Listen Up Boys: A Bit Of Online Dating Advice

My parents met in a bowling alley. My grandparents met in a grocery store. Today, stories like this are scarce as people are taking less relational risks. Instead, people are more likely to engage in dating behavior that minimizes the likelihood of rejection. For example, it’s more common to date a close friend than to risk striking up a conversation with a cute stranger in a coffee shop. This is also evident in the rise of online dating. Some statistics suggest that, today, over a third of relationships start online.

As we transition into this new way of forming relationships, it’s important to be mindful of our blind-spots. For ages before us, people learned relationship skills through observation and a sort of relational-osmosis. Parents and grandparents made a habit of sharing the stories of the initial stages of their love. Through these stories, younger generations learned how to ask someone out, how to handle rejection, and how to act (or not to act) on a date.

However, when it comes to online dating, we are creating the rules. As the first generation to fully embrace this new technology, we’re lacking a cultural framing of how to utilize it to its fullest potential.

Personally, my online dating experience started out as a joke. A sort of social experiment, so to speak. As I started to write about my crazy online dating experiences, however, people opened up to me. Women who hadn’t told even their closest friends that they were on online dating sites started to confide in me. People who have been looking for love online for years wrote me stories about their biggest frustrations with this new form of dating. As I’ve listened to their stories, several common themes started to emerge. Themes that I think could be really helpful for guys to understand as you seek to build a meaningful relationship.

Which is why I, as a women, am offering a few tips to help men understand the female psyche when it comes to navigating the mysterious world of online dating.

1. Quality over Quantity

The number one complaint I hear from women is, “I feel like his first message is either a) disingenuous and too general—as if he sent an identical message to multiple women or, b) is trying too hard to get my attention by being completely outlandish.”

The number one complaint I hear from men is, “It’s too hard to get a response from women.”

I would agree that men try to build connections with too many women at once, in an attempt to have greater odds at a response. Not only does this come off as insincere, it also makes it difficult to juggle quality conversations when they do happen. Instead, try choosing to connect with only one or two women at a time. Invest in finding someone you might actually be compatible with, and send them a personalized message.

Introduce yourself. Outside of attraction, what did you find interesting about them? Ask questions. Even if it’s tempting to say something unusual to grab her attention, a genuine conversation will benefit you more in the long run.

As a general rule of thumb, avoid saying anything you wouldn’t say in person. Remember that tone is easily misconstrued online. Also, it never hurts to make sure your spelling and grammar is on point before you hit send.

2. Take Your Time

I often hear men say they’d rather meet sooner than later, because it’s easier to determine chemistry in person. While there is truth to this, it doesn’t take into account that women need to feel an overwhelming amount of safety in order to progress a relationship, even if the woman is confident and assertive. If you pressure a woman to move too fast, it will take longer for her to determine if you’re trustworthy.

For that reason, it is in your best interest to move slowly. If she has an opportunity to get to know you, she will feel more comfortable on your first date—which will lead to a much more genuine connection. If you move slowly and build a connection online first, then exchange numbers, and then plan a date she will have plenty of relational equity built up. She’ll feel excited, ready to meet you. That works in your favor when you finally do go on a date.

This isn’t a race. Don’t rush, and don’t skip bases. Wait to ask for her number. Wait to ask her on a date. Yes, there is a chance that you’ll invest time in one woman, only to find out you don’t have chemistry in person. That’s fine. At least you found out under genuine circumstances, not because she felt unsafe.

If you put in the time and effort, it will pay off.

(After all, wouldn’t you rather go on a first date with her anxious and excited to finally get to meet you, rather than feeling self-conscious and nervous that you’re actually a mass murderer?)

3. Make the Most of Your Opportunity

After you’ve spent some time getting to know each other online (and presumably talking on the phone at least a couple times,) pick something to do together. Consider which circumstances will lead to the best initial interaction possible.

In other words, if you only have mornings available this week, but neither of you are morning people, postpone until you’ll both be at your peak. If you’re shy, choose an activity—like bike riding or ceramic painting—over a talking in a coffee shop. If work makes you cranky, don’t meet after 12 hours in the office. (This is not, however, to suggest you should aim for extravagance—which can be just as intimidating on a first date. A simple, casual setting where you can both be genuine is best.)

First impressions matter. Give yourself the best odds of making a great first impression. 

4. Give Second Chances

If the first date was awful, and you’re sure there is no connection, kindly be straightforward at the end of the night. A simple, “It was so nice to meet you, but I think we’re better off as friends,” does the trick nicely. It’s  better to have closure that hurts a little than to never hear from you again.

However, if the date was just okay, consider giving it a second shot—even if you only see the slightest glimmer of hope. Second dates give people a boost in confidence. There’s a good chance you’ll have a much better connection on the second (or even third) date. 

5. Expand Your Horizons

Online dating is a great tool. It builds confidence and connects us to people we would never meet otherwise. However, do not let it limit you. Let’s not forget our grandparent’s stories. Look up from the screen every now and again.  The next time you’re at a coffee shop and you see someone you’re interested in, take a risk and say hello.

These aren’t magic tricks but, rather, guidelines to improve your chances of making an authentic connection. Considering the number of elements that determine compatibility, finding someone who compliments you will take time and persistence. Be patient. If you play your cards right, you’ll set yourself up for greater success.

Guys, what are your tips for women?

I'm a Christian opinion blogger from Southern California. I believe in social justice, the arts, and naptime. You can read more of my writing at, or watch me struggle to make you laugh in 140 characters on twitter, @treeswillclap.

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