I'm 19 and have never been asked out on a date, never been kissed, and never had a boyfriend before. I didn't feel comfortable with myself until my freshman year of college, which could be the reason. I know my worth. I know I am a very funny girl, a smart one, even talented, so why is this still not happening? If my personality is good, it must be my appearance, correct? I have insecurities about my size. I also am a woman of color and it seems all the men I am interested in like, well, white girls. It's really hard being who I am because I feel no one will ever like me. Has anyone even ever had a single crush on me?
In my life, I've had SO many situationships. There was a boy in high school who was a year younger. He seemed to like me a lot, but gave up after I said it was inappropriate to date a younger guy. There's the boy I had a crush on from middle school up until my sophomore year of high school (who never reciprocated my feelings). After starting college, there was a server at the restaurant I started working at after moving to my university. Then there was the boy I met online that following winter break who tried to use me for my body. Pretty enough to have sex with but not pretty enough to date, huh?
Lastly, there was my boss's son, the most gorgeous man I've ever laid my eyes on. If looks could kill, I don't know how many people would be dead right now. I met him once after my boss invited him over (he knew I liked his son and thought I'd be great for him). I had a lot of good conversations with his son that night, but it didn't go anywhere after that. I wish people like his son would go for me, but I am simply not the one people go for. I'm the one they laugh with or at. That's it. How do I maintain happiness and a love life when I don't even love myself because I've been unloved for so many years? When will it be my turn?
Some notes I had after reading your letter:
1. You didn't start feeling confident about yourself until your freshman year of college. That was recent, right? This is all new. You're in a very different place than you were in high school and you're finding your footing.
2. You are young. There are a lot of people who don't date until college (or later). There are a bunch of other young people who have no idea what they're doing – and no idea how to show interest.
3. Someone in high school, the younger guy, did have a very big crush on you. It didn't feel right to pursue, but that crush happened. This is not a "never" situation.
4. You're seeking love, it seems, at a time in life when people are looking to experiment. I'm not saying it's impossible to have a head-over-heels situation right now, but at 19, your peers might not be looking to have big feelings or relationships. They might want fun. Are you open to that? If not, that's OK, but it doesn't mean you're unloveable. It just means they're not ready to love.
5. Your boss's son. Well, the stakes there were pretty high. It's tough to be casual when your dad is literally presenting you to a woman he respects. It might have felt a little too close to home.
I'm so sorry you've had experiences that have made you feel lesser than, or like you're out of the running because of who you are and how you look. All I can say is that there are a ton of people out there. The world is bigger than your boss's son and a workplace crush or two.
I usually love when people try to meet others in real life, but I do wonder whether you might enjoy more swiping on an app, just to meet people who aren't already connected to your life. It makes it easier to move on, and can remind you that there are so many others. (Do that within reason, of course. It should not take much of your time.)
Also, this is a great time to do other things. Getting busy with hobbies, outside of work and homework, might bring you some joy. Eventually, maybe you'll find love that way too.
Readers? Pep talk for a young reader? Also, when you were 19, did people have dates? How did people show interest? Was your experience different?