Guest Blogger: Dating 101: Do’s and Don’ts by HarleyBangBang

In the winter of 2014, I began my foray into the online dating world. I was resistant to the idea for so long, and kept insisting to my friends that I wanted to meet someone the natural, organic way (don’t we all?). Finally, after months of my friends trying to persuade me, and my own feeling of stagnation in my dating life (read: it was non-existent), I decided to bite the bullet.

I should note that up until then, I really hadn’t dated at all – so the dates that followed were not only my first online dating experiences, but my first real dating experiences period.

I did the online thing on and off for the next two years, and learned a lot. Hindsight is 20/20, and if I only knew then what I know now, I could have saved myself a lot of heartache and tears that were wasted on undeserving boys. Below are some lessons and do’s and don’ts, based on my personal experiences. Would love to get input from you all, and this may very well turn into a multi-part post!

Disclaimer: the lessons below are my own personal thoughts, and others may very well disagree – in the game of love, there is certainly no right or wrong!

If a guy is consistently messaging you, but doesn’t ask you out within the first 2-3 weeks, he is stringing you along. Move on.

This one took me a while to learn, and is a situation that happens way too often to girls in the online dating world. A guy will regularly send messages, ask how your day/weekend was, and engage in flirty banter. But no mention of meeting up for an actual date. Why? Why??? This situation drove me crazy at first, and I couldn’t make sense of it.

After a while, it dawned on me – this guy was stringing me along. He was waiting to see how it worked out with the other 3-10 girls he was chatting up, and was keeping me on the backburner in the meantime. He was being strategic – he didn’t want to put his eggs in one basket, so he was messaging me (and likely others) to keep the lines of communication open. That way, if it didn’t work out with other girls, it wouldn’t look so weird and random to later ask me out.

I can’t say I am necessarily against this tactic. There are only so many hours in a day, and if a guy is seeing other girls, it makes sense to see how it plays out with them before dating a new “batch” of girls.

However, it doesn’t mean that I have to accept being a backup plan. Even the simple act of messaging back and forth takes a lot of time and effort. If it never results in an actual meeting, it’s frankly a waste of my time.

So I made a resolution: if a guy didn’t ask me out within 2-3 weeks of messaging, I would stop responding. In my experience, if no date happened in the first 2 weeks, it was never going to happen anyway. And cutting that dud out of my life meant I now had more time and energy to message new prospects.

Exception: obviously there are one-off circumstances – they are traveling, or give you a reason for being legitimately busy for those few weeks, but make it clear they do want you see you. But barring any exceptional circumstances – after 3 weeks, cut it off. You are no one’s Plan B.

Some of you may be saying, why didn’t YOU ask them out? Fair point. But to be frank, I didn’t want to. Plain and simple. I believe that if a guy really likes you, he will ask you out. I certainly would hint to let them know I was interested (sometimes would throw in a, “Oh we should do that sometime!”, hoping they’d take the bait). But I don’t want to be the one to outright ask for a date. If the guy isn’t asking, it means he’s likely not interested. Again – many of you may disagree, but this approach worked for me and prevented me from chasing after guys who weren’t truly into me.

I don’t like coffee dates.

In theory, coffee dates sound cute and perfect, and low-key enough for a first date. But I realized quickly that there’s a crucial flaw: there’s no natural end to a coffee date.

With drinks or dinner dates (not that I condone dinner dates… more on that below), the server will come by and ask if you want another round or the bill. This provides the perfect opportunity to end a date, because you can politely say you’re tired, and just grab the bill.

Coffee dates, on the other hand, provide no such out. You pay for your coffee at the beginning, and then sit down. I found it supremely awkward to end coffee dates, and never knew how to phrase it. “Okay now, I think we’ve chatted long enough, so I’m going to go home now”—that just sounds awkward.

I usually did a fake look at my watch and said something like, “oh, it’s getting late, I should be heading home” – or sometimes pretended I had plans to get to – but either way, the whole thing felt awkward and too abrupt of an ending. And I’m not even just talking about bad dates – I had some decent coffee dates that went on for a half hour too long, because there’s just no easy way to end a coffee date.

Also, if I finished my beverage before his, I always worried – should I get another one, or just sit there, coffee-less? Getting a new one means waiting in line again – and maybe he didn’t want a second coffee. Also, a second coffee/tea seems excessive. So I usually just sat there, thirsty and praying that he’d chug his coffee down so that I could make up an excuse to go home.

At this point, I’m wondering if the real issue is my tendency to overanalyze… but regardless. Me no likey coffee dates.

I don’t enjoy dates where you walk around.

This is yet another seemingly cute date idea. Walk around the city on a beautiful day, take in the sites and attractions, sit on a park bench and maybe grab an ice cream? How can that not be fun and adorable? Why am I such a killjoy, you might ask?

Personally, I found it hard to properly get to know someone when you’re walking side by side on a first date. “Walk around” dates provide for no eye contact, since you’re naturally supposed to be looking ahead. Which meant that I’d awkwardly keep turning my head every few minutes to look at my date as we engaged in conversation. It honestly was more of a hassle (and strain on my neck) than it was worth. If you’re in a big city like I am, you also deal with crowded streets and periodically having people walk between you and bump into you. Not sexy. Not fun.

And where there’s no particular destination in mind, your conversation is interrupted constantly by “should we turn left or right?” “oh I don’t care, you pick!”. It stifles the natural flow of your chitchat.

And just like with coffee dates, there’s no natural end to these types of dates, so at some point, you have to clumsily say, “okay then, well I’m going to go home now”. Again – me no likey.

Dinner on a first date is risky.

This one seems to be less controversial, so I’ll keep it short: if you don’t click with your date, and you have dinner plans, you are now stuck talking to them and sitting through an entire meal (which you may need to pay for) for 1.5 to 2 hours. God help you if the service is slow.

You have been warned.

If you get to the date first, for God’s sake, grab a table.

I would have thought this would be obvious enough. Apparently not, because I arrived at a coffee date (already a strike 1), about 5 minutes late. The guy I was meeting had gotten there before me. When I got there, I saw (and he certainly must have as well) that it was super crowded. Rather than him using his common sense to snag us a table, he stood there like an idiot in the middle of the coffee shop…

Which led to us walking around in circles until we finally found 2 spots together in a less-than-ideal corner. It was an annoying way to start off the date, and could have easily been avoided if he had simply used his brain.

Note: I’m not saying that because he’s the man, he should have gotten the table for us. Whoever gets to the meeting spot first should get a spot – particularly when you see it’s crowded.

The early stages of dating should be easy. If there’s issues early on, heed the red flag and walk away.

No relationship is without its ups and downs. The older you are, the more issues you will inevitably face, and I am not naïve enough to think the honeymoon stage lasts forever.

However – no matter your age, there always should be a honeymoon phase. I know far too many couples who start having issues (and big issues at that) within the first 1-2 months. I’m no expert, but I refuse to believe that’s normal. And invariably, with all of those same couples, it continued to go downhill and ended badly.

The first few months of any relationship should be fun and lighthearted, with both parties putting their best foot forward. Any problems that exist in the beginning will only grow bigger and bigger; the fights that happen at week 3 will worsen in intensity and severity as time goes on. Lackluster and sporadic texting will become even more lackluster and sporadic. If an SO doesn’t care to impress you and showcase their best side to you at the beginning, they certainly won’t have the motivation to do so later on in the relationship.

Bumps in the road in the early stages are red flags. Heed the red flag, cut your losses and move on, before you’re in too deep.


I fully realize this post may make me sound like a rigid, uptight bi*ch. I swear I’m a lovely person! But I’ve simply dated enough to know what does and doesn’t work for me, and what early warning signs to pay attention to. It’s when I finally started to be firm about what I wanted that my dates started being fruitful.

What are some dating lessons you have learned? Happy to engage in spirited debate in the comments section, or on twitter @harleybangbang. xoxo

For more posts from this amazing blogger please see her site here!

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