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Search Results: date a shy guy
Is my affectionate male friend straight or secretly crushing on my bi best friend?
My male best friend is bisexual, and we have a mutual male friend from the improv community. This guy has more female friends than male friends. He talks to women naturally, but with men he seems unable to start a...
Anonymous
(25-29) Which date night outfit should I wear if I’m short and shy about my legs?
I’m short & have blonde hair. With any of these outfits I plan being a crop black jacket over & shoes black flats I’m skinny so I like to cover my legs but fear I won’t like the tube dress as guys stare at girls that...
Anonymous
(25-29) 
How long should I wait until I ask him to be my boyfriend?
So I met this guy at my senior prom a few weeks ago. He asked for my number, and we've been texting almost every day. I've been on two dates with him, and he gave me one of his hoodies today (I'm wearing it right now)....
FizzleMyPickle
Xper 1 Age: 18 How can I build confidence in dating as a shy, introverted guy?
I am 23 yo male and i had one relationship, we were young and it all was kinda awkward. Since then nothing. The truth is i am kinda picky. Few years ago there was one girl i really liked, things were going well but then...
Anonymous
(25-29) Does this girl’s teasing and attention mean she has a crush on me?
I recently joined a new group that is male and female of all different ages. This girl very early on makes faces at me and she seems to never shy away from talking to me, even when she is busy. We text occasionally but...
ChaseBee
Xper 3 Age: 37 Where and how did you meet your partner when dating felt impossible?
I am 24yo single guy. I am introvert and a bit shy but i can be extroverted aswell, i just like spending some time alone. Dating has always been tough for me. People tell me they thought i would be the first one to get...
Anonymous
(25-29) How do I stop wanting romantic validation and accept being single?
So, as the title says, I am a girl who clearly struggles to date. I am 20 and I have never been asked out, almost never experienced catcalling, my dms are also basically dry and non existent. Its obvious that I am no guys...
Anonymous
(18-24) I feel awful about what happened with the guy I was dating. Did he lie all along or was he just avoidant?
I was dating a guy for a few weeks and had been on a couple of dates. Things were slow paced but I figured from what he explained as wanting to build an emotional connection first, that this would obviously build up...
Anonymous
(30-35) Am I screwed when it comes to dating?
if I'm a shy girl with terribly low self esteem who struggles to talk to guys? no guys ever ask me out or hit on me. obviously going to bars isn't gonna work... so how the hell do i get a date? its really hard to hit on a...
Anonymous
(25-29) Is it ok if I initiate a kiss or is that too forward?
I know this a different time period. Normally "guy kisses girl." My question is if at the end of the night on a first date is it ok for me to initiate a kiss or will a guy not like that. Will this run guys off? It is not...
Angelbabylips
Xper 5 Age: 46 I’ve been off and on with this guy, what should I do?
So I have been on 3 dates with him but never alone, always with my friend and his friend. We really clicked and talked but he never knew when to take me seriously cause im always joking and didn’t want to chase that much...
Anonymous
(18-24) When a guy asks a girl out for a date does she immediately think he wants to have sex with her?
If she does then why wouldn't I be shy about asking her?
Anonymous
(30-35) How is it like date a guy with kids? how do you get time to meet&date?
I once met a guy on a dating app. He had a kid he had see Sundays. We met in the car , no date he wanted sex & we shared a drink. I don’t let him have sex. We just madeout. But he wouldn’t text much, no plans for dates,...
Anonymous
(25-29) How easily do you befriend folks from the opposite gender? (More easily than folks from your gender)?
While it's always been easy for me to befriend guys regardless of the social/professional setting, yesterday was a funny little snapshot of how simple and quick it is. Leaving the party scene behind with the dust of 2025...
Need Guys advice: a guy pursued me out of nowhere, he only saw my photos and asked his friends about me. was he interested only in sex?
very weird situation. A guy started texting me and wanting to talk/text etc. but i didint know anything about him, he was very eager to know me, always saying - now i got u, u won't run away and so on playfully, but he...
Anonymous
(36-45) Why can't they understand the reason I prefer bad girls?
Hey, good girls! Yes, I am talking to quiet girls and trad conservative girls! Yeah, you! Guess what? You are boring. As a good decent wholesome MASCULINE male, I prefer bad girls because they are confident, tough, and...
Vividga6
Xper 1 Age: 29 Do you think he likes me?
I met with this guy almost 2 months ago and I can’t forget him and I’m not an obsessive type. I’m 23 years old and he’s 19. We just met to be fuck buddies but he turned out to be a shy and sweet guy. He barely looked at...
Anonymous
(18-24) Do you think he is just (50M) very fond of me or into me (32F)?
He is a colleague. I really can’t understand if he is really fond of me as a person or if he is interested in me romantically but trying to hide or it something. Sometimes I am sure that it is romantic, sometimes I am...
Anonymous
(30-35) Is it my weight? Will it help if?
Hey so I've been seeing this guy for a long time. Lol used to date in the past for a while and started up again but we are very close friends also. Weve expressed our love for each other multiple times and we are always...
hello222444
Xper 3 Age: 35 