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. 

Love + Sex Love Life Stories

13 things you’ll only understand if you hate dating

If you’re someone who hates emotions, easily feels awkward, finds the idea of being shackled to a significant other panic-inducing, thinks that marriage is a trap, finds mushy couples nauseating, or just generally dislikes dating, I feel you. Dating is hard, especially in 2017, and some of us prefer to keep things lowkey and stick to casual hookups. Some of us don’t even go that far and prefer to have casual wine nights with the same four friends, weekend after weekend because meeting new people is exhausting.

Quite frankly, being in a relationship seems way too demanding for me. Relationships drain me and take up precious time I could be using to see my friends, explore new cities, research important social issues, and sleep. I’m not a particularly warm person, and I can admit that I have little interest in romance (gag) or PDA.

If you also find yourself emotionally estranged at all times or just really value your freedom, you’ll probably identify with these statements on a deep level.

1. You think flirting is hard

[Image Description: A woman sitting in on a chair, raising her hands while saying, “Maybe I like you, maybe I don’t.”]
I’m a very sarcastic person, so attempting to turn that part of my personality off and actually be nice to someone who is showing interest in me is difficult.

I’m often kinda mean and scare people off, but I can’t really help it.

2. You’re terrified of “catching feelings”

[Image description: A woman with a terrified expression screaming as the camera zooms on her face.]
This is especially true if you’re about as sentimental as a paint chip. Where did these feelings come from? Do I actually genuinely care about someone other than myself? How do I stop this?

3. You dread having the “What are we?” conversation with your fuck buddy

[Image Description: A woman wearing a dress waving her hands and leaving after giving a flying kiss with both her hands.]
We’re nothing because I’m about the dip-the-fuck-out-and-end-all-contact-with-you approach.

4. Seeing your friends in happy relationships and knowing you’ll never have that is a sad reality check

[Image Description: A sleeping hamster falling in a small hole on his face.]
Do you ever look at happy couples and feel a yearning for a significant other who isn’t a total fuck, only to remember the combination of your debilitating anxiety, tendency to cancel plans and general emotional unavailability that only perpetuates your relationship with wine?

5. Your response to nosy relatives is on point because you’ve said it so many times

[Image Description: A woman saying “Stay out of my business.” to another woman.]
For the umpteenth time, no, I’m not seeing anyone, because I avoid that shit like the plague. Nothing to see here, move along!

6. Listening to your friends’ relationship troubles is lowkey annoying because you just can’t relate

[Image Description: A man in a woman’s wedding gown saying “I know.”]
I want to be there for you, but nobody likes me, so there’s that. I don’t know what it’s like to enjoy being with someone else in the first place, so I probably can’t help you.

7. You make it abundantly clear to all your hookups that you’re NOT looking for anything more

[Image Description: A woman sitting on a sofa saying, “Nah!”]
So they won’t text/snap/slide into your DMs the next day! Be honest from the start so you don’t have to deal with their emotional baggage later.

8. You’re resigned to being the third (or fifth) wheel when you go out with your friends and their partners

[Image Description: A man and woman are holding hands on top of a table, looking at each other, when another woman comes and sits on one of the chairs of the table.]
But at this point, it’s not even weird anymore.

You’re no longer just tagging along; it’s more like you’re a part of a small family. And you’d rather hang out with your friends than a significant other, anyway.

9. You honestly wonder how TF people get married

[Image Description: A man in a pink snapback saying, “The fuck?”]
HOW? How do you decide you want to spend a lifetime with someone? How can you put up with someone else’s annoying habits, day after day, year after year?

I can’t even decide if I like these tacos enough to eat all three.

10. You scoff at the idea of soulmates

[Image Description: A man laughing with a hand over his mouth.]
Lmao, excuse me, what?

Yes, I’m clearly jaded, but also, soulmates aren’t a thing. When people use this term I’m caught between laughing hysterically and vomiting, and sometimes I’m not polite enough to keep this reaction inside.

11. You feel legit nauseated at the prospect of long-term commitments

[Image Description: A woman saying “Everything hurts and I’m dying.” while smiling into the camera.]
Surprise, those aren’t butterflies in your stomach, it’s just your stomach churning.

12. You’re pretty sure that if you ever are married, divorce will absolutely be part of your future

[Image Description: A woman standing with the door of the room half open, saying “I want a divorce.”]
I hate to be super pessimistic, but it’s true. If I get tired of people after dating them for only a few months, how will I survive a marriage?

‘Till death do us part, no thank you.

13. You have constant crushes but know none of them are serious

[Image Description: A woman sitting on a sofa in a red dress smiling while saying “Look, he’s cute!”]
You see attractive people, admire them from afar, but since you’re awkward, you never approach them or make any serious moves. This aggravates your friends to no end, but you’re content to stay in your reclusive bubble.

Will I ever find a life partner? Probably not. Dating simply isn’t enjoyable or worthwhile to me.

Plenty of friends and family have told me that I just haven’t met the right person. News flash: men are terrible and I’ll probably never meet one I can stand. But my aversion to dating goes beyond my hatred of the patriarchy.

I genuinely value time to myself. I don’t see anything wrong with going through life without a partner; in fact, traveling, living, and making life changes by yourself can be incredibly fulfilling and even relaxing.

If you’re like me and dating isn’t for you, don’t let anyone tell you that it should be. Keep doing what you’re comfortable with and living your best life.

Love + Sex Love Life Stories

I have a major secret about my love life

My social media feed is full to the brim of articles about things only newly single people will understand or the best techniques to mend your heart after a breakup. While I can vouch that eating chocolate and ice cream is comforting, I don’t relate to the relationship advice given, because I’ve never had a boyfriend.

I haven’t achieved the life milestone that the majority of women my age passed in their pre-teens. For the longest time, I believed this made me strange, and it damaged my confidence and self-esteem.

I started to feel the pressure to be in a relationship, even at a young age. I’ve always noticed and had crushes on boys from school. It’s a rite of passage for a typical schoolgirl.

But those crushes never really went anywhere.

As I progressed through primary school to secondary school, there was a stark difference between those who had a boyfriend and those who hadn’t. The ones who did were confident and mature and everyone envied them. Including me.

Of course, I was jealous. I was 16, and I’d never had my first kiss or a boyfriend.

When it came to family interrogations, I avoided conversations about boyfriends and ‘having my eye on anyone’ like the plague. It’s one thing having my friends know I am forever single, but to have my family know was twice as embarrassing.

For the next two years, I struggled to progress any friendship into something romantic. I was out of luck. It wasn’t until I discovered Tinder in my first year of university that I found my chance to date and possibly find a suitable boyfriend.

My first date with a guy from Tinder was going well until he asked about previous relationships. My body froze. I had two options, pretend I had a long line of ex-boyfriends or admit I had never been in a relationship before.

I chose the latter.

He was taken aback by the response and fired questions about being single for so long. I wanted the ground to swallow me whole as I tried to defend myself for not being in a relationship.

After the date blunder, it came to a point when I was no longer having fun on dates and meeting new people. The irrational fear of having to reveal that I’d never had a boyfriend was starting to have an impact on my self-confidence. I believed I wasn’t good enough for anyone.

I’d had enough of trying to find a boyfriend. It was impossible because it doesn’t just happen overnight. In order to combat the unrealistic ideal of finding love, I deleted Tinder and stopped trying to rush into a relationship.

And it worked. The time I had spent swiping left and right and talking to guys I wasn’t interested in was used more wisely. I was a lot happier and even my grades were better.

In that time I realized there’s not a time limit to achieve a milestone of having your first boyfriend. Now I sleep peacefully knowing it is not the be end and end all. It doesn’t matter when it happens because there’s no rush. I may have a boyfriend in the next week, month or year.

I may still be single and writing down my feelings about my non-existent love life.

And if I am still single and not ready to mingle, I will remind myself that it’s ok not to have a boyfriend.