OyChicago articles

In this season of reflection, as we look back on the past and look forward to a fresh start in the Jewish New Year, Cindy Sher offers first date tips to guys. Then, Jewish Chicago single guy David Cohen responds with a few dos and don’ts of his own for the ladies.

First date tips for men

By Cindy Sher

Over the course of my single years, in between relationships, I’ve gone on a lot of first dates. And trust me, first dates aren’t always as magical as they sound to people who don’t go on a lot of them.

If you met the man or woman of your dreams on your first and only first date—do people like you really exist?—you may not relate to my adventures in first dating.

For instance, my dear married friends with babies can’t quite relate. They lovingly try to talk up my pending dates with potential suitors; maybe some of these “mom” friends are even envious, living vicariously through me and my singledom.

Through my dating years, I’ve met many lovely Jewish men—mensches. Even though it didn’t work out with us, I know they’ll make wonderful husbands and fathers some day, and I wish these men many blessings.

But my column isn’t directed at them.

What follows is advice to some of the other men I’ve gone on first dates with, who weren’t, shall we say, my perfect match. In fact, we never went out again.

Now, maybe there are guys out there who didn’t love me so much on our first date either. And maybe, one day, I’ll even read about some of my own blunders on their blogs and Facebook walls. But for today, you’ll have to settle for “Cindy’s dating wisdom.”

Finding a date 
In order to even get to the date, there’s often an Internet dating site, like JDate, to conquer first. Beware of the following steps in creating your dating profile:

Don’t tell me you’re looking for a woman who’s just as comfortable in sweats or a bathrobe as she is in a ball gown and high heels. The only way that would ever happen is if a designer comes out with a terrycloth line of strapless dresses and Nike heels.

Don’t write that you’re looking for a woman who cares about “an extremely healthy lifestyle.” We know that’s code for you want to date a “size 0.” Chances are you’re not really all that concerned about your future date’s iron deficiency or red blood cell count.

Do use good judgment in choosing your accompanying photo. What’s with the woman posing next to you that looks like your girlfriend? She’s cute, she’s about your age so she’s clearly not your mom or grandma, and you guys look like you’re having a ball together. Why not just date her? Or maybe she’s your sister?

The first date
Mazel tov! You’ve made it to the first date. What follows are first-date dos and don’ts, each nugget of advice based on my array of my real-life first dates.

Do get a little excited about your life; if you’re not, fake it. One man told me within 30 seconds of meeting him that “there is nothing interesting” about him and he leads “a really boring life.” Now I ask you, does that make me want to jump at the chance to share the rest of the date, let alone a lifetime, with Mr. Boring?

Do be kind to the waiter or waitress. Nothing reveals your character more than how you treat your server. Striking up a conversation with him/her earns extra brownie points with me.

Don’t try to sneak into a movie on a first date. Seriously, this actually happened. I realize that the cost of our two tickets will not make the difference of whether or not the Cineplex conglomerate or Adam Sandler go broke, but it might make the difference of whether or not you and I go out again.

Do offer to pay for my $2.43 tall hot cocoa with whipped cream at Starbucks—if you asked me out. This isn’t about you shelling out a lot of money. I don’t care about going to a fancy steakhouse for dinner and I will gladly pay on future dates. But deliberating over which one of us owes the extra three pennies in front of the Starbucks barista isn’t flirtatious, romantic, or sexy.

Don’t tell me tacky jokes about cheap Jews or Jewish American Princesses. They’re not funny.

Do, on the other hand, feel free to make me laugh. And whatever you do, don’t take yourself too seriously. We’re on a first date and first dates are, by their very nature, awkward and funny.
 
Then again, what do I know? I’m still single. Maybe you should talk to one of my “mom” friends—or better yet, her husband. He made it to the second date.

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First date tips for women

By David Cohen

Finding a date
Don’t have your only picture be one that’s taken from far away or with sunglasses on. Yes, you do look great in your big ol’ Nicole Richie shades but I really just want to see what your face looks like. You're not in the witness protection program; you're just slightly embarrassed about being on JDate. It’s 2009; Internet dating is now mainstream. There is no shame. (Well, maybe a little shame.)

Don't describe yourself by using whimsical, sensory, observations like, "I love the smell of leather" or "Fresh snowflakes on my window ledge make me happy.” This isn't a poetry contest. Stick to describing your personality, your interests, and your priorities in life.
 
Do include a picture that shows me your figure. I know, I know, “men are so shallow.” Guilty. It has to do with evolution, but I’m looking for my soul mate. Before I contact you, I need to know if we might have chemistry together, or I’m likely to pass on your profile. If it makes you feel better, I have my skinny little chicken legs out there on the Internet for all the world to see.

Do give me your full attention on our first phone call. There’s nothing worse than trying to have a meaningful conversation with someone distracted while she’s in the check-out line at Jewel-Osco. You’re not making a good first impression on me or that cashier in front of you. Just ask to call me back when you’re home, after you’ve put away your soy milk.

The first date
Don't dominate the conversation. It's a known fact that women talk more than men so I expect this on a certain level. Let me get a few words in too. You’ll have plenty of opportunities to talk my ear off when we’re in an exclusive relationship.

Do reach for your purse when the check comes. I love this move even if I sense you’re bluffing me. I understand I’m expected to pay for the date and I’m happy to do it but I’m still charmed by the gesture if a woman offers to pay her share of the tab. I’ll always decline it. If you’re not into this tactic, no problem. But without a doubt, thank me at the end of the date for the drinks and/or dinner.
 
Do flirt with me if you like me and want me to ask you out again. Make it super obvious. If we made it to a first date, then your odds of a second date just went up significantly. The odds decrease, though, if I’ve gotten no sense that you’ve enjoyed my company. Tell me you love these ill-fitting pants that I got at T.J. Maxx. Or, reach for my hands and tell me how great my rough cuticles are. Give me something to go on. Fidgeting with your hair and good eye contact just isn’t cutting it.
 
Don't contact me after the first date no matter what your girlfriends say. If you flirted with me, then you'll hear from me—unless I’m just not that into you. Sending me an email, text, or voicemail, even just to thank me for the date, makes it too easy for me. I want to feel like I had to work at it…a little.

David Cohen currently resides in Chicago's Lakeview neighborhood. He agrees with Mom, friends, co-workers, and you that he is way too picky.