Adventures in Dating in Chicago

Hey,

So everyone is hitting me up on facebook, myspace, email, all confounded because they have no idea what to do as far as a date. In the previous blog, where you can skim here, I broke down the different types of dates, so that you don't try a first date activity on a romantic date. As I've also said, I live in Chicago, so some of my ideas will be Chicago based, but I will try to make them as universal as possible. With that, here are some of my ideas with the category it can fall into. If you try them, I'm pretty sure they'll succeed and get you serious cool points. 

The idea of a date is to let someone into your head a little. If you show them the basic dinner/movie combo, while it works, it's boring. We have all done the dinner/movie date. There are ways to tweak that idea a little, a lot and eliminate it entirely. Here are some suggestions:

Instead of going to dinner, why not learn to cook a meal together? Places like Parties that Cook have options that give couples a chance to cook a menu from appetizer to dessert. However, you should not do this as a first date, because you need to know the person is interested in cooking. Also, it can be a little pricey, but there are cheaper alternatives. They also offer singles events, so you might learn a few recipes, then find a date there to share it with. This kind of date is perfect for second or third dates, because it allows you to get to know the other person and the activity allows for many goofy awkward moments, giving you both things to laugh about later. Google "date night cooking class (your city)" to find plenty of options, some that just teach one part of a meal, or the whole thing. It'll depend on you and your budget. Some are free, some charge small fees for the materials. If you google "cooking class (your city)" you can find less expensive options.

After cooking a meal and sharing it, why not park your car (or take the bus/train) in a neighborhood like Lincoln Park or Oak Park and walk around. All those calories will make you feel stuffed, and walking will get that bloated feeling out of you. I recommend anywhere full of interesting shops, people and cafes. After walking around for a while, you can get a drink (whether it is coffee or a shot of Patron) at any place that looks interesting. Open yourself up...the possibilities are endless. 

For example, a city like NY, where parking is out of control, take the subway to the Lower East Side and try coffee at the Nuyorican Poets Cafe, one of my favorite hangouts when I'm in town. There's always someone on the mic with spoken word, and it is full of various types of folk, the yuppie, the internet blogger, the student, the hippie, the weedhead, the 'ignit' spectator, the next Miguel Pinero. (if you don't know who that is, look him up here). 

Google "poetry cafe (your city)" to find a place near you that offers up poetry nights. You might go a step further and get on the microphone yourself...but I say go for it if you're brave. Don't do it just to impress your date, if its not genuine it'll more than likely backfire. This also can be done as an independent outing and even a first date if you know the other person likes poetry. However, do a little research and make sure the place is not so loud that you can't hear the other person if they say something. The last thing you want is to not talk to the person, especially on the first date.

Another good date idea is to take your date to a local museum, art exhibit, or aquarium. Chicago, and many other main cities have these. Chicago, and probably other cities, offers something called the CitiPass. The great thing about this CitiPass is that it is valid for nine days, offers admissions to five of the city's great tourist and museum attractions and is cheaper than trying to buy each ticket seperately. Read more about  and even buy the CitiPass here. This can be a two or three day date, and will allow you both to learn more about the culture of the city and while it is 59 dollars, it is less expensive than trying to pay for all those places individually. The Pass also has discounts and maps to restaurants, shopping and other locations that can allow you to see the city with fresh eyes. To add another level of fun, pretend as if you are tourists and don't know your way around. You can ask for directions and maybe even get recommendations to places you'd never have visited unless you asked. 

If you are looking for a more romantic idea, try taking a boat tour of the city of Chicago. Granted, some cities not on bodies of water are conducive to this idea, but in those cases, a train or city bus tour can work just as well. In the case of Chicago, check out Shoreline Sightseeing Cruises. These affordable boat tours of the city allow you to see Chicago in all its beauty, but also because of their docking at Navy Pier, allow you to enjoy the sights of that facility as well, including the perfect first kiss spot, on the famed Ferris Wheel. Shoreline offers sunset cruises, that also serve as a nice first kiss spot as well. They are one of many companies that dock at different sites within the city, so rest assured that there is no monopoly of the waters of Chicago. Wendella offers wine tastings in addition to their tours, and Chicagoline works with the Chicago History Museum for their background information on the buildings of Chicago. Prices can vary and depend on your budget, what you are looking for, and length of time on the boat. 

If laughter is your thing, try going to a comedy show. Not the standard open mic night at the around the way comedy club, but a real comedy show. For under $15 per ticket, you can check out a show at the Improv Olympic Theater that will leave you in stitches. While it isn't an ideal first date activity, it is one that they probably won't forget. I've been to see Felt twice, and both times, I was very happy, and for $5, able to enjoy drinks at any of the local pubs after my show without feeling the burn in my pockets. It is a refreshing outing, something to create a good conversation after, and something to do any day of the week. For shows like Felt, try to buy your tickets in advance or arrive early, because they will sell out. This theater is one of many, but others are available. Don't be afraid to use google, citysearch or any other online resource to find a place you like if improv isn't your thing. 

These are just some ideas to get the brain working and the mojo flowing! I have not been solicited by any of these companies to feature them in my blog, just using them as examples. Do not expect the "Ashley Robin" discount, because hey, there's isn't one. I just want love and life to happen naturally. Speaking of which, next week, I will be hosting an internet radio show from 7pm to 9pm (Central Time). Visit the link for the station here, then click "Listen Live" and be connected. I will try to blog as soon as I end the show, and will post the topic of what I'm talking about, as well as how to call in once I make up my mind as to what that topic will be and if I'll be asking for guests. As soon as I do, I'll post all that info here. I'm so excited to be back in the booth again! 

*Ashley Robin*

PS- Big ups to one of my good friends since childhood, and fellow blogger, Zack, for featuring my blog as his "Spotlight Blog Roller". His blog can be found here, read it, it's refreshing, funny and honest. I read it all the time. 

vote in 2008!