The mere sound of Jamie's voice made my heart thump wildly. He said he'd like nothing more than to meet me but admitted he still felt scared. "You might not be attracted to me."In hindsight, I should have cut and run right then.But I wanted badly to connect with someone, and the truth is, I shared some of his fears. He said he'd joined determined to overcome his intimacy fears but hadn't been moved by any of the women he'd met. I want to hear your voice."He called me that night, and was even smarter and funnier on the phone. "Ever since my father died, I've been terrified to get too close to anyone..." The e-mail was long and apologetic, full of searing self-criticism and shamefaced confessions. We knew a couple who broke up after living together. We discussed moving in together when my lease is up in October, but now I know he’s not ready. I tell him that he can still have that if we’re living together, but he’s still not sure when he’ll be ready. He feels really strongly about living with me and equates it to marriage.I remember the first e-mail I received from Jamie; it wasn't exactly poetic. Looking back, it's hard to believe what that simple line would lead to. At the time, I was nearing 30 and working as a secretary at a big investment bank in New York City—not exactly the fulfillment of a lifelong dream. So I checked out his profile immediately, but wrote him off just as fast—he lived in the Midwest and, more importantly, hadn't posted a photo. He persisted and e-mailed a few snapshots, along with a note. But it was at night that our talks really picked up steam. Paul's reaction mirrored that of my friends, sisters, and parents, so I clammed up. I was working in a dead-end job, watching my friends get married one by one, and kissing my 20s good-bye, having apparently missed the "Saturn Return," that astrologically significant period that occurs between the ages of 28 and 30 and is supposed to be marked by accomplishment, power, and prestige.Turns out he was reasonably cute, and really funny. This went on for a couple of weeks until I said, "So, do you want to come to New York for a date? I canceled evening plans more than once just so I could go home, change into my pajamas, and curl up in bed with the phone. At some point, I again broached the subject of meeting with Jamie.
Then he'd found me—a woman he might want to have a real relationship with. "Please," he begged, "give me another chance." I hesitated. I'd planned to merely dip my toe in the water, but instead, I cannonballed right in.
I’d ask the same question about your weekend trip ambitions: Have you ever taken the lead?
Have you told him there’s some place you’d like to go? If money is an issue (and it always is), have you suggested an affordable trip to a nearby Airbnb? Have you ever thought about just booking a spot for two nights and surprising him? (If you’re waiting for him to read your mind, I hate to break it to you but it’s not going to happen, ever.) Basically, I just want to remind you that these aren’t end-of-world issues.
At least that’s what I told my now husband on year five of our dating relationship.
I was sure he was the one, I felt ready, and I knew he loved me back, so why not move ahead?