Dating 101: Online Dating


by Randall S. Frederick (@randall_scott)

Four years ago, I moved to California to restart my life and, at the suggestion of a friend, signed up with a few online dating sites to meet new people and force myself to socialize outside of my immediate circle. I did and it was fun – meeting people turned into dating a few times, all very low-key, “fun” more than anything serious. About two years later, my friend Dani was pouring out her recent dating woes to me – how men sucked, how she just wanted to have fun and not feel too much pressure – so I did what my friend had done for me years before. I told her to sign up for online dating.

If you knew Dani, you would have known this was going to be a long, arduous journey. Dani is a great girl – smart, funny, beautiful, “a catch” as the matchmakers would say. But she has an aversion to the idea of “dating.” Raised in a conservative environment, “dating” seemed confusing and a bit weird to her. Over time, the idea of relationships and kissing and the whole dance of blending together seemed more and more strange to her. When we met, Dani was thinking about becoming a nun. No joke. And, having known a few nuns (I even dated one – but that’s another story!), it never felt like the right fit for her. She wanted to share her life with someone, and seemed so… un-nunish (not a word, I know that, let’s get past it) underneath all of the bluster. So one day, I ambushed her. A mutual friend and I literally sat Dani down and signed her up for an online dating site. As we filled out the forms and questionnaires, Dani alternatingly giggled and whined – it was fun and scary for her. A week later, Dani went out on her first online date and when I saw her a few days later, she told me she had fun! “So much fun!” The guy took her rock-climbing and then to a trampoline center, so she had a great time. It wasn’t long before she had her second date, then her third, and two years later she’s still going at it, meeting people after she recently moved to Milwaukee, she’s still going out, having fun, sometimes not having fun, and making memories in the process.

I asked Dani this week if she would help me talk about online dating. She’s the perfect person for this. She’s been doing it long enough to know the ropes, but not so long that she’s become unenthused and disappointed with her prospects. So here goes!

Dani B., 28yo, Community Development Coordinator in Milwaukee

1) Don’t use pet names. I don’t know you, you don’t know me. That’s why we’re chatting online and (maybe!) going on a date. Calling me “baby” or “sweetheart” is way too intimate. In fact, it’s a false intimacy – like Randall says, “Don’t ‘Bro’ me if you don’t know me!” Besides, using a person’s name when you address them has psychological benefits. You’ve got a better shot just calling me by my name.

Randall – Yeah, what’s up with that? I’ve been told I can “sweet talk” and “turn the charm on” when I want to, but even as I’m doing that, I’m being very, very careful with it. It’s not just guys, though. I’m flattered but still a little cautious when women start talking that way to me. I met a woman for drinks last week and was keenly aware that she kept calling me “boo.” I found it funny, but not in the good way.

2) Ask me silly or weird questions – nothing too deep because depth takes time and trust. Don’t just ask me how I am when you want to talk to me. Ask me something I can put thought into. For example, “Would You Rather…” is a good question to ask because it can tell you a lot about who I am but also allows me to be lighthearted too.

Randall – Absolutely. Great suggestion. The art of conversation is not data collection, it’s about getting the person in front of you to comfortably open up and for both of you to have fun sharing your time together.

3) Show interest. Maintain that level of interest. Ask me questions. People want to be wanted. They want their opinions and thoughts to be heard and welcomed. They want their hearts to be pursued. They want to share who they are and be seen, heard, known. Ask me leading questions about things from my profile, things I talk about when we meet, things I’m interested in, and I will absolutely reciprocate.

Randall – I told Dani, in response to this, that I went out on a first date with a scientist from Jet Propulsion Laboratories who showed zero interest in what I had to say when she was sober and even less when she had downed half a glass of wine. Mid-beer, I put my bottle down and said, “I’ve had enough” and walked out.

4) Do not ask any questions that would lead to bedroom talk or thoughts of sex if we have never met in person. Flirting is okay, but be charming. Be confident. Don’t be sleazy or weird. A guy recently asked me how good I was at pillow fights and if I could defend myself. First off, I am not a child. Second, that was a creepy question and it assumes we would ever be alone together. After that, we never will.

Randall – Abraham Lincoln once said, “The people who talk about sex the most are usually the worst at it.” Okay, maybe he didn’t say that. But rushed intimacy is awkward for everyone (and WTF was up with that pillow fight question?!). I’d just as soon invite a woman over to my apartment and see what happens before passively making insinuating comments all night. It’s all about confidence. Dirty talk? That’s not confidence. That’s cheap thrills. You want to have sex with this woman? Say so. Just don’t be a perv about it or make her feel unsafe.

5) Make plans for the evening clear unless we’ve been dating a while or you are planning a surprise adventure. That way, I can be prepared for what we are going to do. I recently went on a date where the guy clearly just wanted drinks. I had just gotten off work, so I was hungry and even the waiter could tell. Ridiculous! If we’re just meeting for drinks? Say that. I’ll know how to dress, what to expect, and be able to schedule the rest of my night.

Randall – Preach, girl! I can think of no greater aspiration than a man who “handles his business” and lets his date know relevant details so she can handle hers.

6) Don’t get too serious too fast. A guy told me on a date the other night that I was “the kind of woman he would want to marry someday.” Okay, first off what does ‘some day’ mean? Am I not good enough right now? *haha* Second, as cute as he was, that was a really big jump from getting-to-know-you questions to telling me you want to marry me.

Randall – When a man says something like this, he is trying to share his confidence. He’s saying, “I’m enjoying myself. I’m having fun. I want to keep this moment for as long as possible.” Still, it’s rushing things and comes off as desperate more than anything else.

7) Don’t idealize me. I am a person. I have faults and weaknesses; when you tell me I am your “ideal woman” or that I am the kind of person you want to marry, it puts a ton of pressure on me too soon. Let things be easy and naturally move into something more, that’s how you show me you’re serious.

Randall – Yes, yes, yes! This is one of the biggest mistakes a person can make – not just guys, but women too. When you idealize your partner, you make them an Idea. They cease being a real person. Any “mistake” they make, any way that they deviate from the Perfect Person you’ve made them out to be is trouble for everyone involved. They will never live up to that inflated Idea you’ve created.

Speaking of ideas, here are a few more from me.

  • If even one of your online photos involves you in panties, then you are inviting sexual comments. Don’t be surprised when that happens. Listen, I’m as Feminist as they come, but think of it this way. If my profile photo was a dick pic, you would probably never notice that I have two Masters degrees and own my own business. Your first impression of me is that I showed a dick pic. Stop pretending to be insulted when a guy makes sexual comments. Or – in my case – when he ignores you.
  • If you are boring, don’t blame your date for not making conversation and being unimpressed with you. I’m a great conversationalist. When people first meet me, I come preloaded with easily 100 questions to get us talking. So if we start messaging or texting and I’m not responding? It’s because you are boring the shit out of me. That said, it’s also important to give people a chance. If you finally go out and meet this person and their personality isn’t as catchy as it was online? That’s okay. It happens. Some people are better at communicating in writing. Learn to love their awkwardness, allow them to talk and open up at their own speed, and hope things will get better as the night goes on.
  • OMG, the obligatory wine photo. Snooze. No matter how amazing a woman’s online profile is, if she has a photo of herself holding a wine glass, she becomes Basic in my mind. The same is true of a “Bro” holding his bottle of beer. There’s nothing like the cliché of a late-twenties/early-thirtysomething smiling with alcohol. Want to do something different? My friend Audrey Bellis visits her family almost every Friday and smokes cigars with her dad, then posts the photos on Instagram. That’s some fuckin’ A-Game right there.

Okay, so all of that said, meeting and dating online are perfectly great ways to meet people. In a 2013 Pew Research study, they found that 29% of American couples who got married that year had met online. Whaaat?! That’s almost one-third of every couple! And while 54% of those polled (both married and unmarried) said that they felt their date had misrepresented themselves online (don’t lie!), 59% still said it was “a good way to meet people.”

For me, using online dating sites was a great way to meet people. I didn’t go into it looking for a spouse, I went into it with lowered expectations. I was perfectly happy just meeting new people, hearing their stories, making connections, and making friendships. Some of those friendships became “something more” and, like traditional dating, sometimes you meet a few unpleasant people but it all shakes out to make for a few laughs and sweet stories with friends.

Moral of the story – Try it out. Online dating is a good thing.

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