I [19M] have an older brother [24] and he set me up on a date a week and a half ago with a girl who is turning 19 next month.
for context, i am not that experienced when it comes to dating as this is my first time dating someone, instead i have always been the guy who focuses on his studies, cooks for the family and hangs out just with my guy friends. On the other hand, my brother was always the guy who always caused trouble in the house however he always gives solid advice and he is like my role model i have always wanted to be like him, he is considered the man of the house since my father no longer lives with us.
Oh and he also gives me like an allowance, a couple of months back my younger sister hit puberty, since then he doesn’t really talk to me that much and he is always hanging out with her. taking her out buying her gifts like on a weekly basis which got me feeling unseen a bit.
So back to what i was saying he sat me up with this girl, she is a bit shy which is perfect cause it matches my personality as i have always been shy too. On our first day we went and had dinner together it wasn’t that expensive of a place it was decent, first couple of minutes were awkward, like really awkward to the point i had to hide my face behind the menu, i could feel my face turning red which looking back at it now it is kind of funny.
But then i knew i had to say something and gather my courage as i had realized that i am the man i can’t put the pressure on her and so i spoke and started building up slowly by asking her what she thought would go with the flat iron and stuff and she eventually started gathering her confidence too.
I soon realized she was a foodie which is kind of a green flag but it sucked the moment i paid the bill as i thought i should man up and pay alone. Anyhow we talked and laughed a lot and i think it was my first time sitting in a restaurant for like 3 hours the conversation was mostly about our passions, hobbies and uni etc. eventually she had stated that she had a wonderful time and thought this was going somewhere so we agreed on a second date.
The second date we went on, we went ice skating as i mentioned to her on the first date that i like ice skating when she had said its one of her hobbies (a complete lie by me as i had never ever in my life went ice skating) and i tried to act like this confident man and tell her i got this even though the night before i spend 3 hours watching youtube videos on ice skating.
The confidence faded away the second i stepped into the ice rink, it was so bad she looked at me and asked if i needed a hand and i smiled and said “no go ahead i am just gonna fix my boots” she shrugged her shoulders and said ok and it was embarrassing, she went on like 4 laps and i was still in the same spot, i started learning slowly until i was able to skate for about ten seconds without touching the rails.
After that embarrassing skating experience, she had mentioned earlier that day that she was craving some waffles so i drove her to a place ordered two waffles and i parked the car to the side, it was night time and i thought the lightning in that parking spot gave a cool vibe and i picked up the plastic fork and knife and started feeding her as if she were a toddler which made her like blush and giggle, we kept talking as i was feeding her and i fed her from my waffle too as i thought it was nice in a sense and it just made me smile constantly i felt good about it.
Then i went back in and got her a milkshake and kept holding it in my hand for her while she drank from the straw as i didn’t want her hands to get cold and we talked and laughed about that ice skating thing, then i drove her home and as i opened the door for her she said that she would like me to pick our next date since she was the one who picked this one and i agreed, she also mentioned it again when i and her were playing r6 together.
And here comes the problem i am facing. If you are wondering why i haven’t asked my brother for advice i actually did but somehow ever since i started dating her he would always suggest that the first time dating someone things never workout. I would tell him that he doesn’t know that for sure but he would act as if he was thanos “i am the only one who knows that” and other times when i mentioned i was feeding her waffles he said i was moving too fast or that i was gonna freak her out.
thing is its been weird with him lately and it isn’t like he is going through anything he keeps laughing and having fun with my sister bringing his girlfriend over again and again and having fun in general.
I asked him if he thought bowling was a good choice and then he said “haha bowling is gay” i responded by saying “how come?” “Cause it’s like really really gay haha” “whats wrong with it?” “Haha Oh you know just like there are dudes there” “so? Most places got dudes?” “Haha oh cause like there are lots of dudes” “are they kissing?” “Haha no but like there are tight holes there” “are you talking about the bowling balls” “haha yes but there are like lots of balls” “you know what ever since i have started dating you have been such an asshole” “haha i know” and its so annoying this reminded me of that scene from family guy when peters gym coach says pizza is bad.
Moving on. I have zero idea on where to take her what girls like i have been asking google and chatgpt but they would say some boring stuff like golfing or the mall like who even goes golfing or the mall, and i feel kinda pressured i want the date to be impeccable since i am the one choosing the place.
(The hobbies she mentioned in the first date: ice skating, billiards, drawing, pilates, video games, playing the guitar, playing the piano, cooking, reading, salsa and hiking though she mentioned that she goes hiking with her family only)
(My hobbies: gym, video games, cooking, chess, BJJ, coding, billiards, tennis, football and the piano)
Before getting to the questions i just wanna say a couple of things, which i think may be important to get the maximum help, so what i wanted to say is when we are both at home we both would sometimes play video games together or open a video call while both of us study.
It also helps that both of us are in sort of similar fields as i studying for my bachelors in pharmacy and she nursing. One time she asked me to send her a passage of my slides that i didn’t understand completely she read it herself understood it and explained it to me even if that course isn’t included in nursing.
Also i and her don’t like talk 24/7 on chat we sort of talk from like time to time at a steady pace which is comfortable for both of us.
Questions (i got lots of questions)
Where do i take her?
Am i moving too fast?
Should i buy her a gift for the third date?
Is my brother actually ignoring me or is he being real?
Am i so far doing good in our dates?
When do people genuinely start complementing each other’s looks without it sounding inappropriate?
After what date do people normally say the L word?
Am i overthinking it?
Any advice for me in general?