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Bad Date Prevention


After a recent string of (bad) first dates, I’ve rethought how I’m approaching them. Is meeting in a potentially crowded bar the best strategy? Given the format of meeting for drinks, many of my dates turn into interviews or confessionals (fun story coming up!). The venue that you are in doesn’t give you or your date much inspiration. If you do not have natural chemistry, how do you deal with the potential awkwardness? You likely know some basic information about your date ahead of the meeting. Online dating profiles, Facebook, LinkedIn and Google Searches can answer many questions you may already have ahead of your date. Sometimes, I forget what information was disclosed on my date’s OKCupid profile or what I found through my own sleuthing. I’m working on curbing this habit. Due diligence appears to be a wise choice but it can backfire. An online footprint cannot defend itself and I do not want to be too judgmental (easier said that done). Sometimes, the less you know the better! On the other hand, not enough information can be terrible if not traumatizing…


Recently, I met someone from OKCupid for a drink at a neighborhood pub. When I first set my eyes on him, I realized that his online photos were deceptively flattering. I (barely) recognized him from his photos. As soon as he started talking, I knew why I typically prefer photos with a smile. I noticed he was missing a tooth in a fairly obvious spot. During our date, I don’t recall him making a comment that it had fallen out on his way over. I do remember, however, him sharing a story about a recent rosacea flair-up and his bulk toilet paper buying habits…really interesting shi…stuff! I’m not sure about you, but I’m not going to be swapping intimate and unflattering personal details 15 minutes into a first date. Don’t you hide all of those flaws until you’re in a relationship? No? Never mind.


Several weeks ago, I felt as if I was being interviewed for a position instead of chatting with a date. Instead of a natural “ping-pong conversation,” I was assaulted with rapid fire questions. I attempted to learn something about my date beyond short responses followed by another question. This was painful. What this date had in looks he lacked in communication skills. I didn’t realize I scheduled my date through Career Account. Eek!


These two dates highlighted two potential first date pitfalls: 1. The date will turn into an interview; 2. The date will turn into a confessional. The reason for the first scenario (interview) is likely an unwillingness to share personal information (because s/he is too guarded). The reason for the second scenario (confessional) is likely a lack of interesting things to talk about or nervousness (s/he becomes too open). This led me to think about changing what I typically do on first dates. Instead of meeting for drinks, why not do an activity? This strategy naturally gives you a shared experience to talk about. Even if the person you meet ends up not being your cup of tea (or is missing teeth), you will still have a fun evening! Planning can be overwhelming for many people. From my experience, it can be particularly overwhelming for men to plan dates. This is a leading reason for a bar to be a default date. Like choosing IBM, no one ever got fired for suggesting drinks as a first date. Why not make the experience more exciting? By changing the venue or format, the date may not default into a bad experience.


I started to get inspiration for this article after attending a House of Walker event. Johnnie Walker hosts high-end consumer-facing events that would be a perfect option for a date. In addition to having a great time at the event, I did not have to pay – it’s free! A couple of weeks ago, I visited the Chelsea Brewing Company (listed below) with my block. We went on a free tour and enjoyed a beer sample. It was a fun event in a format different than just meeting for drinks.

If you’re interested in reading more, check out my blog post for reviews on these two events:


I realize everyone reading this may not be in the same situation as me (single). With this in mind, I’ve listed date ideas by relationship stage. Due to length or expense, certain suggestions are best left for later stages in the relationship. The last thing you want to do is pick a long & expensive event to attend with a complete freak show. These ideas are also fun to attend with friends and family at any time! J

  • First Date: Keep the time commitment and cost low! If the date sucks, you want to be able to get out soon!

  • Second Date: Featured events are up to 2 hours and under $40 per person

  • Third Date: Longer events that are more expensive

  • Pre-“DTR”: You don’t need to define what relationship you’re in to enjoy this event, just make sure you can stand this person for 3 hours or more!

  • Established Couple: These events have a romantic tone and would be incredibly awkward for a first date…or maybe that is your style. No judgment.


Guarantee You Will Enjoy Your Experience (Even if it’s a First Date) with These Ideas!

First Date: Brewery or Distillery Tour ($)

Chelsea Brewing Company (

Pier 59, Chelsea Piers (btw 18th and 19th Street)

Free brewery tours are given on the hour every Saturday starting at 2:00PM (last tour starts at 6:00PM).

No reservations necessary.

  • Free sample of beer on the tour

  • $4 pint tickets to use afterwards (for purchase)

Kings County Distillery (

63 Flushing Ave, Brooklyn

Tours and tastings are from 2:30PM to 5:30PM every Saturday. The tour lasts about 45 minutes and run every 20-30 minutes. No reservations necessary.

  • The tour, which includes a tasting and admission to Boozeum, is $8

  • This is the oldest whiskey distillery in New York City!


Second Date: Attend Vino-Versity! ($$)

Vino-Versity: An Education Wine Store

1657 1st Avenue (btw 86th and 87th Street)

Social Tasting Events (every other week) from 6:30PM – 8:30PM; include 20-24 tastings and 10% off featured wine


Upcoming Events

Wine & Wines of the USA (Tuesday 11/19 @ 6:30PM, $36pp)

  • Featuring wines from CA, WA, OR, NY, NM, VA, RI, and many others! Cheese and small bites served.

Wine and Chocolate (Tuesday 12/10 @ 6:30PM, $36pp)

  • Featuring Champagnes, Sparkling Wine, Port, Dessert Wines and Spicy Red Wines from all over the world! Assorted chocolate bites and dessert treats served.


Third Date: Education by the Glassful ($$$)

Astor Center New York City

399 Lafayette St (at 4th Street)

Upcoming Classes

The Cocktail Lab – Hands on Workshop (Monday 12/2 @ 6:30PM – 8:30PM, $69pp)

Old Word vs. New World Wines (Monday 12/9 @ 6:30PM – 8:30PM, $69pp)

  • Tasting that features eight wines from the Old World (Europe) and New (N. America, Australia, New Zealand and South Africa)


Pre-“DTR”: Attend an Exclusive Tasting Event ($$$)

The Craft Experience (

548 West 22nd Street (btw 10th and 11th Avenue)

Wednesday 11/13 @ 7:00PM – 10:00PM ($89 General Admission)

The Event features over 125 Breweries, over 30 Distilleries and Local NYC Food. A ticket covers:

  • Unlimited samples of hundreds of the finest beers and spirits

  • Delicious samples from local food vendors

  • Souvenir tasting glass


Established Couple: Great Cocktails and Free Jacques Torres Chocolate Truffles! ($)

Ayza Wine & Chocolate Bar (

11 West 31st Street (btw 5th Avenue and Broadway)

On Sundays, this spot features cozy candlelit tables covered in rose petals. If you make a reservation on the website and indicate “Romantic Sunday Special” in the Special Request Box, the chocolate is yours!


I hope these ideas give you inspiration to get out of a dating rut, if you are in one, or prevent you from getting in one! As students, we are pressed for time, juggling classes, clubs and life outside of school. With these activities, you will have fun even if you do not want to see your date again! If you attend any of the suggested events, please let me know your thoughts. You can reach me on Twitter @personalitini.


Happy Dating!