OyChicago blog

A friend-of-a-friend came late to the Golden Globes party I attended this past Sunday. She'd booked a first date for the night and joined us afterwards. Even though many of us at the party didn't know her well, we, of course, all jumped on her for details as soon as she walked in the door— movie stars just weren't holding our attention at that point in the evening. Like many first dates, hers was a bit of a disaster.

She told us— I'm paraphrasing here— that the guy couldn't make conversation, it was awkward and un-fun and only 30 minutes into the date he asked her for plans the next night. Overall, let's just say she couldn't wait to leave and get to the party. We all strongly agreed with her that you should NEVER ask someone for a second date 30 minutes into the first date (especially for the next night!) because it reeks of desperation. This launched us into a conversation about the dos and don'ts of first dates. It was enlightening for this wanna-be matchmaker (who hasn't been on a first date in over half a decade) so I decided to spend part of Monday asking others for their take. The results were fascinating.

I'm not going to lie, there were some differences of opinion, not just between the sexes, and one person I polled responded with, "My advice is don't worry about dos and don'ts," which I also think is a valid point. But while I agree dating games are bad, some general rules are ok— especially for the dating clueless, aka the guy above.  

So compiled below in no particular order are the results of my research. I'm not going to give details and examples for each— there are too many— but I did add my own commentary in italics (couldn't help myself) when I thought it was particularly apropos. Also just because it is listed here doesn't mean I entirely agree with it. Feel free to add your advice and comments at the end.

- Good night kiss is fine, but not required. Obviously nothing more than this is Ok. 
- Play conversation "ping-pong." Take turns talking to each other; make the conversation go back and forth.
- Don't drink too much. Stick to wine and beer or just one hard liquor drink. No shots. 
- Don't come off as desperate.
- Don't dominate the conversation.
- Don't talk politics.
- Do bring something nice like flowers. Maybe save this for a second or third date, but flowers go far. 
- Don't duck on the bill if you suggested the venue. Also don't say, "You can get the next one." Especially when you don't mean it. Don't pretend to offer to pay.
- Have manners and respect for each other. A friend recently went on a four+ hour dinner date with a guy. They bantered all night, made out and she left feeling fantastic. He never called. That's rude. If you go on a date and have a great time but later decide you are not interested, have the courtesy to let someone know. It's called karma folks. 
- Do stick to American cuisine. My friend's date once got sick at an Indian restaurant a la Along Cam Polly, so I have to agree this is a good idea. 
- Don't not ask questions.
- Don't go somewhere too loud that's not conducive to talking.
- Guys should compliment a girl right away. This should go both ways. Who doesn't like a compliment? 
- Do check for allergies.
- Don't pick somewhere super expensive.
- Don't wear too high of heels.
- Do wear skirts and dresses.
- Do get your nails done.
- Don't wear anything too crazy.
- Don't not wear makeup, but don't wear too much makeup.
- If the guy decides to go somewhere that is BYOB, the girl can offer to bring wine/beer. I think this is better for a second or third date. 
- Don't mention exes.
- Don't ask the other person what they are doing the next day a half hour into the date.
- Don't go to Boston market. This is a true story. My friend once had a date at Boston Market. To make matters worse, he didn't even offer to buy her a side of mashed potatoes or a coke. They just loitered in the back of the restaurant. And believe it or not, this guy had the chutzpah to ask her out a second time after this date! 
- Don't complain about your job.
- Do be interested in talking about your job.
- Do meet the girl there.
- Do always open door for girl and lead her to the table.
- Do let the girl order first.
- Don't be rude to the wait staff.
- Do tip well.
- Don't text before a first date. Always call to set up plans. 
- Don't use your cell phone on a first date.