OyChicago blog

If you're a single 20-something Modern Orthodox Jewish male like me, you are experiencing trying times when it comes to dating. Not only do you need to find someone you're attracted to, have good chemistry with and who laughs at your jokes, you also need to find someone Jewish. And if that wasn't hard enough, that person has to be willing to detach from a cell phone for 25 hours during the weekend.  

Needless to say, the checklist of what you're looking for suddenly makes it seem like finding the right one is impossible.  

Many of us go through cycles where we meet all sorts of girls. Based on my experience and the experience of other Modern Orthodox men I know, I've found there are five types of women who we are most likely to date before we get married.  

Your On-Paper Bashert  

You met through a Jewish dating site or were set up. Either way, she seems perfect for you. Maybe she loves How I Met Your Mother as much as you do, or enjoys a fine scotch on the weekends. When you first start talking to her online, you think she has it all and are jumping up and down to meet her.  

However, you go to meet her and she's now what you're looking for. Maybe there's no chemistry or she's too self-absorbed. Maybe you're too self-absorbed. You want to believe you can make it work with her, that this could be something special. So you convince yourself to go out with her once or twice more, but to your disappointment, there's nothing there.  

The College Girlfriend  

If you were in college, she'd be perfect for you. You feel like you can be yourself around her and the two of you hit it off. The problem is, you two have no future and it's apparent right from the start.  

Maybe she has no direction in life, or tells you she's "not looking for something serious." Maybe she always consults her parents before making any sort of decision, such as whether or not to go on vacation with you. Or maybe it's you -- you're not sure what you want just yet. You just don't see eye-to-eye with her on what you want your future to look like.  

These girls make great friends and are fun to hang out with, but simply aren't for you in the long term.  

The One You Regret  

Perhaps you made out with her at a Purim party or spent all your time with her over a Shabbaton. Either way, you quickly realize this isn't college and you need to be a gentleman. You go on a date or two with her only to realize that your conversations are as exciting as watching paint dry.  

Sometimes, this girl is on the same page as you. Sometimes, one of you has to be the one to  break it off, which is rough, but cooler heads eventually prevail and it becomes an experience you both let go.  

The Girl Who Makes You Swear Off Dating  

This is the one that hurts. Maybe it was her fault: she stood you up, strung you along or held her past negative dating experiences against you to the point that you felt like you couldn't win. Or maybe she revealed something about you that you that was tough to hear. Either way, you question yourself and even question dating period.  

The thing to remember is that while meeting someone like this can hinder your willingness to date, these are the exception more than the norm. And as the saying goes, "What doesn't kill you makes you stronger." At the end of the day, this girl is what's going to make you truly cherish your bashert.  

The Crappy Timing Girl  

This one causes a different kind of pain. You meet at the most unexpected time, usually just before one of you moves away or makes a big life change. Or you meet and it turns out she's just in town for the week visiting friends. The second you meet her, you think she could really be the one. The problem: this relationship has either no starting point or a definite ending point and there's no way around it.  

When you say goodbye, there's not an ounce of resentment in your body and no bad feelings: there is a hope that at some point you reconnect and make it work even though the odds are stacked against you.  

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Whether you've dated all five of these women, or only identify with a couple, remember there is a reason they came into your life. I believe each type ultimately teaches us about ourselves and we are better off for meeting them, even if they're not Mrs. Right. Often, your encounters with each of them provide you with greater clarity and perspective for when you finally find Mrs. Right.