Prior to my abrupt move to Los Angeles via Hawaii, I reconnected with a man I met when I first moved back to Honolulu in 2013. In typical 2000s fashion, he sent me a message on OkCupid, but unlike previous “hook ups”, he started the conversation with more than the boring, “hey.” I was instantly smitten by his profile photo and immediately contributed to the budding conversation. We didn’t meet in person for about a month and mostly kept in touch via texts and occasional phone calls. When we finally met in person, we had one of those serendipitous connections I only saw in movies. I asked him to meet me in my car because I felt insecure. I didn’t want our first meeting to include kids teasing me, ignorant comments, etc. that typically happens when I’m in Hawaii. I really liked him and just wanted a chance to get to know him without the everyday garbage of being “different” in Hawaii.
Within two minutes, he leaned over to kiss me. In my 20s, I would’ve been fine with instant gratification. However, this time, I just wanted to get to know him first because I genuinely wanted to get to know him. Instead of telling him the truth and revealing my desire to have more than just another hook-up, I got weird and said something along the lines of, “whoa, I don’t even know if you’re not just here to drug me and steal my kidneys (I had just watched a weird episode of Nip/Tuck). I have a habit of making really intense comments when I feel vulnerable. Some people think it’s funny while “well-adjusted” people think I’m crazy. I’m sure both parties are correct!
We took things very slowly for about another month. Since I only really knew how to be in non-committal partnerships, I often wondered if he was even attracted to me. A few years prior, I met a 20-year-old UCLA student (when I was 25) near his dorm room because I didn’t want him to know where I lived. We seemed to have a nice conversation, but nothing happened. When I arrived home, he sent me a text and told me that he wasn’t attracted to me enough to have sex, but he wanted me to drive back and give him a blowjob. While I do have self-esteem issues, driving from Hollywood back to Westwood was absolutely not going to happen (mostly because gas was so expensive at the time). I can’t remember if I responded or not, but that child pissed me off and I was done with young, socially awkward frat boys).
Eight years later, I still feel weird when a man doesn’t make a move on the first date. Before I met this serendipitous dreamboat, I had never met a man who didn’t try to have sex with me on the first date. As I learned more about dating (reading books like “Why Men Love Bitches”), I started waiting to have sex because men do tend to lose interest (and respect). While all situations are different, there is value in getting to know someone on a deeper level before engaging in sexual stuff. I know I’ve stayed WAY too long in bad relationships because I was too lazy (and afraid) to find someone new.
There are many reasons I’m weird in dating. Some people think I’m a sex addict, but the truth is that I never really learned how to date. I went on my first date when I was 22, much later than most women. I didn’t have the opportunity to make those silly mistakes when I was in high school or undergrad. I felt ugly for most of my life and when I finally met someone who thought I was okay, I took a crash course in finding my sexual identity. While I personally feel that waiting until marriage to have sex is a bad idea, I do agree that one’s first sexual experience will definitely have an impact on one’s sexual identity.
I have another friend who also had sex for the first time at age 22. She waited for different reasons (religion? had comprehensive sex-ed? wasn’t weird?) and her boyfriend create a very special evening for her because he was definitely raised right (and probably cuddled his Mom). He booked a beautiful hotel at a resort in the North Shore and it turned out to be one of the most memorable evenings of her life. When I heard that story, I felt awful because it made me sad for my 22-year-old self because my first time wasn’t quite as nice. I was 30 when she shared her experience and I had finally reached a place in my life where I felt ready to settle down.
When I was 22, I was even more socially awkward than I am now. The first person I had sex with worked across the hall from my office. I was completing one of my mundane tasks and broke their Xerox machine for the 5th time that week. I had met this Sailor (I worked at a Naval Clinic) on my first day. He had gone out of his way to arrange a better parking spot for me and I just thought it was because people in the military had manners (unlike the rest of America!). I remember thinking he was so handsome and kind. …but a man like him would never like someone weird like me.
As he repaired the machine, he asked me if I wanted to see a movie. I almost vomited on the floor from shock. I said, “yeah, that would be cool”. He wrote his number on a post-it and asked me to text my address so he could pick me up after work. In my mind, I thought he was a nice guy who felt sorry for me because I kept breaking everything. I also thought maybe he wanted a new friend since he was in an unfamiliar city. While a VERY small part of me thought that maybe he liked me a little, I didn’t let myself get excited.
He picked me up at exactly 6:00pm and he was super hot. He wore a dress shirt and picked me up in a white Toyota Celica (which was super cool in 2006). We saw Talladega Nights and he grabbed my hand. I was so nervous and perspired so much. It was so bad he had to wipe my sweaty palms on his overpriced denim. He rubbed my back and I was panicking because I didn’t think it was a date. I was zero experienced in the dating department and didn’t want to appear inexperienced at my age. I imagine this is what boy virgins must feel like when they first have sex with a pretty girl. It’s really exciting, yet horrible at the same time.
On the way home, he leaned over and kissed me when he stopped at a traffic light. I had only kissed one other person and had no idea what I was doing. I just followed his rhythm and tried my best not to throw up. When we arrived back at my parent’s place, things escalated quickly. Within five minutes, he gave me my first orgasm by just touching me. Ten minutes later, I was on top of him on the driver’s seat. Was it hot? Kinda, but also really painful. It hurt so bad, but I didn’t want him to know I was a virgin. In the middle of it, I asked him, “uhh, can we do this later?” He saw that I was bleeding and asked me if I was a virgin and I lied. I told him that I just needed to go home because I had to meet friends later (which was true). We made out for a little while and I went home super horrified. As I rode the elevator up to the sixth floor, I was so mad at myself for allowing a stranger to have sex with me without a condom AND bleeding all over a hot guy. I was sure he would never talk to me again and it would be so awkward at work.
I was so surprised that he called me the next day. I had no idea why. I didn’t even call him back right away because I was so nervous. I eventually called him on Sunday in fear of having that inevitable conversation in person at work. He was very sweet and asked to see me again. On our second date, he invited me back to his place and we just talked for a bit before he asked me if we could finish what we started on Friday. I said okay and we had sex again. In the middle of it, I got weird again and asked him, “why do you like me” WHILE he was inside of me. He kissed my neck and said it was because I was “a nice girl”. I bit my lip to stop myself from laughing. As if it wasn’t awkward enough to ask someone mid-sex why they like you, it would’ve just been mean to laugh at such a sweet comment.
We saw each other a few times before I moved to Los Angeles. Two weeks after we started seeing each other, I received an email from his ex-fiancée who had hacked into his email. I received ALL of his e-mail exchanges with about four other women. He had a school girl fetish and asked all of us to wear stockings and Mary Jane shoes. I was too insecure to dress up because I thought he was some kind of pedophile freak and didn’t want to encourage that. The other girls, however, didn’t have a Little Person hang-up and wore their outfits proudly. I was admittedly really angry, mostly because I was so stupid to have unprotected sex with a man who was with a bunch of other women. I was also pissed because I had a lot to do before I moved to LA and now had to get an STI (at the time STD) screening before I left.
Instead of being honest with my feelings, I got crazy with him and told him exactly where to go without thinking about how that would impact him. Yeah, he wasn’t honest about seeing a bunch of girls, but the truth was that I didn’t even ask. I would see him out on the patio frantically trying to explain himself. I felt bad for his main girlfriend because she was so hurt and had reasons to feel deceived. She broke up with him and I’m pretty sure the other girls were pretty upset as well. I, however, enjoyed the intimacy with him and continued to sleep with him until I moved to LA.
Even though it wasn’t a cool thing to do, he later confided that he didn’t have faith in relationships because his fiancée had cheated on him with his friend while he was deployed. At the time, I couldn’t understand how anyone could give up on love because of one horrible person. Now that I’m older, I get it. I was once someone who believed in love and wanted nothing more than to find the love of my life, settle down and raise a family. Along the way, I met people who significantly impacted my perception of relationships and became jaded. I had been non-committal for years because my bad romance conditioning defined me as a person.
The most awesome part of dating someone 25 and younger is that they typically aren’t jaded yet. They have some level of optimism, especially if they’re mature and experienced weird relationships when they were like 15. I’m not so concerned about age at the moment. I really want to find someone who is ready to be in a relationship. Age doesn’t mean a thing because maturity is really rooted in self-awareness and empathy. I don’t know what’s to come, but I do know that I’m looking for a partner, not just someone to fill the space until someone meaningful comes along. I finally feel that I’m ready to be a great partner, mostly because I won’t settle for someone who is just subpar anymore.
Going forward, I will be more honest with my feelings and create clear communication (even if it makes me uncomfortable). I also want to work on:
- Not being afraid if something doesn’t work out. Sometimes people aren’t meant to stay in your life forever, but to guide you to a lesson you’ll need to know for a significant relationship.
- I won’t be so afraid of someone cheating on me. I want to explore dating and find out what I really seek in a partnership (like someone who will be a great father).
- I need to date A LOT! Bring it on hotties!
If you’re in a similar situation or are dating someone weird, let Taylor tell you why it’s hard:
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