The Ultimate Guide to Dating Love + Sex Love Advice

Here’s why your single friend always gives the best relationship advice

Not to toot my own horn, but I think I give excellent dating advice. However, if you were to ask me for my dating credentials, I would hand you a blank piece of paper.

For some, being serially single is not a choice. But for me, it’s a lifestyle.

I have been single for all of my adult life, and I thoroughly enjoy the independence and solitude—which I know freaks people out. While some single people date, I do not.

So how does this make me—and other serially single people—expert at giving dating advice?

Let me let you in on a few secrets of the trade.

The first secret is not actually a secret but a well-known fact: Almost all forms of content are about love.

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Even content that exists outside of traditional romance genres usually includes love and sex. For example, that action movie you just watched, was there a romantic arc in it?


Most movies, television shows, and books have provided blueprints for all kinds of relationships. A lot of these blueprints have helped me understand what healthy and unhealthy relationships look like.

I’ve also read more than a fair share of fanfiction. Honestly, when you asked for my dating credentials, I could have sent you the link to AO3 and, if you’ve ever read any fanfiction, you’d have immediately understood why this gives me so much credible dating insight.

Even being someone who grew up alongside the Internet has made many of us mini experts on random topics. Most of us didn’t necessarily seek this information out; it just appeared on our Tumblr, Twitter, or Instagram feeds.

Here’s the real secret: All relationships are the same.

Whether platonic or romantic, open or closed, monogamous or polyamorous, all relationships are made of the same ingredients. The dictionary definition of relationship describes the connection between people. And we all have experience with that. I may not date, but I do have lots of friends.

Some of my friendships have failed while others have thrived. This has helped me gain insight on communication, boundaries, and respect—insight that applies to both platonic and romantic relationships.

I’ve also watched most of my loved ones experience all kinds of different relationships. As you can imagine, being single gives those of us who are serially single plenty of free time to observe other people’s relationships—and, if you’re a Virgo like me, judge these relationships in order to perfect the advice we give to those who may (or may not) ask.

Just because your single friends haven’t dated anyone—casually, seriously, or at all—doesn’t mean we’re not familiar with the territory. All of our observations add to our dating advice credentials.

In fact, we’re kind of like therapists.

Because we’re removed from romantic situations, we have clarity uncolored by personal bias and experiences.

Most importantly, your serially single friends arguably have the most experience with prioritizing themselves and their needs. This makes us adept at keeping your best interests top of mind if you come to us for romantic advice.

We want you to be yourself and to love who you are. We will encourage you to take the time to learn more about your wants, needs, and goals before diving further into romance.

The best advice I can give as a serially single person is to try out being single. Being single has a lot of perks, the top of which is that it can give you the time, space, and energy to explore you who are.

I’m not saying everyone should be single. I’m just saying don’t knock it till you try it.

And, don’t worry. I promise I won’t say “I told you so” when you realize being single helped you become a better romantic partner.

Happy dating!

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Love + Sex Love Life Stories

I didn’t have my first real boyfriend until I was 25 years old

When I met my current partner, Mark, at 25, I had been single my entire life. I had dated around casually and definitely had my heart broken a few times, but I had never been in a real, serious partnership. 

I had basically become an expert at being single. 

I knew the exact cues to leave a couple alone if I were third or fifth wheeling (which happened a lot). I knew how to position myself in the group photo so as not to come between any of the couples but also not look like the single loser friend. I had completely detached myself emotionally from Valentine’s Day – it was an opportunity for half priced chocolate and only an opportunity for half priced chocolate. 

I don’t really have a great answer as to why my first relationship didn’t happen until I was 25, other than it just didn’t.

People love to question why single people are single. They also love to assume that it’s a problem that needs to be fixed. 

For me, it wasn’t. 

Don’t get me wrong, there were definitely times in high school or college when I wanted a boyfriend very badly, but eventually, I grew to appreciate all the benefits of being on my own.

It sounds cliche, but I truly did get to know myself in those years. I made decisions that I might not have had I been in a serious relationship (like my move to New York City); decisions that helped me to grow leaps and bounds. 

Without a partner, my friends and family took up the entirety of my heart. 

I went on vacations with my friends’ families and my own parents became equally close with my friends. When my best friend starting dating her boyfriend (now fiance), we all went out to dinner with my parents so they could meet him. 

They love him and are probably about as excited about their wedding as they are for my sister’s.

Because of these relationships I had built, adding a partner into the mix proved to be a bit of a balancing act. Mark fit in seamlessly with my friends and family, but making space for him in my emotional life was a completely new and seriously enlightening process.

Single-ness is a hard thing to unlearn – especially when you’ve been doing it for a quarter of a century, and it didn’t take me long to realize that there was a serious learning curve when it came to being a partner. 

About month or two into my relationship, I was having a bit of trouble with a friend. 

This person had done something that upset me and I confronted them about it, and it made things uncomfortable between us. The whole thing was making me feel kind of sad and weird, but I didn’t mention anything about it to Mark at first.

It wasn’t that I was trying to keep anything from him – it actually just didn’t occur to me. 

Why should he be bothered with something that had nothing to do with him? It wasn’t that huge of a deal, and I could handle it on my own. 

A week or two later when I was feeling particularly stressed, I blurted out something about the situation between me and my friend. When Mark asked me why I hadn’t mentioned it before, I told him the truth – I didn’t think it was necessary. 

He wasn’t offended that I didn’t confide in him, but explained that he was there for me and wanted to share my experiences – the good and the bad. 

That moment was the beginning of my understanding of what my relationship – or any relationship – is truly supposed to be about. I started to realize that this person was offering themselves to me in a way that no one else I’d dated ever had, and I’d be an idiot not to trust him.

A little while after this incident, Mark and I had our first real fight. 

My friends and I were planning an upcoming dinner party – something that we did every few months to get everyone from our old improv group together. Historically, it had been a “no significant others” type of situation; not really written in stone, but kind of an unspoken agreement. 

Mark and I were out at a bar one night and I mentioned the dinner party. When he asked if he would be coming with me, I explained that he wasn’t disinvited, per say, but that we just generally didn’t bring boyfriends or girlfriends to this get-together. 

As a person who had been in long-term relationships for the majority of his young adulthood, Mark was confused.

And as a person who had been single their entire lives and relied solely on friends for my social life and emotional support, I was confused by his confusion. 

This led to a difficult, somewhat painful (but very civil) discussion about our relationship and expectations (I’m exhausted and antsy just typing that sentence). I was totally new to conversations like this, and it was uncomfortable and upsetting and confusing. I knew how much I cared for him, but I also was still operating in the headspace of a single person.

 It was suddenly very apparent to me that fully and wholly welcoming Mark into my life was going to result in a lot of changes. 

And that I really wanted to make them. 

It was truly the beginning of seeing him as my partner and realizing how much I wanted him by my side. 

If you’re only going to allow a person into certain aspects of your life, you’re never going to grow past a certain point. All of my previous “relationships” had stopped at this point – they were casual, superficial, removed from any kind of real emotional effort. I wasn’t at all familiar with the protocol for moving past that point.

But I found that once I jumped into my relationship head on, it wasn’t so hard after all. 

In fact, it was pretty damn easy.