All The Single Ladies

Must be a girl thing Archives

Could you date a guy who still lives with his parents?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Woman Dusting Houseplant

I love Sundays. Generally they are a pretty relaxing day for me. I drink a lot of coffee and write a lot. Sometimes I read and just try to relax. Actually, I am even known to cook a meal or two on Sundays. Another great thing is that Sundays are usually a great day for television, which is where I get to admit to watching some of the really lame shows that I actually watch.

I tend to be drawn to MTV occasionally on the weekends. There is often a marathon of shows like True Life or Made and what can I say, I am a fan of those shows for the most part. Hey it's a little better than my addiction to Teen Mom.

At any rate, earlier today I caught an episode of True Life which was about people who lived at home with their parents. I am pretty sure it's a fairly old episode of the show, but it's one that I hadn't watched before.

On the show there was a guy who was 30-something and still lived with his mom. He openly admitted to being a mama's boy and said he just hadn't had the desire to move out yet. He also openly admitted that he's never had a serious girlfriend and that he thinks it would be a little difficult to bring a lady friend home to his mom's house.

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Date Night Challenge Week 2: The birthday party

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

a young woman sitting on the bed and trying on lingerie

I have finished up the second week of the Date Night Challenge. My birthday was last weekend and there was a big party thrown in my honor. I also spent a lot of time with my mom before the big day because, well, I am her baby and that's what mom's like to do before their baby's big birthday. So that meant I didn't really have time for much dating and there's been a lack of awesome guys to date in my life lately.

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Date Night Challenge from 123Underwear.com: Week 1

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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No, that is not me posing

So the Date Night Challenge from 123Underwear.com is officially underway. Ever since my order arrived last week I have been extremely excited to actually wear what I chose. Yes, they sat in the box because I saved them for an actual date to wear them. After all, that is the point of the Date Night Challenge. Plus, I didn't want to let the newness wear off.

Technically the challenge was supposed to start with a coffee date this past Sunday but the date was rescheduled for last night. And it actually turned into drinks which seems more like a nighttime sort of thing anyway. Plus given all the other events of my weekend I didn't mind having an extra day.

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It's time to talk about (my) underwear

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Young woman putting on tight dress

If you've ever been underwear shopping with me you know that I am kind of picky when it comes to underwear. And when I say picky I don't mean that I have to buy the most expensive things or a specific name brand, I just mean that I tend to only like certain kinds. I definitely try to have some sexy things but I also like to be comfortable. 

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A date shouldn't be treated like a job interview

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Businessman in Meeting

A couple of days ago a reader left an awesome comment on my blog which really made me think. The comment mentioned how a lot of women treat a first date like a job interview which is something that I feel is true. It's something that I will openly admit that I have been guilty of in the past.

Honestly, I wish we could get past this idea that you have to be completely perfect on a date. When I first moved to Chicago, I spent a lot of time dating like that. I have to tell you it honestly wasn't any fun. I mean, one time when I met a guy for drinks the first thing that flew out of my mouth was a comment about how I sweat when I am nervous. Clearly that's not hot in anyway but I also don't think that sort of thing is really that big of a deal. And I am pretty sure that I don't want to date a guy that worries about something silly like that.

I used to beat myself up about things like. And as I was getting ready to meet a new guy I would always go through the list of things that I did wrong on my previous dates. It was exhausting.

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I don't want a guy who needs to be fixed

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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I was chatting with a friend today about dating. He's a friend from Indiana who tends to get annoyed with the whole internet dating thing (hey, don't we all?) so a lot of times that's where our conversations lead.

Sometimes he feels frustrated when he sends a message to a woman and she doesn't respond. Forgive me here because I am paraphrasing since I don't remember the exact way he phrased it but apparently another friend once told him that maybe he's a little too put together. You know, it kind of goes with that idea that women want a man that they can change or fix.

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A relationship should be 50/50

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

close up side view of young man and young woman sharing drink
The other day I was having a conversation with a friend about relationships. I am not sure exactly what I said, but something made him mention that he felt the man should be the dominant one in the relationship. This kind of caught me off guard and I wasn't sure if he was being sarcastic or cute and clever. Turns out that is the way that he genuinely feels and I am not really sure why but that just seems a little strange to me.
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A relationship should be 50/50

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

close up side view of young man and young woman sharing drink
The other day I was having a conversation with a friend about relationships. I am not sure exactly what I said, but something made him mention that he felt the man should be the dominant one in the relationship. This kind of caught me off guard and I wasn't sure if he was being sarcastic or cute and clever. Turns out that is the way that he genuinely feels and I am not really sure why but that just seems a little strange to me.
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Are women too picky?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Couple shopping for jeans

I've been thinking a lot lately about this whole idea that women are too picky. It's not a big secret that people often think women dump men for silly things like wearing white socks with black pants or brown shoes with a black shirt and so on. I've known many women like that and I can admit that there was once a time that I found myself saying things like that when I realized I was losing interest in a guy.

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It's called having sexual confidence

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Fishnet stockings

The other day, I was talking to a friend that I have known for a while. He doesn't live in Chicago so really we mostly trade e-mails back and forth. Occasionally his e-mails involve something to do with my blog since he reads it fairly regularly.

Anyway, we were discussing how some guys choose to approach me when they are "hitting" on me. He advised that I should be aware of my confidence and sexual aura (actually he flat out said to be careful how I use it). And also talked about how I blog about sex so maybe some guys get a certain idea about me.

I am not so sure how I feel about that. Actually, I entertained his ideas for a few moments and then thought to myself are you kidding me?

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In defense of the nice guy

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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For some reason I have been thinking about this whole nice guy thing lately. It could be that Mr. Google
appears to be a pretty freaking nice guy. But then again it could just be that I randomly think about things and then over analyze them to death. After all, that is what I do best as a writer/blogger.

When I was younger, I was way too into bad boys. I mean I was that girl that broke up with guys because they were too nice and then started dating the bad boys. I dated a guy that stole my parents' credit card, there was also a guy that didn't graduate high school and was heavily involved with some highly suspicious entrepreneurs (if you catch my drift). Half the guys I dated didn't have a driver's license because they were in trouble with the law in some fashion.

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We are human beings, not porn stars

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Lovers Undressing

I am going to make somewhat of a confession here - I have been known to enjoy watching an occasional porn or two. And honestly I am not saying that to shock anyone because I think it's a pretty normal and natural kind of thing. Porn can be a pretty fun and even a pretty useful sort of thing, but all too often I think it's easy to forget that porn was also created for entertainment purposes.

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To fling or not to fling (with a 20-year-old)

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Young Man Sleeping in Bed

I've bitched mentioned before that I seem to attract a lot of 20 to 22-year-olds on OkCupid. If you read my blog, you know that I've encountered my share of younger men during my time as a single woman and it's definitely never been a secret that I am not a huge fan.

Honestly, I would like to say that I have some grand explanation for it but the truth is that things between me and the younger fellas just don't tend to work all that well. Nevertheless, I can't deny that some of these younger dudes are super hot which makes flirting with them a whole lot of fun (that is up until the point when they start annoying the crap out of me). And I should also confess that I find myself salivating far more than any grown woman should ever admit, over many guys this age during my commute to and from work each day on the bus (if you follow me on Twitter, you have seen my highly inappropriate tweets on this subject).

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Need to pretend to be committed? There's a ring for that

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

For anyone who is keeping count, we have established that I am not obsessed with marriage but that I want to fall in love. We have also established that I don't think a woman is ever really unmarried but that she can be single at any age. It would only seem fitting that last night while watching MTV, I would discover that someone has decided to make an entire business out of helping women pretend to be committed.

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When does a woman go from being single to unmarried?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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A few days ago I posted about how I am not looking to just get married but to also fall in love. It was a post that was very personal to me and I felt good about it. Well apparently from an article I have seen bouncing around, I need to watch myself because I only have about a decade or so before I move from being single to being unmarried. Honestly, I wasn't even aware that there was a time that women went from being unmarried to single. Clearly you learn something new everyday,

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Woman calls off wedding and refuses to return the ring

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Young Woman Displaying Diamond Ring
The other day I stumbled on an interesting article on Powder Room Talk which talked about what you should do with the ring when calling off an engagement. The article stemmed from a news story about t a woman, named Colette Dipierro from Staten Island, who refused to return a $17,500 ring to her ex-fiance after calling off the wedding.
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Sometimes it's not a deal breaker, it's just down right picky

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

View of a young man picking out shirts from his wardrobe
The other day I was sitting on the bus on my way home from work and there was a girl next to me reading a magazine. I have no idea what magazine it was but there was a section about deal breakers in dating for women.
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