Step 7: Go On Some Dates (Dates 1-4)

Dating is a numbers game. You know that. So, why spend two weeks chatting with someone that takes three days to respond, or spend time sending emojis in text messages to someone with excuses every time you get together. If someone actually wants to date you, they’ll find a way. Don’t waste your time.

  • First Date – See things
  • Second Date – Watch things
  • Third Date – Do things

First Date

The debate is out on how long a first date should be. Some people opt for a half hour doing coffee or a drink. Others opt for something more substantial, or more creative. So, you pick what your threshold is. Usually when I’m burnt out of dating, I do quick half hour dates.

First Date Ideas:

Regardless of the length of time, as a rule of thumb, first dates should:

  • Give you an opportunity to get to know the person
  • Not involve something so distracting don’t communicate
  • Not cost too much
  • Not be be disruptive to your normal routine
  • Have an opportunity to go to a second location if things go well
  • (If you’re planning) Be somewhere you’ve been beforeOh and don’t forget to bring cash! Even if they pay, offer to pay the tip.

I know this all seems obvious, yet people opt for dinner and a movie far too often. Instead of dinner & a movie, try these:

  • Walk in the Park – Great for busy, athletic, extroverts
    Favorites for First Dates: Patterson Park, Wyman Park, Fort McHenry
    Pro-Tip: These are my favorites because they’re well maintained, well-lit, semi-busy, and within walking distance of food/drink options.
  • Art Gallery – Great for rainy days with psuedo-intellectuals
    Favorites for First Dates: Walters Art Museum, Baltimore Museum of the Arts, American Visionary Arts Museum, Reginald F. Lewis Museum, Museum of Industry
    Pro-Tip: Most are free, others tend to have Groupons & Living Social deals, so look out for those.
  • Thrifting/Book Stores/Record Shops – Great for Hipsters
    Favorites for First Dates: The Book Thing, DeBois Textiles, True Vine, Atomic Books/Celebrated Summer, Bmore Flea
    Pro-Tip: Head to Hampden or Fell’s Point for a concentration of books, used clothing and vinyl.
  • Indoor & Outdoor Markets – Great for cheap brunch dates
    Favorites for First Dates: Farmer’s Market Under 83, Lexington Market
    Pro-Tip: Pick one that is large enough to take some time to get through in case it’s going well.

Second Date

If you’ve decided you wanna see this person again, now’s the time to have fun! On the second date, you can be a bit more distracted. You should try to do something that is the antithesis of what you did previously also, just so you can get a feel for the person in different settings.

Second Date Ideas:

  • Comedy/Improv Show – Great to test your date’s sense of humor
    Favorites for Second Dates: Second Saturday Shit Show at Ottobar, B.I.G. LAUGHS Comedy Night at Midtown BBQ, Chucklestorm
    Pro-Tip: Sit in the front row if you want to make things interesting. Do some stand up at an open mic, if you really want to stand out.
  • Science Center/Aquarium – For the kid in you!
    Pro-Tip: Friday nights at both normally have great deals, they close late and there are way less children.
  • Outdoor/Drive-In Movie – Great for people that talk through movies
    Favorites for Second Dates: Bengie’s Drive-In, Outdoor Films: Wyman Park, Little Italy, Federal Hill
    Pro-Tip: If you can bring your own food, go the extra mile and get a little fancy so it’s a spin on the average dinner and movie date. If you opt for outdoors don’t forget blankets/chairs and bug spray.
  • Watch “Sports” – For the sports fan on a budget
    Favorites for Second Dates: Charm City Roller Girls
    Pro-Tip: I don’t generally recommend any event you have to pre-pay for this early on but if you already have a season pass or free tickets, might as well! If you’re a fan of pro sports, without the pro sports money, hit up a college or high school game instead.
  • Burlesque/Drag Shows – To get things a little spicy!
    Favorites for Second Dates: Gallery 788, Ottobar, Metro Gallery, The Hippo
    Pro-Tip: Make sure your date is up for seeing boobies before you plan this one.
  • “Progressive” Meal – For those who just want to eat.
    What Is It?: When you go to a different restaurant for each part of the meal: appetizer, entree, dessert, drinks/coffee
    Pro-Tip: This can take a long time which is why it’s better for a second date. It also takes a bit of planning if you intend to walk everywhere (which you should), don’t pick a place for dessert that doesn’t serve it.

Third Date

This is usually a make it or break it date so make it count. The best part of the third date is that you can go on adventures, see someone in a lot of different settings, and you can spend some time not just focused on each other. Third dates are perfect for, my favorite, the all day date!

How to Plan a Third Date

  • Plan Ahead
  • Be Cohesive
  • Start Early
  • Include a Meal
  • Have an Activity
  • Have Adequate Transportation/Parking
  • Take Into Account the Weather
  • Have Alternatives
  • Be Open to Suggestions

Third Date Activity Ideas:

  • Bowling/Mini-Golf, Skeeball
  • Classes
  • Bike Party/Bike Routes
  • Geocaching
  • Volunteer
  • Farms
  • Arcade/Casino
  • Dancing
  • Brewery Tour
  • Plays/Concerts
  • Amusement Parks
  • Street Fairs
  • Music Festivals
  • Drinking Events

Check out the neighborhood tours section for full all day date plans.

Fourth Date/Getting Comfortable Date

This is when you’re used to each other and can call/text them on the same day asking to hang out during the week. This date is normally a few hours after work and involves dinner and possibly meeting up with friends.

Fourth Date Ideas:

    • Karaoke/Trivia – Great for showing off or embarassing yourself.
      Favorites: Karaoke: Lithuanian Hall, Trivia & Karaoke: Ottobar, Midtown BBQ, Sticky Rice
    • Game Night/Bingo – Great for introverts
      Favorites: Brews & Boardgames, The Bun Shop, Golden West
      Some places have organized game nights while others just have board games available. Alternatively, pop by Canton Games and pick something up for the two of you to play or invite over some friends.
    • Watch TV/Movies in a Bar – Great for those without cable
      Tip: Some bars will have weekly movie nights or will show popular TV shows (i.e. Walking Dead, Breaking Bad, Doctor Who). The problem with this is, it’s rarely published so you just have to “know” or hop they mention it on social media. That being said, it’s a good way get dinner/drinks, keep up with your favorite show, and put in some face time with someone you’re into.
    • Movies – For those who like the classics (or lack originality)
      Tip: Unless you’re dying to see Tranformers 8 or whatever, keep things a bit more interesting by experiencing classic and independent films at Baltimore owned establishments.

      • The Charles Theatre: Cinema Sundays, Revival Series
      • The Senator: Special Showings, The Met Opera, Family Saturdays (only $5!)
      • The Maryland Film Festival
      • Enoch Pratt Libraries
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