Almost 40 and never dated. I need advice

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Almost 40 and never dated. I need advice

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  • Hayley Matthews Hayley Matthews
    DatingAdvice.com
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    Luke Cage
    Luke Cage
    Participant
    October 31, 2019 at 3:49 pm #224457
    Almost 40 and never dated. I need advice

    I need advice from you fine folks.

    I will be 40 soon and something akin to a mid-life crisis is starting to hit hard. I’ve never dated. I’ve never had a girlfriend. I’ve never had sex. I’ve never been in a relationship and I’ve never even told a woman I like her. I don’t understand flirting and ‘having game’ in the sense that they are so vague and vary from person to person that it feels like something I can’t fully understand. With that said, I’ve caught feelings for a female friend I’ve know for awhile. I tried burying these feelings, writing them off as a passing infatuation but it’s been two years and its not going away.

    I’ll just be blunt: I’m scared. I’ve never done this before, my mind just races with all kinds of scenarios and I never tell her anything. She opens up to me and shares her anxiety, her ambitions, her problems, her photos, her joy.

    Luke Cage
    Luke Cage
    Participant
    October 31, 2019 at 3:50 pm #224458

    Recently she poured her heart out to me, telling me her relationship history and how she desires a relationship now but has trouble being outgoing enough to form one. Like I said, I have no experience with this, does this sound like a friend conversation or she is trying to get me to ask her out?

    dashingscorpio
    dashingscorpio
    Participant
    November 5, 2019 at 8:23 am #224667

    “I’ll just be blunt: I’m scared.”
    Why? You have nothing to lose!

    Tell her you have a crush on her and would like to take her on date.
    If she says “no” you’re still just a 40 year old guy who has never had a girlfriend.
    On the other hand if she says “yes” you may be starting down a path which leads to happiness!

    There are two possible reasons why you are where you are.

    1.You are asexual or not really all that into women.

    Most guys during their sexual peak are (driven) to pursue women.
    They may befriend another guy who is doing well with the ladies and learn from him.
    They may consider going after “low hanging fruit” (girls whom they’re not attracted to) just to gain practice/confidence.
    Some guys will even pay to have sex with a prostitute. Strong urges make men find a way!

    2. You have allowed (fear) to rob you of experiencing the joys of dating, sex, love, and relationships.
    You conquer fear by stepping out of your comfort zone. When we change our circumstances change.
    The world may not owe you anything but YOU owe yourself the world!

    Luke Cage
    Luke Cage
    Participant
    November 12, 2019 at 8:25 am #224938

    I wish I was asexual or even gay. It would make eveything so much easier.

    I’m attracted to women for sure, I’ve just always been shy and/or not really interested until I get to know them. There is something terrifying about letting someone know that I like them that just unnerves me.

    Your second point was beautiful though. I keep avoiding her out of fear. I really do have to work up the courage and just say something, let her know that I like her. I think she already knows, I’m just being weird by not trying to pursue her.

    dazednotconfused
    dazednotconfused
    Participant
    November 18, 2019 at 8:15 am #225186

    I think she sees you as a friend

    sera2775
    sera2775
    Participant
    November 20, 2019 at 8:34 pm #225486

    Hi Luke,

    I’m pushing mid 40s and although I have dated a handful of women since I was about 17, they generally finished very quickly and I wasn’t particularly attracted to them. In all cases they initiated a relationship and in case you wondered I’m average looking. This is down to the fact that although I had normal sexual urges I was too anxious – diagnosed with social anxiety – and never thought of myself as someone who would be attractive to another.
    I haven’t dated since 2009 – apart from an embarrassingly short internet thing – and think at times that I never will. I know myself fairly well; but I don’t take myself out of my comfort zone and ask girls out. Therefore, unfortunately, things don’t change in that respect. Things never will until I do take a chance.

    • This reply was modified 3 weeks ago by sera2775 sera2775.