Lessons Learned from My First Post-divorce Date

It’s not your actual first date, but it feels like it since you have been off the market for so long. You are out of practice. Awkward silences fill the room. The conversation is stilted. The person across the table is not what you expected, and you may wonder if you made a mistake agreeing to go out. Fear not. First date anxiety is common, and this experience rarely results in a love connection. That said, it's good to jump back into the dating pool when you are ready, and it's OK for that first effort not to be the best time of your life. At the very least, date No. 1 will help prepare you for dates 2, 3 and more.

My return to the dating scene was well planned out. I relied on a company called It’s Just Lunch (IJL) to get me going. As the name implies, this matchmaking service is meant to be low pressure. The people who meet are supposed to be reasonably compatible and the event is a lunch—the least threatening and easiest to blow off meal of the day. I had spent over 45 minutes on the phone with Caroline, my IJL matchmaker, answering a long list of questions she asked in order to learn about my personality, and what I was seeking in a potential boyfriend. The intention was for her to set me up with someone who would be a great fit for me. And I really liked the idea of not having any expectations that this event would result in more than just a one time thing.

Then I went on my date.

First of all, my lunch was actually a dinner. Why? He asked for an evening meal, and I realized that I actually didn’t want to carve some time out of my busy daytime schedule to meet some random guy. While your girlfriends may tell you that dinner with a stranger is not the safest route, we did agree to pick a spot by a mall and I drove, so my escape plan was in place if required.

Second, my date didn’t match my criteria. One of the main things I told Caroline was that I like to exercise and hoped to meet a man who was fit and active. However, when I ventured carefully into the restaurant, I spied a gentleman waiting by the hostess station. He didn't look like working out was a priority. That’s when I realized it was smart of IJL to get my money before the date.

After a quick greeting, I sat down for dinner with my unathletic lunch date. The good news was that the experience was more fun than I had anticipated. He was pleasant to talk to, and we mostly spent a lot of time on small talk about where we we grew up, how we got married, and how many children we had. The food was decent, I didn't spill all over my skirt, and the conversation flowed reasonably well. We even laughed a couple times, but, by the end of it, I was eager to go. There was no chemistry—just a pleasant chat. If I met him at a party, I’d probably have had a similar, if shorter, experience and moved on to the next person.

So, what did I learn? A couple of things. I could go on a date, even a mismatched one, and carry on a conversation. Sure, it wasn’t anything special, but this was the first time I had been talking with a man who wasn’t my husband in this context. That there would be no second date actually made it easy to talk. If I had been sitting across from a divorced Brad Pitt on my first date, I would have probably been looking at the menu upside down and spouting gibberish. In terms of getting my confidence back, the mismatch helped. But my incompatible date also provided a valuable lesson. Services like IJL or Match.com are in it for the money, and if they need to hook you up with someone who doesn’t meet your needs, they will do it (and we even learned recently that they might experiment with mismatches on purpose!).

In the end, I didn’t meet my next relationship partner through online dating or by using a service like IJL, but I do have plenty of friends who have found success in taking those routes. But one thing is for sure, whether it is a company, a cousin or a friend that gets you back on the dating scene, it is critical to take that first hesitant, probably unsuccessful step. Your first post-divorce date is about putting yourself out there and regaining confidence. It’s essential to getting your mojo back after a split, especially following a long-term marriage, and is key to thriving.