I have not had a gf since high school, as it says. I have always wanted that fairytale relationship with someone who loves me and I reciprocate.

I feel like time is passing me by and I am missing out on what a relationship could offer. No I don’t mean sex. I want companionship first and foremost. Someone I can confide in and talk with, about all my woes. Someone someday I could see myself having a family with.

I am inexperienced with women. I don’t know all the little things they like, beyond the simple, get the door, pull their chair out, compliments. You know all the chivalrous things society says, are dead. I think I’m a gentleman when it come to treating anyone well.

I know a women from HS and I have “liked” her for quite a while. I just feel like all the normal “do you want to go out sometime?” Would be taken as childish. Granted I could be imagining things. How else would one ask that question? Every time I have pursued someone in the past it has never developed.

So I ask you, where do I begin? All responses are appreciated.

2 comments
  1. I 28M didn’t get the confidence to date until I started lifting, got a skin care prescriptions and found a friend group to go out with.

  2. If you see this person occasionally, ask her if she wants to get coffee. Notice what she wears, did she dress up? Is her vibe too friendly? Does she just see you as just a friend? If you only follow her online, you could certainly ask her to coffee to catch up, if she doesn’t pick up that its a date don’t worry about it, you can ask her out again after to something more ‘date-y’ like a walk in the park (or something physical like mini golf).

    Starting from zero is going to take some time/work, you will need to get comfortable breaking the touch barrier, if someone is on a coffee date across from you for hours then it’s ok to reach out and touch/hold their hand while you are talking, let them pull away if they are uncomfortable.

    If your acquaintance doesn’t work out then you should try making an online dating profile as well, do you know any women that you are close to that can help you pick out pictures and craft a profile? You won’t know what you are doing and whatever profile you make yourself is going to need lots of work if you have never done it before. btw stay away from Tinder.

    You might fall really hard for whoever you first get into a relationship with because you are new to it all, you also might need to try really hard to frame things to yourself like does this person meet what I need/want? what do I actually want in a relationship?

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