To call, or not to call

I’m 33 years old, have had two intimate relationships, but only recently had my first real date. Somehow my emotional walls dropped afterward. We’ve had two dates now and I’m ready to let her know I like her. It’s probably clear—I’ve told her she’s cute and went to dinner at the last minute at her invitation. But I feel inadequate because of my finances. I live with relatives and work part-time while building my artistic career. From what I can tell, she’s not one to prioritize money, thankfully. I want to let her know I’m attracted, but don’t want to be pushy or clingy (huge turnoffs for me). I’m mature enough to understand if it’s not going to happen. She’s busy with work so I’m trying not to contact her much. But I don’t want what we have to go sour. How do I go forward in the most effective, healthy way possible?

Congratulations, you’re doing it—your newly opened heart senses romantic possibilities, and yet you’ve managed to keep your brain engaged and strategizing. Don’t worry about money (more on that later), focus on the wonderful qualities you have to offer: thoughtfulness, intelligence, creativity, attraction, passion for a dream and readiness to commit. I also want you to rethink your hesitation to contact her. While I appreciate your consideration of her schedule, you are losing opportunities to connect. So call her more often just to ask about her day. If she’s busy building a career, she might appreciate having someone to rely on. You don’t have to understand her industry, just listen for the moments in her stories where she needs encouragement or where she is missing a deeper truth. Ask her how she feels about the situations she shares with you. Be the man who believes in her. And, if you reach out and she doesn’t respond, don’t take it personally. Keep reaching out.

Let’s talk about wealth. There’s financial currency—dollars we earn, spend or bank—and we all need cash to pay our way on the planet. But there’s also social currency—our circle of friends, neighbors and community members whose kindness, support and appreciation enriches our lives (and vice versa). Your network of personal relationships adds to your net worth. If you want to be free of feeling inadequate about your finances, value your social wealth.

One last thing, there’s a weird excuse that women in their 20s and 30s use to stop seeing a really great guy. It’s this: “He liked me too much.” Strange, right? Sometimes the woman is so insecure she can’t accept that a guy could be so into her. Other times, the guy has really big romantic feelings that have nothing to do with the woman he’s projected those feelings on. (Think of Shakespeare’s Romeo. At first, Romeo is obsessed with Rosaline. She wasn’t interested, so he transferred his feelings to Juliet.) Don’t let this information scare you. Just be aware: two dates is enough to be crushing on each other, but you need a lot more time to see if what you have is love.