OyChicago blog

I recently picked up a new hobby: matchmaking.  I’m not exactly sure when I became obsessed with fixing people up, but with each success I’ve gotten more confident in my skills and well, no one I’ve set up has yelled at me…yet.  I’ve got one marriage and a live-in couple under my belt— I hit a high this past weekend when a couple I introduced became official and the two friends who I knew would have chemistry took a liking to each other.

Getting involved in people’s romantic lives, is a risky endeavor, but it’s also afforded me a unique glimpse into the world of dating for both men and woman in Chicago…and again since so far no one has yelled at me, I’ll continue to do it.  I admit I’ve always been a bit of a busy body— back in college I started dispensing my dating rules and relationship advice to my friends.

Though I do dream of being the Patti Stanger of Chicago (with a little less snark and a lot more affordability), I’m not ready to quit my day job.  However, a friend recently suggested that I start sharing my advice and stories with more than just my own network— so Oy!sters, welcome to my inaugural relationship blog post.

Disclaimer- I admit I’m old fashioned, but when it comes to millennial dating, I really think everyone should be.  When it’s common for guys and girls to meet after midnight, in a bar, on a Saturday night, five drinks deep, it seems like a no brainer we should all be a little bit more protective of our hearts these days.  But I’m sorry ahead of time if I offend anyone— I know being single is tough and there’s no magic way to find a soul mate.

So, here are my dating dos and don’ts:

Don’t hook up with someone the night you meet.  This seems so obvious, but I hear stories all the time of girls in their mid-to-late 20’s who are surprised and disappointed when they spend the night with a guy they just met in a bar and he never calls.  I realize spending the night doesn’t necessarily mean having sex, but just sleeping in someone’s bed is too intimate too fast.  And frankly, any guy who wants you to come home with him the night you meet is only hoping for one thing…

First dates on weekdays are fine.  I’m a firm believer in going out on actual dates.  A date doesn’t have to be fancy dinner downtown, and the guy doesn’t always have to pick up the check (just on the first one), but the effort that goes into planning an actual date and asking someone out on a date can go a long way.  By the third or fourth date, he should be asking you out on weekends, too.  After a month of dating, if the girl you’re seeing still refuses to make plans on the weekends, then she’s just not that interested in you and it is time to move on.

Run away from the guy or girl who only wants to “meet up in a bar.”  On the other hand, if the guy you like only wants to see you on the weekends, in a bar, when he is out with friends, move on.  He’s just looking for a hook up.

Use texting and social media sparingly.  I love texting and social media as much as the average person (it is part of my profession), but there is a time and a place to use social media.  It’s fine to text the girl you like occasionally, but make sure you call her once in awhile, too.  This goes the same way for girls.  Guys shouldn’t be the only ones picking up the phone.  The biggest complaint I’ve heard from my male friends about the females they are dating is that they never initiate and they never call.  We expect guys to make efforts to woo us and it should go both ways.

Make that online dating profile.  I don’t care if you use JDate, Match.com, or eHarmony, just make one!  You have nothing to lose and it is a great way to expand your dating pool.  I know people worry about how they will look, but really everyone is doing it these days.  And yes, there may be some creepy people using online dating sites, but there are creepy people hanging out in bars, too.  Just avoid them.

Make time for that profile.  A lot of people tell me the reason they don’t want to use online dating sites is because it takes up too much of their time.  My response, “relationships take work and if you don’t have time to invest in one, you’re probably better off single, at least temporarily.”  I’m not saying you have to spend hours working on your profile or winking at girls, but put as much effort into it as you would want your potential mate to put into you.  Creating a profile can be daunting— take it slow and don’t be afraid to ask a friend to help look it over.  A tip for creating a great online dating profile— try to end the “about you” section with something that elicits a response.  For example, you could do three truths and a lie about yourself and ask potential suitors to guess which one is false.

Stop trying so hard.  Know when to go on a dating detox. After a break up, even if it’s only for a week, you need to take a break from the dating scene to focus on yourself and your happiness.  If you’re going out every Thursday, Friday and Saturday night searching for your next boyfriend, ask yourself if it’s time to take a dating detox.  If you’re juggling three girls, none of whom you are really interested in, it might be time to take a dating detox.  We can all smell desperation— no one wants to date a girl who is hunting for a husband.

Always accept a first AND second date.  This one can be hard at times, but try to always accept a first date.  It’s good karma and you never know what might come of it.  Also, many of my friends complain to me that they don’t get asked out anymore, so when you get that elusive date offer, take it!  More importantly, go on that second date!  People are nervous on first dates and might not make the best impression.  Don’t tell me you’re not interested in a second date because the girl was wearing an unflattering shirt or the guy picked a bad restaurant.  Now, if on the third date, his shoes are still awful, then you are free to move on to the next guy.  This second date rule goes both ways— you might have had a great first date and have already started fantasizing about your dream wedding, but don’t get ahead of yourself.  Second dates determine real chemistry.  You might have had great conversation on the first date, but is there anything left to talk about?

That’s all I have for now, but I’ll be back next month with more.  In the meantime, I’d love to hear some of your dating rules.  Also, I’m always looking to set people up and expand my own network, so if you’re interested, drop me an email at cherylannjacobs@gmail.com or leave a comment below.  Happy dating!