Holly’s Dating Tips for Guys Part 8: The Do’s and Don’ts of a Planning a First Date

DON’T plan to break a sweat. You may think you’re doing her a favor by choosing something action-oriented on a first date—especially if you’ve gotten a vibe from her that she’s outdoorsy and/or athletic—but girls more often than not want to use the first date to evaluate you as a potential mate. Oh, sure, you could totally go ahead and think you can show off your manliness by climbing Mt. Doom as she admirably looks on, but imagine your humiliation when you find out she’s a frikkin’ mountain goat and has to wait for you to catch up every couple of minutes.
But even more of a concern is what to wear. A girl has so rarely an occasion in her life when she can dress up nice in anticipation of it being appreciated. Don’t rob her of the opportunity. Even if you’re planning to go to a hole-in-the-wall Chinese carry-out (don’t plan on this), she’s still going to try to look nice. If you tell her in advance, “Hey we’re going white-water rafting,” my guess is her first reaction will be to contact her friends and tally their opinions on the subject, and after being told by seven of them how stupid you are for suggesting this as a first date, she will sit in her room and stare blankly at her closet and ask herself, “What the hell does one wear white-water rafting but still says, ‘Hey, I’m adorable…adorably waterproof?’” Don’t put her in that position.

DO bank on the knowledge that you’re at your best side by side, not eye to eye. It’s actually a fact that a man is a better communicator when he’s sitting side by side with a partner both facing the same direction than he is looking his partner dead in the eyes. Anthropologist Helen Fisher, author of Anatomy of Love, thinks this is largely due to evolutionary differences—men, in hunting parties, used to sit starting at vast expanses for hours on end waiting for prey to hop out of the bushes while women used to sit and have inane, unending staring contests with their progeny (I guess?). From this division of labor developed two different communication styles.

Women, for their part, obsess over facial expressions and this is why they will incessantly ask you during periods of silences, “What are you thinking?” Especially when they are first getting to know you, they will do their best to analyze your facial vernacular as to best understand what you are feeling even when you aren’t actually saying anything. While some of us are experts at this, we are all pretty decent. And if you’re lucky enough to get into a relationship with one, she’ll probably learn to read your face better than you’d ever imagine. This is partly the reason why women prefer face-to-face communication, because its intimacy betrays a lot more than you’d think.

But men, who are not generally keen on sharing emotions, prefer side-by-side communication, which allows for greater exchange of thoughts rather than feelings. This is probably true for you and you’re not exactly sure why; you sit with your dad on a couch watching a game and during the commercials start opening up about shit for no reason or you’re driving in a car with your mom and you talk about stuff you’d feel horrified to discuss face-to-face. Though almost every dating guru in the world wants to tell you to make eye contact with your date (and you shouldn’t necessarily ignore that advice), there’s something to be said about the bonding intimacy of actually talking to one another. But then, I’m of the persuasion that a healthy conversation is worth substantially more than a night of staring across a table from one another with nothing to say (which always seems to beg for the rambling of utter crap by the party made most uncomfortable by the awkward silences).

For this reason, I suggest some dating strategies that incorporate this bit of knowledge. Technically, you sit side by side at a movie theatre, which is comfortable, but you can’t actually talk to one another. However, walking in a park is a side-by-side activity as is sitting side by side by a pond. Museums are always interesting and offer a constant stream of conversation fodder, which takes the focus off of staring at each other. Zoos and aquariums achieve this, much to the same effect. Though dorky in theory, pottery-painting in practice is one of those activities that is just mindless enough to talk through. And though

DO avoid competition. I’m not a big fan of advising couples to do competitive things which pit them against one another in any way. I guess because the couple-thing to me implies unity and competition implies the exact opposite of that. If your hope is to maybe kindle a relationship, then you need to be on the same team, or, well, at least not start off things by being on opposing teams. And, just so we’re on the same page here, you never know (as hinted at above) if you’ll be the weaker sex in any proposed activity (I mean, are you 100% sure you’re a better bowler than she is? Are you emotionally stable enough to power through facing that defeat?).

DON’T do a group date, unless… both of you are absolutely on the same page that the purpose of the evening, as far as you two are concerned, is to get better acquainted with one another. Oh boy. Ok, story time. Once upon a time, I had two guy friends who went on a group date with three girl friends. First, this was a stupid idea. Second, I was not one of these three girl friends. Instead, I was the one three out of these five friends decided to call to clear up confusion about who was with whom and who had legitimate “dibs” on whom. This was a mess. I don’t exactly remember how this happened, but both guys were convinced they were on a date with the same girl, leaving the other two girls feeling rejected and angry, never mind the awkward tension between the two guy friends. Needless to say, this was not a successful date and so I don’t recommend group dates as first dates in any shape or form. Too many things can go wrong. And, most importantly, it violates one of my most important rules…

DON’T lose control. This is important because it covers a lot of dating territory. As far as I’m concerned, and I’ve said this plenty of times in the past, men pursue, women choose. Both possess agency, just in very different ways. That being said, the first date should be seen as an opportunity for a man to demonstrate his efficacy and that means NOT asking her what she wants to do. “Hey, you wanna go out sometime?” “Sure.” “I dunno…What do you wanna do?” is seen as wimpy. Better would be: “Hey, do you wanna go play mini-golf on Saturday with me?” Seriously. One of these is a flaccid way to ask a girl out. The other is proactive and confident. Guess which one girls prefer.

But “don’t lose control” also means avoiding situations that would take you out of the driver’s seat, so to speak. You don’t want to give off the impression that you’re not a studly, desirable male by being seen as anything less than independent. It’s hard for me to think of all the tiny ways you can be seen as less than efficacious on a first date, but keep in mind that most women need to see you as at least self-sufficient to feel secure around you, if not powerful and mountain-moving (I exaggerate, but it’s mostly true). I don’t mean beat her over the head with oozing machismo (especially weird, artificial shows of chivalry, like saying “Milady” and bowing) because you’ll make her feel uncomfortable. But it’s nice to know the only thing she needs to worry about in the date is getting better acquainted with you, not where to eat, what movie to watch, etc. I think too many men are scared to plan a date because they’re afraid of offending someone. But seeing as we as a generation of twenty-somethings generally royally suck at dating anyway, I’ll tell you there’s no rulebook about how to do this. There are only things that will make you attractive to a female and things that will make you seem wimpy. Planning a date is probably one of the least offensive ways to prove you’re a take-charge kind of guy.