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    Home EUROPE Montenegro

    Modern dating has changed, but a professional wingman says these six lessons haven’t

    The Analyst by The Analyst
    May 6, 2026
    in Montenegro
    Modern dating has changed, but a professional wingman says these six lessons haven’t


    Ever since I was a teenager, I’ve enjoyed reading Jake’s column in Glamor magazine. Since 1956, it has been written by various anonymous, single men who have helped numerous women find their way in the dating world, honestly and openly talking about love from a man’s perspective.

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    In 2012, one of the “Jakes” published the book “Always Hit On The Wingman: And 9 Other Secret Rules For Getting The Love Life You Want” (Always Hit On The Wingman: And 9 Other Secret Rules For Getting The Love Life You Want), in which he collected 10 of the most important advice about relationships that he and his predecessors shared with women – and that still apply.

    Usually, when I read books like this, I get the impression that the advice would only work in an ideal world. But as I read Jake’s book, I bookmarked almost every other page to remember his messages. It has become a book that I would love to give to all my female friends – regardless of whether they are single, in a relationship or engaged – because they can all learn something from that collective experience.

    1. Men should not be responsible for your happiness

    My friends and I often said: “If I had a boyfriend, I would be happy”. The problem is that we really believe it, even though we know that only we ourselves can make us truly happy. We can’t shift that huge responsibility to someone else – and what man would want that in the first place?

    Jake describes meeting his ex (who later became his wife): “I realized that she was no longer the same person I broke up with. ‘I thought you were responsible for my happiness – and my unhappiness. That wasn’t fair,’ she told me. I had never seen her so strong and suddenly I wanted to be with her.”

    Conclusion: Learn to be happy alone – then you will become even more attractive, and the right man will be an addition to your life, not its center.

    2. Men don’t think about our bodies the way we do

    Almost every woman has some complaint about her appearance. We are too strict with ourselves – and men don’t like that.

    Jake writes, “Don’t make us feel bad because we like your body… It’s insulting when you tell us we shouldn’t be attracted to you.”

    In other words: if he doesn’t see your “flaws”, it makes no sense for you to emphasize them. Men would “rather caress than analyze”. It’s worth remembering.

    3. Don’t try to be ‘one of the guys’ if you’re not

    One of my partners was delighted when I said I didn’t follow football – he said he was sick of girls pretending to like sports just to impress men.

    Jake has a whole chapter on authenticity: “Girls who like sports or cars are cool. The ones who don’t are, too. But the ones who pretend they are, aren’t.”

    Be yourself. That is the most attractive.

    4. Continue to date others longer than you think you should

    Although I sometimes felt guilty about seeing multiple people at the same time (to be honest with everyone), Jake says it’s actually smart.

    If a man has not yet shown that he wants a serious relationship, why would she close herself off to other options?

    “If there’s even the slightest doubt about his commitment, keep your options open,” Jake writes. “That’s how you tell yourself – and him – that you deserve happiness.”

    5. Even soul mates need space

    In a serious relationship, it is important to maintain individuality: go out with friends, have your own time, not do everything together.

    “Space is power,” says Jake. “The power of knowing you don’t have to share everything with him. A little distance and mystery keeps the attraction going.”

    6. Dating and relationships should be fun

    How many times have we said: “I hate men!” after a bad date or an ignored message?

    Jake reminds: the point of dating is to make it an interesting and fun process. If not – something is wrong.

    “You can view dating as a struggle or as a series of exciting experiences,” he writes. “Love is great – you should enjoy every step”.

    Really well said.

    NOTE: Wingman does not have a direct, natural translation – it is a friend who helps a friend meet a potential partner, in short someone who facilitates dating and flirting.

    The author began her career writing about relationships, dating and pop culture, and later worked in newsrooms such as Women’s Health, Cosmopolitan and others.

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