Tag Archives: gentleman

How to Plan a Nifty First Date

First date jitters, you know the feeling: that gnawing pit in your stomach eating away at your confidence, making you wish you had never planned a date in the first place. Well what if I told you that you could do away with the dread and actually look forward to your date?  The first step is preparing yourself for the date, but now you have to plan the date. If you plan well, those first date jitters will not be from anxiety but excitement! Here are a few tips for crafting the best first date from my own dating adventures.

Note: These lessons are from my experience and thus lean towards the heterosexual point of view, but I hope these tips can apply to all kinds of relationships!

1) Do something fun: Save the movies for the 3rd date

Going to the movies is a classic date option, but from experience, it makes for a horrible first date. If you are meeting for the very first time, are sitting in a dark room where you cannot talk for 2-3 hours, and feel pressured to hold hands before you even know his last name, you are not in the best context for getting to know each other. Save going to the movies for the third date, when you’re starting to feel more comfortable and you can snuggle—if you play your cards right—on the couch at the local theater pub, drinking a beer and holding hands. I can tell you from experience, this is a great choice for a third date and it is best followed up by a steamy make-out session in the alley next to the theater.

“Do something fun” may seem like an obvious suggestion, but my emphasis here is on doing something. Going to the movies is not really doing something, it’s watching something. Going to dinner does involve eating, but little else to do besides talk. From my experience, the best first dates are when you pick an activity that you can both do together. This allows you to take a moment from talking about yourself and talk about what you’re doing, which takes the pressure off the date and makes it way easier to have fun and connect!

One of my best dates was a night of contra dancing. Yes, instead of dancing with my date all night, I spent the night being spun around by 60-year-old men until I was dizzy, but I smiled the entire time. And when I got a drink with my date afterward, we had lots of hilarious stories from the night to tell. Other great options for doing something on the first date are bingo, trivia (if you aren’t too competitive), or an art walk. The last one is such a good option for a first date that it tricked me into thinking I liked a guy, when actually I only liked going on the date. I broke it off a couple dates later when I realized that I had just planned too good of a date. So good, in fact, that a month later I saw that guy at the same art walk with another girl and when he saw me, he grabbed the girl’s hand and walked away in a huff. And I just thought, “Good job, man. You figured out that this is the best date in town. Go have fun.” And I wish the same for you.

2) Have a time limit.

Part of picking a date where you have something to do is so you don’t spend the whole time talking each other’s ears off. If, however, you end up going to dinner or to coffee or any place where it’s easy to sit there talking non-stop, I suggest setting a time limit. I don’t mean telling your date that he only has two hours to get to know you and after that he must not say another word. I mean know your stopping point. If you’re going out to dinner, have a time you think you should head home. Or if you’re really unsure about the guy, book something after the date. I once went to coffee with a guy and we sat there for three or four hours talking about nonsense, both knowing that we’d rather be somewhere else but neither of us having an out. This isn’t to be cynical and say that you should set yourself up in case the date doesn’t go well, but that you should remember: it’s just a first date. It doesn’t have to go the whole day. If you like each other, you’ll have plenty more time.

3) Offer to pay: ladies & gentlemen!

To pay or not to pay, that is the question—a question that has haunted me at least. There is a scene from How I Met Your Mother where Ted is trying to choose between a girl who he connected with on a first date and a girl who offered to pay. And he really can’t decide. That scene has stuck with me. On one hand, I was raised on the idea that men pay for dates. That is a perk of being a girl, right? On the other, if I don’t offer to pay, will he think less of me? (Thanks, HIMYM.) Or even worse, if he doesn’t pay, is it still a date? I’ve realized over time that these questions are silly. If the date is good, it won’t matter who paid. This wisdom however was learned the hard way:

In my previous article, I mentioned going on a date with a guy who—it turns out—didn’t really think of me that way.  What I forgot to mention was that during the previous “date,” we paid separately. Rebounding from that experience, on another date, I practically forced this new guy to pay. We were again going to a movie and when I stepped up to order tickets, I freaked out. I worried that if I paid, I would be sending the signal that this is not a date. So, I stepped aside and looked at him in a “Now it’s your turn to pay” way. He looked shocked for a moment and then said “Oh, I’ll pay.” The awkwardness was palpable! Luckily, the rest of the date went fine because—get this—it had no correlation to who paid. Unless you are only in it for a free meal, then you don’t need to worry about money, because that’s not the point. The point is to see how well you get along, not who can bank-roll your next holiday.

This is why I’ve now adopted this policy: I always offer to pay. If he says no and then pays, great! (It’s always nice to be paid for.) If not, oh well. As long as you’ve prepared yourself properly and picked something exciting for you to do, you’ll be enjoying the night too much to worry about money. Remember: it’s just a first date. So have fun!

Photo by Sara Slattery

Photo by Sara Slattery

How to Get a Nifty First Date

Raise your hand if you’ve had a bad first date? I’m guessing that most of you have. Well, my friends, so have I—many, in fact. And it is through these trials and tribulations that I have come to realize a good date is all in the preparation. You don’t have leave the fate of your date up to, well, fate. There is a lot that you can do to ensure a more successful date before departing on your romantic rendezvous. Let me tell you how with a few of my misadventures in the dating world.

Note: These lessons are from my experience and thus lean towards the heterosexual point of view, but I hope these tips can apply to all kinds of relationships!

1) Be clear that it’s a date.

You know how, in movies or TV, someone seems to always have the tenacity to ask “Wait, are you asking me out on a date?” with a sly smile and a knowing look? Well, I’d never have the guts to ask that and, if I did, it would probably be a shy awkwardly stuttered sentence like: “Date. ME?” If you’re like me, then it can be hard to be sure you’re either going on a date or (often in my case) clarifying that you are in fact asking someone on a date. For the latter, I find asking someone to an obvious date-like activity, say dinner and movie for two, is helpful. However, that doesn’t always work. I bring you exhibit A:

I had a crush on a guy who was kind of a friend, or at least had dated one of my friends (always a good place to start). We had started hanging out and I wanted to progress things to the next level, so I thought, Hey, you know what’s a great idea? Asking him to a movie via text, that’s what. This was my first mistake. A text is never a good way to transition a friendship to romance, let alone obviously ask someone out without the gratuitous use of winky faces. So, when I showed up for this so-called “date,” guess who was surprised to see only me standing at the door and tried to invite his roommate along? I’ll give you a hint: it wasn’t me. If you would like to avoid this fate, I suggest you make your intentions as clear as you can.

2) You don’t have to lay it all out there, but don’t be completely opaque.

As you prepare for your date, you might find yourself worrying over what you’ll talk about. What if you say something awkward? Or you don’t have anything to say? Or, in your fear of silence, you talk too much? This last one is my biggest downfall and why I advocate keeping the first date light and fun: no midnight confessions or blood oaths. Now, I am not saying for you to hide your true self away until you’re sure he/she likes you and then reveal your deep-seated love of unicorns. All I mean is you don’t have to tell all on the first date. Take it from someone who invited a guy on a first date to a poetry slam and thought it would be a good idea to sign up. I had just met this guy, and here I was standing in front of an audience performing a poem about my parent’s relationship while he squirmed in his seat. Talk about vulnerability. You do not need to do this. In fact, just don’t.

Though, you do need to be somewhat vulnerable. You have to share something about yourself, but more importantly you have to reveal your emotions. The only way the person is going to know that you like him/her is by showing it. Now, I am horrible at flirting, so I usually go with the more direct “I had a good time. Let’s do this again” approach. But even that can be confusing if interpreted as a line. So make sure to send a flirty text later or, better yet, set up the next date. Nothing says “I like you” like I want to see you again and maybe this time I’ll tell you about my unicorn obsession.

3) It doesn’t have to be romantic.

The first date is exactly what it is: a first date. Whether you’re looking for your soul mate or just someone to date for a while, the first date is like a test drive. And since it’s just a test drive, you don’t need to go full throttle (unless you really want to: #punalwaysintended). What I mean is it’s perfectly fine if you do not touch on the first date (I would consider that normal for meeting a stranger).

In the past, I had this ideal that the best dates were the sweep-you-off-your-feet romantic ones and every time I went on a date that didn’t reach those standards, it felt like a failure. And yet many of my most romantic dates ended up being assholes later or just looking for sex. One guy invited me to the top of his roof and as we were sitting there overlooking the sunset, he swept my hair out of my face and asked me what I wanted most in the world right now. I kissed him because that seemed like the most romantic gesture. Guess who never heard back from him? It was a great moment, but it taught me to re-evaluate my standards. These days, I don’t go into the first date expecting to find sexual tension right away; I save that for later. Right now, I just want to know if we can hold a conversation without it being painful.

4) Check your expectations

And this brings me to my final pre-date prep tip: remind yourself that you don’t have to decide right away. As I said, this is a first date, not a life-time commitment, so don’t treat it as such. If you are unsure about how you feel at the end of the date, that’s fine. You can go on another date and continue to test the waters. On the other side, if you find yourself falling for someone on the first date, you should also check yourself.

I have been on both sides of this spectrum. On one hand, I stopped seeing a guy because I thought I didn’t have time to date anyone I wasn’t sure about and in retrospect realized he could have been a great match for me. And then I have gotten my heart broken over a single date. It didn’t help that I was already obsessed with him before I even went on the date, but I could have saved myself some pain if I had followed my own advice.

This is why I say I don’t believe in love at first sight, but I do believe in heartbreak at first kiss. Be careful with your hearts, my friends. And try to remember: it’s just a first date. So have fun!

Photo by Sara Slattery

Photo by Sara Slattery