Food for Thought

I have seen Will twice more since my last post. We saw each other on Thursday night. He picked me up and we went to the same coffee shop that we had our first date on and tried more of their teas. We even sat in the exact same booth. It was really sweet. He asked me if I wanted to watch a movie with him afterwards and I said sure. We ended up getting a movie at Redbox and watching it at his place. We had the movie on for about five minutes before we started to kiss and then make our way to the bedroom. He is incredibly strong and will always pick me up and I’ll wrap my legs around his waste as he walks us there. I’m pretty small, but he is also very strong.

Things escalated and we were in the same situation as last time. We were both completely undressed and it seemed like sex was what was going to happen. So I asked him if he wanted to, and he replied by asking me if I did. I didn’t really know if I did or not so my response was just to kiss him. He pushed himself into me once and asked if it hurt. I told him it did. He said he’d need to get a condom anyways. He rolled off of me and said, “Can I ask you a question?”. “Sure.” “Are you a virgin?”. I had a feeling that would be the question. I said, “Not technically.” “What do you mean?” “I have done it a couple of times but it was a bad decision.” “A bad position?” “No, a bad decision.”

It was silent for a bit until he said he was sorry my first time was bad. I said it was okay it was my own fault. He kissed me on my forehead and said it wasn’t. After this exchange he said he thinks we should wait and I agreed.

I felt so much better after having this conversation since I felt weird about last time. Clearly he didn’t view me as “easy” or “fast” since I felt ready last time. I feel silly now for even thinking so because if you met me you’d know I’m not even remotely like that.

I do feel a bit strange about one thing though. Ever since my horrible experiences with guys since going to college (you can read about in my earlier posts), I feel they have changed my views on intimacy. I used to think that I was the type of person to only be intimate with someone when I really liked them and we were in a relationship. I thought sex was such an incredibly special thing you should only do if you’re in love. I now find that it is hard to live that way in today’s society. I still do feel this way to an extent, but it seems like no one else does. I want sex to be special but it seems that no one else views it that way. But if sex isn’t a big deal and isn’t a beautiful and special thing, then what is? I can’t deal with the idea that I’m having sex with someone and it doesn’t mean much, that is so depressing to me. It’s such a vulnerable thing to do, yet even Will, the guy I’m with now who I think has tremendous integrity and morals, is ready to have sex so early on. Does he not view sex that highly? Or does he just already like me that much? Is it really that old fashioned of me to want to live in a world where we only kiss people we have feelings for and have sex with people we’re in love with? At the very least I want to be in a relationship with him before we have sex, but I’m leaving that ball in his court. We haven’t had the talk about it yet, and I’m not really sure how/when that will happen. I don’t really know how long people typically wait to define their relationships these days.

It seems like next time I’ll have to tell him I want to wait on sex for awhile. I am not really sure how long I even want to wait to be honest. But I do know I want it to be special and no one ever regrets waiting and taking things slow. I really like him so I don’t want to rush into things this time and have regrets. My first time was a huge mistake that I want to start with a clean slate and make this time as special as I’ve always imagined. (or at least close).


Will Update

I’ve been dating Will for several weeks now. It’s been extremely picturesque thus far.

He’s unlike any guy I have ever dated. As opposed to showing red flags he’s been showing green flags. He continues to surprise me with how great he is. I also already knew he was a stand up guy since he’s one of my brother’s closet friends.

We had gone on three dates that all went very well. The third date we had our first kiss before I left.

We had our fourth date last night. I went over to his place for the first time and we made a lasagna together and made ice cream sundaes. He gave me a beautiful vase of flowers that he had handpicked for me that day.

Things escalated after dinner. We kissed for awhile and he started to touch me. I was surprised how forward he was being but I didn’t mind. He fingered me and it felt amazing. I’ve never had a guy touch me as well as he did. We ended up moving into his bedroom and both gradually got undressed.

At one point he was on top of me and it almost seemed like he was about to start having sex with me. I wasn’t sure if I wanted to do that yet since we haven’t been seeing each other that long but it felt so right in the moment. So I asked him if he had a condom. He replied, “No, w’re not having sex. That’s a bad idea.”

I was caught off guard, not sure if he was saying it was a bad idea because he didn’t have a condom, or if it was too early for us to have sex or maybe he is even saving sex until marriage. (Since he is religious). But since things had already escalated so much I didn’t think it was that bizarre of a concept. I’m totally okay with waiting, in fact it’s probably for the better, I just feel very weird about that exchange now. I wonder if he thinks badly of me now for even suggesting it so early on. The situation is kind of awkward and I really hope it doesn’t ruin what we have because beyond that things are going so well.

Although I was taken aback by his comment we did keep going and I finished him off by hand. We didn’t have oral sex either which I was glad because I’m not a huge fan.

He texted me that night once I got home saying “Thank you for coming over tonight, Scarlett. I had a lot of fun!” I said, “Me too! Thank you for having me.” He said “You’re welcome anytime”. I then thanked him again for the beautiful flowers and he answered this morning saying, “You’re welcome Scarlett. I’m glad you like them.”

We had planned last night to see each other again next weekend to get brunch. I wish we were seeing each other sooner but I think it’s because I’m starting summer classes this week so he assumed I’d be busy.

Most guys probably wouldn’t be turned away by this but he’s not most guys. He’s really classy and wants to build a relationship. So I just hope he doesn’t get the wrong idea about me for saying that. I just feel kind of slutty. I am surprised that I even said that cause I knew it was too soon it just felt like that’s what was happening in the moment and at that second I was okay with it.


It’s a stormy day out right now as I write this. I feel such deep pain right now and naive to let boy troubles get me so worked up.

The guy I mentioned last post, Will, (my brother’s best friend who I have feelings for), asked me out last week. We planned to do something on Friday (two days from today). I was worried on when I should tell my brother, anxious he would be upset. Little did I know that would be the least of my concerns.

This past weekend a friend of mine named Stephen passed away. He lost the battle to drug addiction. He was such a wonderful person, only twenty years old.

To makes things even worse my mom came into my bedroom a few nights later to tell me that Will’s sister killed herself. She told me that he also had asked my brother if he would be okay with him talking to me. My brother didn’t care at all, saying he liked Will and he liked me so he’d be happy for us.  I don’t know why my mom felt the need to tell me that at this point because it seemed to be so insignificant now. Their family is such a wonderful, loving and kind hearted family. They have so many siblings and I can’t even begin to imagine what they are going through right now.

My family is good friends with their family and went to see them the next day. I was so upset I couldn’t get myself to go. I cried all day and felt so depressed. None of my friends understand mental illness. I feel as though I can’t talk to them about the concerns and agony I feel because they have no idea what it is like. I felt bad not going to see Will and felt I should at least text him giving my condolences but I didn’t know what to say. He ended up texting me that day to say “Your brother told me about your friend who passed away. I’m really sorry. Let me know if there’s anything I can do.” I can’t believe how kind hearted he is, he was going through so so much more than me yet said that. I felt so guilty for being so sad for myself.

My older brother was diagnosed with schizo-affective disorder bipolar type a year ago. He is like a small shell of what he was before and every blue moon a tiny piece comes back. He went through psychotic episodes that literally damaged his brain. He was hallucinating, had memory loss etc. When you talk to him now it’s almost like you’re talking to a child and he will be twenty five years old this July. He can’t do anything on his own anymore. He’s been living at home with my parents and I, unable to even get out of bed in the morning without one of us waking him.

I can’t help but wonder if he’ll ever live a normal, happy and independent life. Or even worse if he’ll end up like Will’s sister or Stephen and lose the battle to mental illness. What if he’s next?

I have never felt so much pain for how sad life can be, it’s depressed me like never before. For the first time in my life I’ve started to question my faith in God and wonder how he could put these beautiful young souls in such much pain and turmoil as well as their families. None of my friends are religious either, making me feel so alone in this spiritual struggle as well.

Tomorrow is the memorial service for Will’s sister. I am not looking forward to it even remotely but I’ll be there with my family to pay our respects.

My mom asked me today if Will and I’s date was still on for Friday. I couldn’t believe she would say that. That is the least of my concerns right now and I’m sure it is even more so for him.

Please leave any comments on ways to cope through depression, religious doubt, mental illness support etc if you have any experience. I feel like I’m never going to get out of this dark hole I’ve fallen into.

New Chapter

Sorry it has been so long. I was busy with my classes this semester and didn’t have the motivation to write.

I am no longer going to talk about the past for the most part. I have accepted my mistakes, learned from them and don’t want to look back. It took me a very long time to forgive myself but I believe I finally have and can move forward.

I ended the semester about a week or so ago and now am filled with much more free time. It is officially summer break and I feel so motivated to grow. I’ve been growing as a musician, and reading a lot trying to grow my knowledge. I am also trying to grow physically and getting back into playing tennis. All of these motivation has sparked, mainly (as embarrassed as I am to admit), due to a guy. He makes me want to be the best I can be.

I have always secretly had a crush on this guy, but never thought anything would come of it. That is because he is one of my older brother’s best friends. He is three and half (almost four) years older than me. My entire family adores him. Practically everyone that meets him does. He is fairly reserved or shy, but he has almost every attribute I would want in the man I end up with long term.

I saw him two days in a row about a week ago and we really hit it off. He was clearly interested in me. I don’t mean to be presumptuous or conceited, but you can just tell when a guy is into you. The way he looked at me, smiled at me, and gravitated towards me the whole night. I was hoping to exchange numbers by the end of the night but it was getting late and when I wanted to leave we were no longer by each other.

He ended up following me on my Art Instagram (he had already been following my regular one) after the party. My friend who I had brought to the party told me to ‘dm’ him “Thanks for the follow.” She said it’d be an easy way to break the ice, not awkward. I decided to. He didn’t respond until the next day but he said “Absolutely. It was good seeing you last night!”

I was ecstatic. We talked a bit more about the party via dm and pretty soon he gave me his number. We texted for a bit and I asked him if he was going to my brother’s show on Friday and he said he’d be there. So I will see him there (tomorrow)! I let the conversation die after that because I didn’t want to text him too much and scare him away.

I haven’t been able to stop thinking about him since the party. He crosses my mind constantly and my stomach fills with butterflies. I’m also anxious about it because I don’t know when to tell my brother about it since it’s his best friend. Do I tell him if we go on a date? Do I not bother telling him unless it gets serious? I’m so excited and nervous I can’t stop obsessing over the whole thing. He is so different than any other guy I’ve ever dated or had feelings for. He’s the first guy I’ve ever had feelings for that has no red flags. I have yet to find any glaring flaws or character traits that turn me away. Every other guy I’ve liked I’ve had to ignore certain attributes about them and blindly kept seeing them. He’s different. I know it sounds insane but I feel like he could be my soulmate. I know I sound naive but don’t they say that you just know? It seems too good to be true and I’m scared I’m going to screw up my opportunity with him cause I get so nervous around him.

part eight- last time

Before I begin, I’d like to apologize for the two week delay in posting. I’ve been particularly busy the past few weeks.

I saw Nick several more times after that night. We had sex roughly three to four more times, I don’t really remember.

The last night I saw him we went bowling. I hadn’t bowled since my elementary days and didn’t realize people still actually went bowling. It was okay, I was better than I expected. While we were there Mark texted me. He asked what I was doing that night and I told him I was busy. He wanted me to come over when I was done, it didn’t matter how late it was. I told him I probably couldn’t, but the thought lingered in my mind throughout the night.

Nick and I went back to his place after bowling. We ended up stripping down and having sex again. It hurt particularly bad this time. I told him it felt like he was shoving a hard rock inside me. I got dressed and told him I wasn’t feeling well and wanted to leave. He seemed surprised that I’d gotten dressed so quickly and changed himself and walked me outside. He asked if I wanted to get lunch the next coming Monday and I told him maybe, but I knew I didn’t want to and that was the last time I would see him.

I got into my car and texted Mark back. I told him I could come over. He was excited and I headed over and spent the night. I remember when I got there Mark noticed how nice I looked and asked where I came from. I avoided the question, not wanting to tell him I was just on a date.

I saw Mark a few more times after this, but shortly stopped. He still contacts me every few months to this day trying to hookup. I’ve blocked him on all platforms.

That was the last time I saw Nick. He asked me to go out the week after and I pushed it off telling him I wanted to focus on finals. He got the hint that I was no longer interested and I never heard from him again.


part seven- date three with Nick

It was March 31st, and I had dinner plans with my best friend Alyson. We both had birthdays within the last week and were celebrating together with a birthday dinner. Alyson was extremely boy crazy. Once she had gotten Tinder that year, it was just one guy after another. She ended up losing her virginity to a guy she had just met in a frat house. She was so obsessed with this guy and in the back of my mind I felt horrible for her. He ended up sleeping with her roughly three times and then telling her he didn’t want a relationship. The reason I never slept with Mark was because I wanted my virginity to be special. I had told Mark I wasn’t going to have sex with him unless we were in a relationship and his response was, “Well, that changes things. Oh well, I like what we have now.” I grew up in a very religious household. My parents didn’t necessarily raise me to wait until marriage, but to wait until I’m engaged or at least in a pretty serious relationship.

This freshman year of mine in which all of these things happened, I was going through a rough time. My uncle had stage three liver cancer and moved into our home until he was inevitably going to die. My oldest brother was going through a series of psychotic episodes cycling through different mental hospitals and eventually was diagnosed with schizoaffective disorder. This all put tremendous stress on my parents so my family environment was very tense. I also hated my major in college and was struggling just to pass some of my classes. I suppose all these ways of me acting out of my typical norms was my way of coping with all that was happening in my life at the time.

I told Alyson while we were at dinner that I thought I was going to have sex with Nick. I told her I was seeing him that night and it was probably going to happen. I wanted to know what her experience was like so I knew what to expect. She told me that she bled a ton and it hurt pretty bad at first. But every time after that it hurt less and less.

I also remember her saying, “Are you sure about this?” And I was taken a back a bit due to her past promiscuous experiences with the guys. I told her I was, I just wanted to get it over with. In the back of my mind, I was afraid of being a virgin too much longer. I didn’t want to miss the chance and then be old and still a virgin. She said to me, “Okay, I just don’t think people change their minds that quickly. Not on something like this, it was kind of a big deal to you.” I knew she was right, but I brushed it off. It came to my mind that I didn’t want to be in a relationship with Nick. I didn’t really like him enough. I asked Alyson if it would be wrong to kind of use him for sex with that intention. She said that was horrible and I needed to tell him before we had sex that I didn’t want a relationship.

Nick had a concert that night, so I just ended up going over to his place in the late evening and spending the night. I remember I was wearing a pretty spring dress because of the birthday dinner celebration with Alyson. Nick noticed how nice I looked and thought it was for him. I specifically told him it wasn’t.

Prior to getting there, he told me he had to run an errand so to come a few minutes later. Once I got there we went to his bedroom. He was wearing all black because of his concert. I was nervous to tell him I didn’t want to have a relationship. I wasn’t sure how to say that exactly. While I was contemplating this he must of read my mind because he asked me, “So are we like, dating?” This was so bizarre to me because it was three dates in (and that’s if you call this late night hang out a date) and he already wanted me to be his girlfriend. I had wanted this to happen with Mark for so long and was always too afraid I’d lose him if I brought it up.

“I don’t really want to be in a relationship right now,” was all I said. He seemed surprised and assumed it was just too early and I’d come around eventually.

One thing led to another and it didn’t take long before things started to get hot and heavy. He started off with foreplay on me just using his hand while laying next to me. He wanted to make me finish but failed. He thought he’d gotten close but in reality he really hadn’t. I hated going down on guys. Specifically Nick. Probably because I had no feelings for him nor found him very attractive. It just made it worse. But I did anyways, I don’t know why. I guess I thought you had to in order to have sex. That’s the way he made it seem.

He put a condom on and also had a tube of lube. Apparently that was the errand he had to run. The lube smelled weird and end up giving me a rash down there later on. He started off by pulling me to the edge of the bed with me legs dangling off while I was still laying down. He was standing holding my legs up onto his shoulders. He pushed himself into me and it hurt. I was so determined to just “get my virginity over with” that I didn’t say anything. I wanted him to just keep going, hoping the pain would get better. He didn’t last long and could see I was wincing in pain. He tried a few other positions which were all equally as painful. Thankfully I didn’t bleed a drop though. He never ended up finishing and we went to bed. It didn’t really even feel like I had lost it. Just because a guy pushes his dick into me I’m no longer a virgin? All of a sudden the whole virginity concept felt very strange and adolescent to me.

The next morning when we woke up he started kissing me again. I remember thinking he was way too touchy feely for me. Every chance he got he would kiss or touch me. We ended up trying again that morning. There were times when it didn’t hurt quite as much but it still wasn’t a pleasant experience. The room smelt so gross to me. It smelt like sex combined with that cheap lube he had bought. I think we ended up going to breakfast the next morning but honestly I don’t even remember.

I called my life long best friend Katie that night. She and I went to middle and high school together but she went away to college so I didn’t get to see her as often. I told her I had lost my v card to Nick. It was April Fool’s that day so she thought that I was playing a prank on her at first. I hadn’t even realized it was April Fool’s so I thought that was really funny. I told her I didn’t regret it and it was fine. She said that was good. At the time, I really didn’t regret it. Maybe I had deep down but I didn’t want to deal with more shit going on in my life so I just ignored it.


part six- date two with Nick

Nick asked me out on a second date. It was a little while after our first date since we had spring break as well as busy schedules. We decided to go bowling. I met him at his house again and he drove us to the bowling alley. Once we got there, it turned out it was going to be a forty minute wait for us to bowl. We decided we didn’t even care about bowling much to begin with, so we left.

We weren’t sure what we should do so we sat in his car and checked our phones to see if there was anything going on that night. Nick found a list online of things to do when on a date when you’re unsure of what to do. He saw that one of the things was to kiss. When he said it out loud I laughed slightly, not really wanting to. We kept reading and couldn’t come up with anything to do. After searching he said, “I liked the idea of kissing.” I didn’t say anything and he leaned in and kissed me. It was an awkward angle since we were both sitting in the front of his car so honestly it was a pretty bad kiss. He even commented on how it was pretty bad. In attempt to make up for it he tried again and it was equally as bad. We ended up deciding to just go back to his place to hang out.

Once we got there we listened to a Kendrick Lamar record while playing foosball. Not to brag, but I’m really good at foosball and ended up beating him, which he was surprised and impressed by.

We sat on the couch afterwards and he started to kiss me again. He wasn’t a very good kisser. It all felt very awkward and forced and I wondered if he felt the same way. I kept trying to stop it without blatantly saying it by getting a sip of water. We ended up going to his bedroom because of his roommate. He sat on the bed and told me to let him know if we were going to fast. I instantly felt anxious because I didn’t want to go any further.

We kissed for awhile and he took my top off. He felt up my chest and commented on how he really liked it. He wanted to go even further but I told him I didn’t want to. I remember him saying, “Come on, Scarlett, you know we’re just going to next time.” So I told him I was a virgin, and he said that made more sense but he was very surprised. I told him I had just been waiting for it to be special and with someone I loved but now I wasn’t so sure. He told me it was overrated to make your first time that important.

It was getting really late at this point so I just ended up spending the night. I lived at home and it was almost thirty minutes away and I was too tired to drive. Whenever I spent the night at a guy’s place I told my parents I was with Alyson. They never doubted it.

The next morning Nick took me out for breakfast which was nice. I was so used to spending the night at Mark’s and sneaking out the door with barely a goodbye while he still laid in bed all the day. The most Mark would do was ask me for money so he could go buy Chick fil a for himself.

When I thought of Nick in comparison to Mark it seemed so much healthier and more like what I wanted in a relationship. I still didn’t feel any sort of feelings for him though. But since things were already progressing rather quickly it crossed my mind that maybe he should be the one I lose my virginity to. I was so tired of having to tell guys I was a virgin and just wanted to get it over with. I assumed it would hurt the first time but once that was done sex would just be normal. Maybe Nick was right, maybe who you lose your virginity to doesn’t matter. Maybe it’s better to lose it to him than someone I love because I won’t have to worry about being attached just because we’ve had sex. Is/should your virginity be such a big deal? Would I end up regretting it since my whole life I’ve always viewed it as such a sacred thing?