?”

“Am I going to get hurt?”

“What’s wrong with you that you are still single?”


What’s the alternative? “What’s your dog’s name?”, ” How about those Giants?” You can see the dilemma when you meet someone online with only one reason for being there…to find someone. How do you find out more about them in as “natural” a way as is possible? Find something you liked about their profile and ask them to tell you more. Perhaps it’s that they graduated with a degree in law and are now writing poetry. Maybe you love Italy too. Begin where you are, being mindful of assumptions about their past history, wading in beyond the weather forecast but well before asking them to tell you about their divorce. You have to get past the dermis and it’s main function…to protect from pain and injury… before you can really know him. But, if there is an attraction, you’ll have the time and timing to “go deep”.  So, take it easy and enjoy the ride.


Are you tired of being alone? Want to find a special someone to share this amazing chapter of your life? Scared or don’t know where to begin? I can show you the way.

Call me at 510-817-4242 or email me at

We’ll set up a time for a Complimentary Session to find out what it takes to find love…again

Donna Bailey, MS

Coach, Speaker, Writer and Expert in Dating and Relationships for Grown-ups

Donna’s Big RED Chair






  1. Rhoberta Shaler PhD on March 22, 2016 at 7:57 am

    So true, Donna. You also have to trust that your “dermis” knows something and listen. Everything may be wonderful and hormones may be helping. Or, everything may look wonderful, and carefully hiding the truth. You can’t know. Assume the best, yet leave the rose colored glasses at home so you won’t miss any red flags!

    • admin on March 22, 2016 at 8:21 am


      Thanks so much for adding to this with such wisdom. I always tell clients to pay attention and rather than jump to conclusions, go home and write every feeling and observation down, then put it in the drawer until the next date. Then, check back to see if you observed or felt any of those again and to trust, trust, trust that rather than make up a story because you WANT it to be what you want. Thanks for the words of wisdom and caution!

  2. Bev on March 22, 2016 at 9:28 am

    Yes, this is all good but go deeper… How about you share some great questions… Obviously we don’t want to talk about the weather when we first meet but… sometimes its really hard to even know where to begin conversationally. My stumbling block isn’t in the coffee shop btw on a first meet, but rather its more in the area of initiating conversation when you are only at the message stage on the dating site. You know, those first messages. “Hi” doesn’t get anybody very far and we all know when someone only sends you a message with just “Hi” or the ol familiar “how are you today?” questions it tends to either get no response, fizzle out and not go anywhere, especially when you have a person who types one word answers…. So here’s my question Donna, give me your top leading questions to break the ice (in a natural way) when only at the initial message step of trying to get someones attention on one of these sites….

    • admin on March 22, 2016 at 9:42 am

      Good morning, Bev

      I really understand what you are saying about the earlier dilemma of how to say something that will open up a response if the person is interested in you. There is no series of questions because each person you see causes you to stop and email them. Look for what drew you to the person and respond to that if it’s possible. Common interests are great ways to begin, but that can fall flat too unless you say something provocative or interesting enough to ask for a reply. You can use questions to begin as well.

      I think the key is to look at what draws you to him and begin there. Remember that men really respond to positive and affirming statements. We all like that. Sometimes the question is how “intimate” to be. Example: You love his smile. Do you say that? I would suggest that you do if that is what drew you to him. But, you might want to say something in addition. “Beautiful smile and it’s no wonder. That hiking trail would certainly make me smile. What are some trails you love to hike.”

      Hope that helps. It is one of the greatest challenges in beginning dialogue because we simply don’t have context yet. Good luck!!

Leave a Comment