How To Online Date In Chicago – 8 Tips From Our Expert!


Photo: Rex USA

We're a gigantic city of young professionals. Finding just one person to date can be like looking for hay in a haystack. There's got to be an efficient way to meet someone you're going to spark with. Oh, right. There's an internet for that. Meet Melissa Malka, a dating coach living, working, and yes actually dating in Chicago. Her company, Just A Little Black Card, is a trusty resource for anyone who needs a little dating pep talk and she's here to dish out advice for anyone about to leap into the online dating world. We strongly recommend listening to her expert tips if you're looking to build your profile or communicate with other online singletons. Learn her do's and don'ts, and start your online dating adventure on the highest note possible. If you're already well-versed in web-based flirting, leave your pointers in our comments section. Share the love!
1. Pics, please!
Sometimes I despise that this is important enough to actually be the first item on the list, but I’m not going to lie to you, pictures matter. We live in an info-driven age (hello, Google) and more often than not, attraction is figured out through physical appearance. So not only do you need a picture up on your profile, you need a certain type of picture. I live by the no extreme close-ups, crops, or cups rule. That means your picture should include at least half of your body in it (the top half, preferably!), shouldn’t be one of those pictures where it looks like you just cropped your ex-boyfriend out (I know you’ve seen this before!) and shouldn’t be of you holding an adult drink. At minimum, have three photos up. Make it a close up, a full-body shot, and a picture of you doing something you love. My online dating profile has a picture of me drinking coffee from a really cool mug. Total conversation starter.
2. Write what’s right!
If you lie or, rather, embellish in your profile, you’re going to have a hard time wriggling yourself out of that mess when you end up liking the guy you go on a date with. A profile shouldn’t be too long, so don’t give a full history of yourself. For your profile’s written content, follow the about me, about you, about us rule. In other words, write a bit about you, a bit about the person you’re looking for, and a bit about the kind of relationship you’d imagine yourself happy in.
3. Respond politely, no matter what
If there’s anything I’ve learned from online dating in Chicago, it’s that you’re inevitably going to run into many someones that you’d spoken to via online dating site. The city is a smaller place than you’d think and the last thing you want to have happen to you is to be chatting up a cutie at a party only to have his friend tell him that you were a jerk online. It happens. It’s happened to me, a lot, before I learned my lesson. You’re going to receive a lot of messages when you join a site (you saucy minx!) and half of them might be three word messages like “what up babe” and those are ok to ignore. But, the guys who take the time to write you something nice deserve a response, always, even if you’re not interested. Something polite, then move on. Not only does this ensure that you avoid awkward moments in the future, some sites will actually calculate your rate of response and display that publicly. Not responding means a lower rating, means some guys might not even bother writing to you.
4. Who messages who?
This is a question I get asked a lot. One of the issues with online dating is that we can bravely hide behind our computer screens and message a bunch of guys when in real life, we’d never dare approach a guy at a bar. Its as if our initiative gives an inaccurate first impression to the guy we’re messaging. With that said, I think its 100% ok to message a guy first because he might not even have seen your profile but let him take the lead after that. If he’s interested in you, his male-pursuer light will go on and if it doesn’t, move on. You don’t want to be the one chasing him, trust me.
5. Keep it moving forward
One of the biggest issues with online dating is falling into the “online relationship” rut where you talk to the guy, connect with the guy, and never actually end up meeting in person. A few exchanged emails, one phone call (that he dials) and an invitation to go out are all you need to convert your virtual relationship to a real life one. So remember, email, phone, date.
6. No IM’ing!
IM is one of the biggest online “relationship killers” and that’s because you never end up taking the relationship offline. You email back and forth for weeks, then switch to IM, and never actually get on the phone to set up a date. I’ve got rules for this too: no giving out your online chat name. This just makes it way too easy to fall into that rut where you’re “getting to know each other online” but never end up going out. By they way, I’m not referring to the initial IM conversation you might have on the actual dating site, but after that.
7. Play it safe
Regardless of whether you’re in Chicago or not, be savvy about your online dating. There’s a reason I brought up talking on the phone in #5, not only is it a good way to gauge your chemistry, its also a way to ensure that this person is really who they say they are. And, of course, never give out your address (I rarely even give out my “neighborhood” and will give more a general region) and meet in a public place for the first time. Finally, tell one of your friends where you’re going and at what time they can expect you to check in with them. I call this the kidnapping call as in “if I don’t call you by 10, I’ve been kidnapped.”
8. Have the talk
There’s a specific DTR (define the relationship talk) that comes with online dating and that is the talk about taking down your online dating profiles. You’ve met the guy, you’ve gone on a few dates, you’re into each other, now what? Before I tell you how to approach this, let me first explain the issue: online dating is the window-shopping equivalent of available singles and even when you can’t spend any more money, it can be really hard to stop looking. It’s reassuring to know that there are more people out there, for both men and women. But, if you’ve gone on more than 3 or 4 dates and you dig each other, it’s time to have the talk and this is one you’re going to have to bring up and gauge his reaction. If he’s reluctant to sign off, that might not be a good sign.

More from Chicago

R29 Original Series