Bros Give Advice for First Timers

I asked a bunch of men, friends and otherwise, to share with me the most important piece of information they wish they had known before having sex for the first time. Here’s what they said:

-The vaginal opening is a lot closer to the anus than you think. Most guys think it’s right up front, like their dicks, but that isn’t the case

-Your expectations probably won’t be met the first time – it’s rarely “magical”

-Try to be in a relationship because it’s easier to say if you’re uncomfortable with something

-If you don’t stimulate her before deep penetration, you’re going to have a bad time

-Foreplay and making out makes sex feel better and last longer – don’t just “stick it in”

-Even if your first time is with someone you’re close to (mine was with a gf at the time) the fact that no one knows what they’re doing just makes it an awkward experience. You can visualize and plan it all you want but there’s no way to imagine that

-Foreplay can matter for the guys too, and girls CAN climax so much that it becomes painful

-It’s never perfect – don’t put pressure on yourself, just have fun and enjoy the ride

-The definition of sex is broader than just penetration, so don’t put so much pressure on that one act

-Try to communicate more with your partners from the start, take everything slow, ask them what they like and be open to criticism

-Take the time to make it meaningful and don’t rush

-Don’t rush it. Make sure you’re ready. It’s OK not to be “in love” but just make sure it’s really what you want

-It really does matter who it’s with and not just something to get over and done with

-Girls are sometimes more worried about themselves than what they think of the guy

-I wish I’d known how to get a girl to have sex with me

-Wear a condom


Online Dating Tips

Online dating has become so popular these days, just about everyone has tried it at some point or other. It has pros and cons, bad stories and good, and each experience is different for everyone.

Many of these sites are what I call a “woman’s market” because most conversations are initiated by men trying to catch the attention of women. As a woman, I can sit back and wait for my inbox to get flooded with messages from all types of men. Having been active on several different sites, I can tell you there are a few things that will either inspire me to reply or convince me I should ignore someone. Here are some tips for men who are inexperienced with online dating, in no particular order.

  • DO have a clear face photo – I won’t reply if I don’t know who I’m talking to
  • DO be clear about what you’re looking for (relationship, casual sex, friendship, etc)
  • DO be honest about your intentions! If you don’t think she’s a good fit after exchanging a few messages, then say so
  • DO use proper grammar/spelling/punctuation because it makes a good impression
  • DO send personalized messages showing you’ve read her profile and share some similar interests
  • DO say something about yourself more compelling than “I like to travel and spend time with friends”
  • DO compliment her and be specific – I’m personally very tired of reading, “nice eyes”
  • DO say what you mean, and mean what you say
  • DON’T insult or berate her if she rejects you – it’s completely her choice and you have to respect that
  • DON’T get into politics or religion right away
  • DON’T message her with “hey” or “what’s up” and expect her to reply
  • DON’T start a conversation with sexual advances, even if that’s your end game
  • DON’T lie about anything!
  • DON’T expect many replies – women are constantly bombarded by messages and often don’t write back if they’re not interestedA Male Perspective

    The above points are all absolutely vital when it comes to online dating – but there are a few more to bear in mind as a man seeking a woman on an online dating site.

    First of all, remember that quality trumps quantity when it comes to messages.  It is better to write one thoughtful, well-considered message a day than to write 100 messages saying, “Hey there.”  Of course, the ability to write a quality message depends largely on the woman’s profile.  Some women will eschew filling out an “about me” section of a profile.  One of the most annoying things a man can encounter when looking at a woman’s profile is that, instead of listing her interests or saying something unique about herself, she tells you to “just ask.”  As if she will be responding to any stupid question any man happens to lob at her.  If you’re a handsome hunk who relies on looks alone to attract women, perhaps you can get away with this.  But if you’re not an Adonis, it’s better to search for profiles that provide actual information about the woman you’re contacting, her likes and dislikes, etc.  With the “just ask” format, you have no common point for starting a conversation.  On the other hand, a profile that makes it clear that a woman likes hockey, for example, will give you a good reference point and an ice-breaker.  If you’re into hockey yourself, you can answer her with questions about favourite teams, playoff odds, etc.  Take the time to find profiles that have obviously had effort put into them.  Personalize your response as best you can.  Remember:  you need to stand out from the other hundred messages any woman is likely to receive on a daily basis.  Don’t be afraid to try different approaches for different women.  The best profiles out there are ones that give you a very clear idea of who the woman is and what she’s looking for, as well as offering clues to her personality.  Say, for example, the woman says she’s interested in poetry – in that case, if you feel up to it, you could try to formulate your response as a poem.  If her profile is witty, try to be witty in your response.  However, remember that you should not try to be something you’re not in order to impress a particular woman.  If she loves sports and you don’t, don’t pretend.  Honesty is greatly appreciated in responses, and a little bit of honesty can go a long way.

    If you can, you should adopt an attitude of never expecting a reply to any given message.  Take the time to artfully craft your response, but don’t feel that you’re entitled to an answer because you took the time.  “Expect the worst, then you can only be pleasantly surprised” – this age old adage holds true in the era of online dating.  Don’t get discouraged if you don’t receive a reply – every woman is different, and while one might ignore an artfully crafted response, the next might respond to one.  Try to show what is unique about you in your response.  Every time you craft an artful reply, you become more skilled at doing so – thus, even unanswered messages are not a waste of time.  If a woman doesn’t respond, do not berate her with additional messages.  Don’t put all your eggs in one basket.  The art of attracting women’s attention through individualized messages takes time to perfect, and one can’t expect to succeed without failing a few times.  Keep your chin up – remember, it’s possible that one of these women could be the “one” for you, and if you see the potential in her profile, but don’t message because you feel discouraged, you will never know what you might have missed out on.

    Lastly, but by no means least – you MUST be respectful of women.  Misogyny is dying a slow, well-deserved death.  Do not think with your penis – lying to get laid is a dirty, dirty trick, and in the end, the truth will come out.  As mentioned above, be honest about your intentions.  The worst that can happen is that you will be refused.  But lying for sex only reinforces the idea that men are generally horndog scumbags.  Don’t be part of the problem – be part of the solution, by showing respect, treating women as you would like to be treated, and not trying to set yourself above them.