Tips For Men: Better Dating Conversations

I reached out to my good friend Will to do a blog post for me since he’s someone who is super-confident in the dating world, and though his advice always has a little dose of silliness, it’s usually spot-on.

Without further ado, here are his tips on how to carry a great conversation on a date:

  • Wing It: Some guys like to meticulously plan out every question and topic they want to bring up. Please learn how to have a fluid conversation without doing this. Women do not want a robot, they want a human being. Plus, it will save some awkwardness from pulling out the list of topics you have in your back pocket when you get stuck.
  • Be Nice, But Not “Fake Nice”: Being respectful is always important, but do not be so nice to the point that it doesn’t seem genuine. When someone tries too hard, it’s obvious they only have one goal in mind, and women aren’t stupid… Krista’s readers are intelligent, so you fellas are looking for someone with brains too (Not in a zombie sort of way, even with Halloween coming up and all).
  • Utilize Your Intelligence: This article is discussing what to do when dating quality women, so onward to the next tip — intelligent conversation. Women love to talk, so when they’re talking about themselves ask questions that you’re naturally curious about. For example, if she’s not from around here, ask her about her hometown and how different the culture is there.
  • Bond Over Hobbies: The best way to keep a conversation going is to talk about hobbies. On the first date, ask her what she likes to do and if you have some things in common, talk about that. Easy money! A good partner is someone you can do fun things with, so finding her interests early is awesome. For example, I’m a huge fan of basketball, so it would be advantageous to me to meet a lady who also knows that ball is life, since women that don’t know will never completely understand.

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  • Have A Sense of Humor: This is my bread and butter, my meal ticket. Women love a guy who has humor and wit. As a matter of fact, if you make a girl laugh frequently and you do not screw up too bad, you’ll most likely have a second date. I’ll bet $100 on it. Just don’t be too crude (my Achilles heel sometimes). If you want more detail on how I include humor on a date, pick up my new book Making Her Fall Head Over Heels… With Laughter. The book signing is actually next Thursday.
  • Be Confident, Not Cocky: Confidence is knowing you have the ability to do something without having to brag about it. Whenever someone says they are really good at something, I automatically question their claim. For example, if I titled this article “Reasons Will is the Most Charming Person on the Planet,” you, as the reader, will nitpick anything that can be interpreted otherwise just to disprove my point. Your date will do the same thing. I better take my own advice; my dates won’t know about my book.

Today’s lesson (Courtesy of Will): To sum it all up, just be authentic and have fun. Keep trying; a failed date is never a bad thing and honestly will likely happen more often than a successful one. Just learn from your mistakes (and victories!) and you will be a force to be reckoned with. Relax, bro!

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Fast Five: Pre-Date Jitters

I have been on my fair share of first dates now, and I’ve figured out some pretty good standard practices to make first dates go a lot smoother. Here are a few quick tips to take some of the jitters out of a first date:

  1. Have a few different “date” outfits picked out. For example, when I first started dating in the winter I had two first date outfits I would wear depending on my mood. The first was a gray V-neck sweater with leggings and black heeled ankle boots (Right, Robert?). The second was jeans, brown leather boots, and a ballet pink lacy t-shirt. By having specific clothing as my “go-to” date outfits I never had to worry at the last minute that I didn’t feel good in my clothes. If I feel edgy I’ll switch things around a bit, but it’s nice knowing that I have two killer go-to outfits.

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    Aaand summer calls for swapping out the sweater for a lacy tank! I also always paint my nails different colors — that’s my one beauty must-have.*
  2. Create a “dating playlist” to jam to on your way to the date. Even after dozens of first dates, you still sometimes get a little case of the butterflies before going out. By listening to feel-good songs you can dance around in your car and forget about any of the anticipated awkwardness.
  3. If you’re talking to a couple of people at once, go back and do a quick overview of the conversation you’ve had with your date. It’s obvious people usually have a few options, but is still kind of embarrassing when you mix someone up with another prospect. Something about meeting someone in person for the first time helps you remember details about them, but before that it can be easy to confuse one online date with another.
  4. I like looking over a menu before going to a restaurant if I am concerned about working around my food allergies (I have acquired many the last 2 years — what kind of 25-year-old doesn’t know they’re allergic to tomatoes and potatoes?!). That way I can relax and enjoy the date instead of take twenty minutes to customize an order.
  5. Remember to relax and have fun! The person you are out with agreed to go on a date with you, so there is something there. Even if you just have another notch in your dating belt after, you’ve also gained a new experience and collected another story to tell.

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Do you have any other ideas to make dating a little bit easier? I’d love to hear about it in the comments. 🙂


*Photo taken by my beautiful friend Audrey! Check her out if you are in the DMV and need a photographer for anything.

#TBT To Being An Olympian For The Day

Today I’m going to share a story I like to tell on a first date if a guy asks about my love of pranks (Which I have listed on my dating profile as a favorite activity).

My best friend and former roommate Audrey and I studied abroad in London during the 2012 summer Olympics.

We make a really great pair because she is more “type A” and makes sure any necessary plans we need are all taken care of, but I am more “type B” and ensure enough spontaneity (read: disorganization) to have a fun time. Playing pranks together in college was always a blast because of the ideas and action on my end, and planning ahead to make sure we wouldn’t get ourselves into a bind on her end.

Anyway, I got a tip that they were selling a few official Olympic jackets at the USA House. As I said before, I love pranks and have a mischievous mind, so immediately realized this was a great opportunity. I found Audrey after our classes were over and told her we needed to get on the Tube and head towards South Kensington. I explained my idea on the way, and Audrey was completely up for the prank.

Basically we plotted to purchase these jackets and wear them, along with other Nike gear, to the Olympic Village –a giant outdoor mall where all of the athletes hung out– and see if we could fool people into thinking we were real Olympians. We were lucky enough to snag two jackets in our size, and giggled as we hurried to The Village. 

Our excitement grew as we pulled up to The Village, but was quickly stifled when we walked around for ten minutes and nothing happened. After we made a few more laps we concluded that this was not going to work.

Until all of a sudden two little American girls ran up to us with paper and pens asking if they could get our autographs.

We kept our cool, smiled at them, and said, “of course.”

I don’t know if you’ve noticed this or not, but people really are like sheep. When they see any sort of crowd gathering, they will follow, whether or not they know what’s going on.

This fully worked to our advantage. As soon as the girls came up to us, others took notice. A line quickly formed to get photos with us, and just kept growing. We ended up having dozens of people waiting in line just to take a picture with us within a matter of minutes. It was crazy!

We got asked questions about our events and sloppily signed our real names when people asked for our autograph. Before we got to The Village Audrey and I had decided that our story was that we were on the USA swim team — she was a diver and I was a swimmer. This was perfect, as I swam through high school and could answer basic questions, and because Audrey is significantly shorter than I am, so there isn’t really any other sport that we both could have played.

The funniest thing to me was that many of these people were going to upload these photos with us to Facebook when they got home. They would come up with captions like, “We met Olympic swimmers today!” and proudly display these photos as a new profile picture — photos of two completely random American girls.

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We even ended up meeting a real former gold medalist for the USA basketball team, who was super excited to meet a few of the female swimmers because “swimming is his favorite sport to watch.”

For the most part my dates seem to think this story is pretty entertaining, and I have heard some pretty awesome prank stories from the gentlemen I’ve gone out with as well. I have also realized that I talk about Audrey almost as much as I talk about myself, which is fitting because everyone knows girls come as a package deal with their best friend.

Today’s lesson: You don’t have to work hard to get credit for being an Olympic athlete — you just have to be a convincing enough actress to make people believe you are one.