GravyTrain over on our forums asked this question:

Hey bro I had a question about this.

You talked about that little feeling where you care about the other dudes she’s fucked. Even if there’s no lovey dovey shit going on, I still think about it, like IE: Has she gotten railed out way harder, bigger dick, more attractive dudes, AM I GOOD ENOUGH OR AM I THE BEST, IS SHE LYING when she says I’m the shit etc…

You said get over that with exposure therapy. I see that. But I feel like that would make it worse before it gets better?

Can you walk me thru exactly how to do this? I definitely have that issue. I want to be the BEST a chick has been with and I know for a fact that’s not possible and I should not care. But I do.


This is a question I’ve gotten a lot; and it’s something myself and every single one of my mates has had to go through. I’d wager a bet that 99% of guys worry about being the best a girl has had, and it manifests in all sorts of different ways. Stressing about not being able to make a girl orgasm – “I bet other guys in her past could make her cum.” Stressing about not being muscular enough – “I bet other guys in her past were buffer and leaner than me.” Stressing about not having your shit together – “I bet the other guys she dates have way more money than I do.”

This stuff really used to eat away at me early on, when I hadn’t gotten laid as much as I have now. Or put another way: when I was more insecure and less confident about my sexual abilities. I doubted my own abilities (because I didn’t have a lot of experience/practice), and so of course I knew I probably wasn’t the best she’d ever had.

You know what fixes it? Practice. Your insecurities/worries about being the best go away once you’ve gotten decent at sex and you’re happy with where you’re at. If you own a magic wand, if you’ve read my foreplay guide, if you’ve explored a lot of things from your sexual bucketlist, you’ll eventually start to feel pretty damn confident in your bedroom abilities. If you know you can make a girl cum 10 times in 15 minutes (by cheating and using the magic wand….), if you know you can show her things she’s never tried before, you won’t stress so much about, “Am I the best?” You’ll already know you’re pretty damn good; you won’t care what any other guy is like.

If you’re a little insecure and worry you’re not giving girls a great experience, then just aim to go out and explore more. That can be with multiple women if you like; or with one girl you’re dating. Go read my sexual bucketlist article and brainstorm a bunch of ideas you want to try. Ask your girl(s) to write her own list of things you two can try together, and then have fun exploring everything and practicing.

Essentially, by saying, “I worry I’m not the best a girl has ever had” – you’re saying, “I know I’m not all that great at sex.” Then fix it by getting good at sex. Practice makes perfect; so go practice. You won’t care so much about whether she’s had a bigger dick in the past when you know 50 different sex techniques to blow her mind.

And remember, as with most things I talk about, you’re probably going to suck a bit at the start. That’s perfectly ok. You’re probably going to be insecure about other guys she’s banging/has already banged; that’s ok too. Your insecurities won’t disappear overnight. Just keep working on yourself, keep making progress, and one day none of this will matter so much. One day you’ll wake up and you truly won’t give a shit if you’re the best a girl has had.

And while we’re on the topic of perfectionism, let’s break down the notion of “best a girl has had” for a second. Do you need to be #1 – or is being top 5 good enough? Why is your ego so hardcore-focused on being the absolute best in the whole entire universe; do you really think you’re that special?

I don’t think I’m the best every single girl has had. I’m definitely in the top 3 for most girls. Some girls I’ll be absolutely the best, while other girls I might only be top 3. That’s cool as hell. I don’t need to be the best – because I’m not insecure about my abilities in the bedroom anymore.

It’s ok if other guys are better than me. It’s ok if some other guy has fucked her brains out and given her a better experience than I have. It’s ok if some other guy had a bigger cock than me; mine’s not that big. I don’t really care; because I know I’ll meet some other girl who’ll think I absolutely am the best she’s ever had. I don’t need to be every girl’s best, because on average, I’m in the top 3 most girls have had. That’s alright by me.

Let’s also talk about the fact that neurotically-obsessing about being the best takes you out of the situation and traps you in your own head. A cute girl is naked in your bed, enjoying your company, moaning for you and begging you to fuck her, and all you can think about is some other dude’s dick? She’s right there with you right now, so get out of your head, let the insecurities go – they don’t matter. Have fun with her right now and give it your all, and you’ll often find just by not being so in-your-own-head, you’ll actually give her (and yourself) a better experience because you’re actually being present.

If you want some actionable steps you can take to overcome these insecurities, do what I did: exposure therapy. Yep, you already know what I’m going to say: Start asking girls you date about other guys they’ve slept with/are currently seeing. You don’t have to say, “DID YOUR LAST BOYFRIEND HAVE A BIGGER DICK THAN ME????????????? 🙁 🙁 🙁 🙁 ” You don’t have to scream at her, “I KNOW YOU THINK I’M UGLY COMPARED TO OTHER GUYS YOU’VE FUCKED!!!” then run away crying.

Just casually bring up the subject of exes – “What was your last BF like?”
“Out of all the guys you’ve ever dated or slept with, who was your favourite and why?”
“What qualities do you like in a dude, and what makes a guy the best to you?”
Or, you can volunteer your own info – tell her about your past relationships, what you like in a girl, and then get her to reciprocate.

This is exactly what I did; I started opening up to girls and getting them to open up to me about past exes/guys they were still seeing. I’d ask what they liked about those guys, what they didn’t like, and try to expose myself to the information I was insecure about. It sucks at first (you’ll feel very insecure about what she tells you), but with each new conversation, I found myself less and less terrified of hearing about guys who were “better” than me. Eventually I just stopped caring. Exposure therapy works.

What I found is girls get something different out of each guy they date. One guy they date might have the hugest dick she’s ever had, but maybe he’s a bit of an asshole and doesn’t know how to be honest. Another guy might be the most generous and giving guy she’s ever had, but he doesn’t fuck her all that well. There are so many metrics you can use to define, “The Best”, that it’s essentially a meaningless term.

The best could be:

  • The biggest dick she’s ever had.
  • The best foreplay she’s ever had.
  • The most honest and upfront guy she’s dated.
  • The best at keeping girls around (retention).
  • The guy who’s been the nicest to her and treated her the best.
  • The best mentor (teaching her about the world/offering guidance) she’s ever had.
  • The most exciting guy she’s had.
  • The funniest guy she’s ever had.
  • The most dangerous guy she’s been with.
  • The roughest sex she’s had.
  • Giving her the most number of orgasms she’s ever had.
  • The most gentle sex she’s had, spending hours teasing her.
  • The best psychological sex she’s had (fucking her mind, making her beg, talking dirty to her and stimulating her imagination).
  • The most emotional sex she’s had.
  • The best toys she’s ever tried.
  • Lasting the longest time in bed.
  • The wildest sex she’s had (3somes, rope bondage, etc).

I have a saying – “Other people have a different rulebook to you”; as in, other people have a different set of rules, a different definition of what constitutes “good” or “the best”. So what you personally classify as “the best”, may be totally different to what she counts as “the best”.

Go back and check how many dotpoints I wrote above. With all of those, how the fuck could any one man possibly be the best a girl has had? You can’t possibly be the best at all of those things. No doubt at least one guy from her past is better at one of those metrics than I am or you are. Oh shit, that means we’re not the best! By using such an incredibly vague and wide range of metrics to define “best”, you’re guaranteeing your own failure – you can’t possibly be the best at everything. You’ve basically said “It’s all-or-nothing”; which is a huge fallacy.

You’re not being objective; you’ve set it up so that failing to be the best at any one of the above metrics automatically makes you a failure. What if we use the reverse logic and instead say: succeeding at being the best at any one of the above metrics automatically makes you a winner. Let’s say you suck at everything on that list except you’re incredibly honest and real with her, and you don’t ever bullshit her. Congrats! You’re the most honest guy she’s ever had. You’re the best!

Pick a metric – one you give a shit about or are already decent at – and aim to be the best at it (or, at least top 3). “Honesty” is an easy one; aim to be as honest as you possibly can be, and you’ll probably end up being the most honest guy she’s dated/had sex with (even if you aren’t always perfect with your honesty). Or aim to own the wildest toys she’s ever seen (ropes, blindfolds, etc) and give her experiences she’s never had before. Or learn a bit of BDSM with her and be the kinkiest guy she’s ever met (or at least top 3).

I’ve had girls tell me (when I’ve asked) that I’m not the best at, say, rough degrading sex. Other guys can probably fuck her way harder and rougher than I can; it’s just not something I like to do. I’ve had girls tell me they’ve been with guys with waaaaaaayyyyyyyyyyyyyyy bigger dicks than me. Taller guys than me. More muscular guys than me. Richer guys than me.Who cares; I know I’ll easily be in most girl’s top 3 for BDSM (if not right there are the top). I’ll definitely be in most girl’s top 3 for honesty (if not right at the top). Definitely in the top 3 for mentoring/guidance. I have a million of my own strengths that I’ve acquired through practice; who cares if I’m not always the best at everything, and for every single girl.

You get to set the rulebook. You get to set the metric you measure yourself by. Pick one thing (or a couple of things) you can be awesome at, and work on them, improving yourself a little each day, until you’re confident in your abilities. Then pick a new one and get good at that too. There was once a time where I had no idea how to have sex, let alone do any BDSM, give a girl an orgasm, etc. I had to learn all of this and get good at it with practice; you sure as hell can too.

Eventually, you’ll be well-above-average in a variety of different categories, and you won’t care so much about being “the best she’s ever had”. You’ll be happy with where you are, and you’ll be able to say, “Who knows if I’m the best she’s ever had – I’m probably not. At least not in every single category. But holy shit I’m pretty damn awesome. I like where I’m at.

And the most important point of all: Does it even matter if you’re the best a girl has had? She’s with you right now, spending her time with you, giving her energy to you, having sex with you. She likes you enough and thinks you’re good enough to be with right now. So enjoy the present moment with her, give it your all, fuck her brains out, date her if you two are more serious, spend a bunch of quality time with her and make the most of what you’ve got.

Don’t waste the present by obsessing about her past.