Navigating dating apps: How to maximize your options

Editor’s Note: This is the first article in a three-part series that explores modern dating in the District from WTOP’s Rob Woodfork. Stay tuned for tips on affordable dating spots and even relationship advice from the experts. 


In sports, we call this time of year “the dog days of summer.” It’s the period when the NHL and NBA postseasons have come to a close, and it’s so early in MLB that it has yet to really matter.

In a way, this label also applies to dating in the District. The summer weather may be conducive to going out more often, but it certainly doesn’t ensure the quality of these outings will keep up with the quantity.

That’s where I come in. To help you combat this summer slog, I’ve talked to experts and mined for some of the best spots in D.C. I’ve even broken the “Dog Days of Dating” down to three parts: how to get ’em, how to wine ’em and dine ’em, and how to keep ’em.

We’ll roll out one part per week, so I promise it’ll be easier to read than your prospective date’s LinkedIn profile (because admit it … you do some cyber sleuthing before the first date). 

Here we go: 

Online dating can be daunting, annoying, time-consuming and frustrating.

Incidentally, it’s the preferred method of meeting potential partners in 2017.

For better or worse, there’s less stigma attached to online dating and more and more people view it as a legitimate way to meet people, Pew Research reports. In fact, more than 91 percent of single people in the United States have at least tried online dating.

This, however, is no guarantee we’ll fare any better than we would offline, exchanging numbers with some attractive stranger at a bar or in the produce section of the grocery store.

Admittedly, I’ve tried multiple online dating apps in recent years with varying success. I’ve met some really great women and also went on some dates that were best suited for a Netflix original comedy.

The sites you choose matter a lot: Tinder’s evolution from hookup app to dating site has rendered it a jumbled mess, while OKCupid profiles (assuming they’re filled out properly) are detailed enough to allow users to weed out what I jokingly refer to as “hotties with deal-breaker qualities” even before an initial introduction.

I learned a lot through this process, so it’s only right that I share this knowledge. Think of me as your own personal Hitch (without the wicked seafood allergy). Though I can’t walk you through the entire process, I can offer you five ways to make your profile stand out.

1. Pics matter

Let’s be honest here: No matter what you say in your profile, your picture is the first thing people are going to look at. So if you only bother to post one or two selfies, you’ve inadvertently announced you’re alone and nobody’s interested in taking your picture.

Any online profile should include a minimum of five photos, featuring at least one of the following: a clear look at your face, your smile, a full body shot, an action shot (i.e. you engaging in an activity such as softball or running), and a formal shot (doesn’t have to be black tie, but have on a suit or a dress). This way, there are no surprises on the first date (at least not because of appearance).

Furthermore, I’d rather someone decide they’re not that attracted to me before I’ve invested any time and money into a meeting.

You’re best served by cropping other people out of your pictures, especially if you’re a straight person in a photo with someone of the opposite sex. You may know that’s your sibling/cousin/best friend, but it’s a visual potential dates don’t need to see, especially without context. Plus, nobody likes having to play an impromptu game of “Where’s Waldo” featuring some guy/girl they don’t even know.

2. Answer as many questions as you’re comfortable with

Here, I’ll use myself as an example. While on OKCupid — which has a battery of questions, ranging from the innocuous “are you a pet person?” to some pretty graphic and deeply personal stuff about sex — I answered as many as I was comfortable with so women could get an idea of what I like and what’s important to me before we even meet.

I wouldn’t even message someone who doesn’t answer at least a fair amount of questions. Personally, I would immediately hone in on two in particular: I need to know a woman’s religious preference and if she has a problem dating a man with a child from a previous relationship. If we’re not on the same page on those two topics, it’s best we don’t even get started.

If you’re on a site that allows you to reveal more than just superficial information, you absolutely should. Again, it’s best for everyone involved if you’re able to weed out potential deal-breakers in the discovery process rather than getting two dates in and finding out he/she has no interest in being a stepparent, attending church, or sharing a bed with you and your spoiled German shepherd.

3. Don’t complain

I know every horrible thing straight women encounter on dating sites. You know how? Too many women complain about it in their profiles.

This may be cathartic for you, but it’s a red flag for the prospective date. I would automatically swipe left/hide from view anyone engaging in this because if they’re complaining to strangers in print, they’ll almost certainly complain to you in person. I don’t feel that’s insensitive; I’m fully aware there are some nasty dudes out there with no idea how to carry themselves appropriately and I genuinely empathize with the women that have to cope with that. But the good guys are going to be turned off if they get the sense you’re negative and/or dramatic. So why not take the high road and keep your profile positive?

This goes for you too, fellas. The last girl ghosted you and the one before that wanted someone in a higher tax bracket. That’s life, bro. Complaining about it in print will make you look bitter and will likely scare off the next one. Shake it off and stay positive. Neither gender is all bad.

4. Have a good icebreaker

As gender roles continue to evolve, this is actually good advice for everyone bold enough to make the first move, not just straight men. Opening with a simple “hi” doesn’t do anything but increase the likelihood you won’t get a response. If you tie an icebreaker into a nugget you actually read in their profile, it demonstrates a genuine interest (or at least basic reading comprehension) and gives them an opportunity to expound on something of interest to them.

For example, I saw someone I liked and, in her profile, she mentioned she’s really into Marvel comic books. So I sent her a message saying, “Hi (name)! It just so happens I’m a huge comic book geek myself. What did you think of (the recently released Marvel movie)?”

Thus, writing an icebreaker into your profile is a helpful way of offering potential dates an opening. All of my profiles had a line from the movie “Anchorman” in the first paragraph and ended with, “Ask me about my Biz Markie story.” Though on average, I probably initiated three out of four online conversations, my setup allowed a woman to open with something like “I see what you did with the Anchorman reference … I love Will Ferrell movies!” or “Tell me your Biz Markie story!”

5. Close the deal

Nobody’s on these sites to meet new pen pals. Some people like to talk on the phone before meeting and others prefer not to give their number out until meeting someone to make sure they’re not a weirdo. Regardless, if the conversation is going well and it seems like there could be some chemistry, ask to meet up.

Dating has evolved, so committing to dinner and even a drink or two is presumptuous (and expensive). Why not be creative and go for ice cream instead? Walking and talking with gelato in hand and monuments in the background is a great way to get to know someone with no pressure.

Take the week to ponder these things. Next week, we’ll tell you where to take the person lucky enough to pass “round one” of your dating bracket.


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