Hoooooly cow. It should better work, or I'll be royally pissed again.
Don't screw it up, don't screw it up...

So. The chick is perfect age & looks for me. (cute, not a bomb but young-looking for her age (over 25) Just the exact type I like, mmmmmmmmm...yeah).
She's also extremely quiet and reserved, and is kinda dateless, too.
Her problem is psychological issues, somewhat depressed, somewhat unsure and insecure. Extremely SHY.
I have MAJOR problems not to get suddenly stuck during a date. Damn you, awkward silence pauses! She doesn't resist me, but doesn't jump on me either. So far, she mostly agrees with what I say, passively avoids some things (i.e. doesn't let me take pictures with her), but is generally friendly. However, she told me that she's comfortable with me, and lets me kiss her (lightly).
What should I do not to frighten her? I am so unskilled as a boyfriend, after all those years of complete inaction... What do I do? I really wanna make it work.
Big problem is that she rarely picks up the converstation, mostly replies in few words, hesitates, is visibly nervous, etc. I don't even know if she actually likes me? OTOH, she SMS me, and comes to meet me, so it's a good sign!
She has low self-esteem I guess. I mean, negative remarks about her intelligence, appearance, and character. Those are mostly unwarranted, and quite sad to watch. I guess i should try to let her know she's much better than she thinks. Making her smile is difficult, but I try.
Wish me luck. (or maybe it's just another false alert, meh)

She lets you kiss her and all, she doesn't reject you when you try to do things with her - except taking pics, but honestly I would too, some people hate pics of themselves, so for me it's a good sign.



I'd say to take it slow but steady. Most people with low self-esteem are used to be used and dumped, and to face inconsistent behaviour. Like if you plan something, don't change your mind. With time I think she'll get less nervous, when she sees she can trust you. And if she faces negative comments about herself on a regular basis, then yeah, it's still good to say something nice to someone if you truly think what you say.

Don't mind your inexperience, if she is as you described, you have more chances of making her feel at ease if you take things slowly (but not lethal-kind-of-slowly) than if you were of a more agressive nature.

Actually negative remarks come from herself. Quite sad. I mean, she's almost like those 'i-am-so-worthless' weirdos on incelsupport forum. I don't know why she is that way, maybe tyrannical parents or something? I mean, a cute girl at such age with almost no dates at all? Why?
So far so good. My only problem is my own inexperience. Now, I fear I run out of things to suggest to do together. Tried to invite her to my hiking group. She refused, can;t handle long trips. Tried local amusement park - also uncomfortable with that. Etc, etc. Just sitting in park is fine, though.
I think I'll go insane if I try to guess, what going on in her pretty head. Let's just ride the wave and see what comes up!

Sorry, I understood the remarks came from other people. A girl in uni was like this, a girl I befriended, she was shy as hell and never said anything positive about herself (and didn't have a bf till her 23). This lack of sel-esteem can be due to yeah, tyrannical/abusive/mean/paranoid parents, or just a very bad time when growing up (maybe she's been bullied, for example). If she had a very strong complex when hitting teenagehood too (severe acnea, weight problems, etc)... You can't know for sure and you can't really guess, but just don't assume too much about her so far...

If she likes sitting in a park and all, maybe she'd like some nature-oriented activities? Visiting a natural park, a zoo, walking around a lake (I don't know where you're from so it's off the top of my hat). Do you / does she like cooking? Cooking together can be really nice, and it's kind of a no-pressure stuff, it's indoors, and both are free to do whatever they want.

Good luck with her

yeah good luck

Maybe ask her what she'd like to do and do that. If she doesn't really say, then just continue with what you know is fine; like the park and stuff. Eventually she will start to get comfortable with you I think, and then will slowly start being more interested in doing things that she originally said no to due to shyness. This is how I would be. Besides, sitting in a park and watching the world go by with a girl that liked me, sounds pretty friggin awesome to me actually.

Don't worry too much about what she's thinking or you'll start second guessing your second guesses. ;o Just roll with it. She will open up in time, honestly. Take it slow. If you like her, adapt to her pace a bit, and she'll start to get more comfortable in time, I think. That's my opinion.

Complement her (in a non-contrived manner) to let her know you value her and that improve her self-esteem. If you make her feel good about herself, she will become more attracted to you.

i'd watch out with girls like that. shy girls don't tend to operate the same as shy guys. they're like deer. liable to bolt at any second, frightened of just about anything. they can have neurotic fits. etc. shy guys are afraid of initiating sex. shy girls are often scared of the idea of sex itself, as an example.

a friend of mine asked out a shy girl once, and she holds it against him as a grudge. like he'd done something badly wrong, unforgivable. that's the typical attitude of most shy girls, in my experience. a mixture of fear and irrationality.

just be cautious I guess.

I know this will sound a bit mean but you can use her insecurities and low self esteem
to get laid. Don't. let yourself get friend-zoned. You already kissed her so now you have
to escalate with more kissing and touching her. Eventually this will lead to getting laid, but you
are going to have to take it slow.

Oh, and if I had to guess I am pretty sure she likes you. She is a shy-girl so you cant expect her to
be like "normal" non shy women. You are going to have to initiate things if you want her bad enough.

F-ZONE? (sound like a sci-fi title) NOT AGAIN!
The only big problem is that I am inexperienced (read: dumb as rock) in relationships, and have trouble reading & decipehring her reactions, other than that, it goes well.

Thanks for advice, fellow boat riders!

Finally! We tried to do 'it'. And by 'it' I mean 'the couple's exercise'. And by 'couple's exercise' I mean SEX! Being both inexperienced, it was awkward and odd, but still the best I ever had in my life. Did I mention she was so awesomely cute?
Well, it kinda failed for the first time (the same thing about intense urgent hard-ons, followed by sudden dropping-downs), but I hope when I get my anxiety lower, it will be smooth and nice.

Great news to read =)

Wow. Congratulations!

Indeed. This is pretty fantastic. Glad it's going well for you.

I gotta say it: D'awwww.

Wonderful! Maybe the two of you can heal one another.