Long-term relationship in your 20s = zero dating experience. Imagine our surprise when one day a guy we’d been introduced to in a semi-professional setting flirted with us. Over email. Several back-and-forths ensued before he asked us out for coffee. We accepted.
Met at a coffee shop one afternoon, just a quick break from work. He arrived wearing pleated Dockers, a navy blue sweater vest with a regular blue button up underneath and a royal blue T-shirt poking through. Now, lest you think we’re shallow – some guys can rock the sweater vest. Dads. J. Crew models and those arty-hipster guys. Our Sweater Vest was too dad-ish. And all those different blues...not sexy.
But, the date progressed. Conversation was fine but not memorable. After about a half hour we needed to get back to work and said so. Parting in front of the coffee shop Sweater Vest said “This was fun, we should do it again soon.” And we, not being very good at rejection in general, but certainly not on our first-date said “Talk soon.”
Ten minutes later and just back at work, our phone rings. Should we answer?
“Hi, it’s Sweater Vest.”
“I just wanted to say that I had a great time and we should do it again soon.”
(Didn’t we just have this conversation?)
“Uh, yeah. Sure. Talk to you later.”
Ten minutes later – a new email. From Sweater Vest. “Hi, I’m sorry if I freaked you out when I called earlier. Didn’t mean to. Had a good time though and we should do it again sometime.”
Wow. Don’t respond for awhile but, being the nice people we are, we decide that everyone makes an ass of themselves when dating and we don't want him to be sitting at his desk agonizing.
Email back – “No big deal. It was nice meeting you. Have a good night.”
A few days later, email from Sweater Vest: “Hi, how are you? Interested in getting together for a drink?”
No Sweater Vest, we are not. “Actually, we aren’t really interested in dating right now. Nice to meet you though. See you around.” (OK, we admit it, we need to work on our directness but…we don’t like to hurt people’s feelings.)
The response: “I just want to be friends. So, how about that drink?”
Friends? Yeah right. We don’t respond.
Two weeks later – another email from our favorite Sweater Vest. “Hi, haven’t heard from you in awhile. Did I do something wrong? Are you mad at me?”
This is too much. Sometimes it takes us more than two weeks to respond to people we like, people we have relationships with, people who aren’t complete disasters. We let him sweat this one out.