Date to Win

by Rabbi Josh Yuter under Date Night,Online Dating,Relationships,Single Life
סוּר מֵרָע, וַעֲשֵׂה-טוֹב
“Turn from evil and do good” Psalms 34:15


I’ve long since forgotten how many dates I’ve been on, but I don’t have that many horrible stories. At worst, most of my dates have been forgettable or what I sometimes describe as, “painless but pointless.” Decent days or nights out with decent people, but either no chemistry or just pronounced feelings of “meh.”

Regardless of how much time one chooses to invest in any person – some people are always willing to give someone a second date, others bail quicker – when we aren’t interested in someone else, a popular confronting us is “what’s wrong with that person?” This is usually more common among matchmakers, some of whom I have encountered tend to take rejections personally (both before and after the date).

Asking “what’s wrong” can be constructive if it helps someone gain greater insight into their wants or needs, or to help friends and matchmakers refine their suggestions. From my own experience, people ask “what’s wrong” more like they ask “why aren’t you married yet?” – as an accusation meant to put others on the defensive for their life choices. The problem is that most of “what’s wrong” isn’t always apparent, in part because there may not be anything actually wrong at all.


Is it the wine or does this just feel “right?”

Here’s where I think a common cliché may be useful. Looking for the absence of a negative would be what I call, “dating not to lose.” According to this attitude, the default status would be that you’d marry the first willing individual who you don’t find particularly objectionable. Depending on your priorities in life, this may be a perfectly valid option and precursor to a long and healthy marriage, provided of course that it’s your decision and not imposed by external (e.g. family, social, economic) pressures.

But for many others, this is wholly insufficient. I’d like to think that people don’t just want to “get married” as much as they want a happy and healthy marriage. While this is never guaranteed (even in the best scenarios), my sense is that the more optimistic people are in dating, the more hopeful they’ll be entering the marriage. This is more along the lines of what I’d call “dating to win,” where you’re not trying to avoid what could be wrong as much as finding someone with whom you feel “right.” In this regard, the mere absence of attraction or chemistry (however you choose to define it) is itself enough of a “flaw,” such that it’s not worth it to pursue it further.

“Dating not to lose” is a surefire way to get stuck in a long-term dissatisfying relationship, one of those where it’s not bad enough to leave… but not good enough to commit. This can certainly be comfortable in the short-term, and you might even convince yourself to get married, though I’d suspect there would be a greater chance for future remorse and resentment.

“Dating to win” is far more difficult. It requires a certain degree of confidence to be unattached rather than be in a relationship for the sake of being in a relationship, or even continuing to go on dates where you’re just not that into someone. But I’d also suggest that the potential rewards are far greater in the long run.

Don’t Let an Opportunity Pass You By

by Tamar Caspi under Date Night,Relationships,Single Life

We all have crazy schedules and many responsibilities. Everyone has a life outside of dating and relationships, and sometimes it is difficult to find time to see someone you like. That’s why you need to take opportunities when they arise.

If the school you teach at has early dismissal before a long weekend, then make a date for the afternoon rather than going home to catch up on sleep. If you can stretch out your lunch hour and sneak back into the office late, then go on a date in the middle of the day when you don’t have to cut it short and rush back. If you have a busy weekend with out of town family, then break away to have a brunch date or a coffee date, or even a walk around town.

Bottom line: If you want to see someone, then make the time to see them.