Being Single in Your Late 20’s

So, for those who read here regularly, or for those just tuning in today… I am 28 years old and I am single. Whew, writing out those words was a bit tough and a bit of a blow. I don’t think I have actually written those onto paper (the online kind) in a while. I am doing a bit more of a heartfelt, and honestly, a post that I have prolonged for so long. Sometimes, we (by we, I really mean myself) tend to prolong things that are the hardest to write or the easiest to cast aside, and we put those fluffy pieces in place. So, today I am going to share what it feels like to be single in your late 20’s, and to date in your late 20’s as well. While I know so many people say I am so “young” and I have so much “time”… I would like to shy away from these connotations today and focus on the truth behind singleness at an age when it becomes tough to absorb.

It Can Get VERY Lonely

I tend to consider myself very much of a social butterfly, a person who has no issue making friends or starting conversations. While I have a good, core group of friends, I attend events regularly, and I enjoy going out… my life still feels like it is missing something at times.
As the world around me keeps moving: friends get engaged, I attend countless weddings (single), I buy endless baby shower gifts… I cannot help but address that ever-present question: When is it my time? I think the loneliest part for me is watching friends have that support system, that backbone, that person to run home to and tell all their happiest moments… or even their darkest. While discussing these moments with friends or family can be nice, I always have to wonder what it is like to confide in a person who is there day in and day out. How can that level of trust be so easily attainable for some, but so tough for someone like myself?
That idea of trust and partnership becomes even more tough when there are countless events, weddings, and family gatherings, and you continually arrive solo. There are only so many times I can invite my friends and cover up the fact that I am still single, and still reeling in that singleness a bit.

Become Independent

So, this is obviously the complete opposite of what was discussed above, but I think this is so crucial to discuss with women of any age who are single. For so many years I relied on people for my happiness, my money, and my sense of living. Overcoming that reliance and finding independence is how I have begun to embrace myself and really learn who I am as an individual.
For me, becoming independent really started when I began traveling in my early 20’s. I lived with my parents up until the day I packed up and left for college. I spent my entire sophomore year and part of my junior year living with roommates and figuring out that balance. After I moved abroad at the age of 20, I never had a roommate moving forward… and I imagine it will be a tough transition if I ever make the choice again. For the better part of my adult life, I have lived alone. That means hanging pictures, fixing light bulbs, fixing my toilet, and becoming my only source of income. Learning to take care of yourself and your own place is one of the most liberating endeavors. It truly changes you as a person, and as a single female.
There are so many times where I see my friends living with their significant other, and while I am envious in a way… a lot of that envy currently stems from wishing I had someone to split rent with. I have become so self-reliant, that making my own money and running my own business has allowed for me to truly figure out life as a single female.

Choose the Relationship With Yourself First 

I cannot stress this one enough! I am SO guilty of not doing this and spent most of my 20’s finding ways to rely on men for a variety of things. I sought validation from men for such a long time: whether it was just a simple compliment, a good morning, or someone to lean on, my life became entangled in the idea of just having that significant other.
I really attribute a lot of the success with “finding myself” and owning my own weirdness to blogging. It was not until I met such fierce women who do this solo, women who have built empires alone, that I realized the woman that I am becoming. I started dressing my body at my current (and fluctuating) weight and embracing what I look like each SEPARATE day. I learned that some days I will look ugly, tired, bloated… but embracing all of that is what brought me my own sense of confidence. I am chubby, thick, fat, curvy, or whatever you choose to call me… but I embrace all of them equally and have learned that those words do not define me or my self-worth. I believe that living alone has taught me to see myself, learn about and fix my quirks, and truly love the person I am and will ultimately become.

Don’t Settle / Trust Your Instincts 

This one goes hand-in-hand with the topic above and is basically just an extension of what was said previously. Loving yourself has taught me that each man that walks into my life needs to be assessed on the value that he can add to the person that I am. This is not to say that men are placed into different categories or tossed aside without regard. Rather, by knowing myself and taking that time to build my own relationship, I know which men are toxic in my life.
I have witnessed far too many of my friends settle into relationships because they felt like they were getting old, or the clock was ticking. I have to be honest, I feel this way almost every single day… but I also know that just choosing any guy is not going to cut it. I have witnessed friends get married and divorced all before I met the elusive “one”. I have friends who have become single parents because of failed relationships that blossomed too early on. By the way, this is no slam to single parents, some of my best friends are rocking it solo and doing a phenomenal job!
There are so many warning signs when dating… and I think we as women get so caught up in the romance and love part, that we ignore potential dangers and threats that can surface with time. I have made SO many mistakes when it comes to men, but most of them are because I did not pay attention to the signs and I just wanted that relationship title and tagline at any cost. Is your happiness and mental health really worth the cost of a cute instagram #couplegoals photo? Always, ALWAYS trust your instincts when it comes to dating and men. If you think there is something off… there almost always is.

I am going to be very real and raw here for a moment and tell you… I have been in some very scary situations with men, some I hope no woman will ever face. So, trust me when I tell you, if it feels wrong, it is WRONG.

Know When to Take a Break

This is my last, and probably most important (they are were) point! I am so guilty of not doing this and not realizing that it was time to call it quits. I cannot thank friends enough for just telling me to literally chill the fuck out and take a break from dating all together.
So here is the truth: I have been on Tinder, Bumble, Plenty of Fish, Coffee Meets Bagel, Match, and I am so sure I am missing some! Online dating is probably one of my biggest regrets when it comes to dating in recent years. While I have met some great people via online dating, nothing solid has ever come out of it… for me at least. I have had some horrendous, creepy, and even scary experiences with online dating. I have received more unsolicited (I repeat, unsolicited) dick pics (sorry mom) than I can count, and men who have managed to track me down outside of the dating app. This does circle back to knowing when a situation is wrong and feels wrong… but it also lends to learning when enough is enough.
I got to a point (a breaking point if you must) where I knew my friends were sick of hearing about it, I was sick of feeling so emotionally drained, and my life just felt off. I was letting these negative experiences and failed relationships with men overcome the positive life I have strived to build for myself.


My experiences in the dating world are not going to be the same as everyone else. While I know that some women have some amazing experiences, mine have yet to be as life-altering or mind-blowing. So, my dating life is still TBD… but I am happy to share a bit of my pitfalls and vulnerabilities with you!

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  1. 8.24.17
    Pam said:

    I agree, never settle and taking breaks is a must. I know its cliche, but when you least expect it, it will happen 🙂
    Pam xo/ Pam Scalfi♥

  2. 8.24.17
    Katie said:

    You rarely ever write personal pieces and I am so happy that you did. I have been following you for such a long time and it’s so nice to see a personal side of you. I’m in my 30s and still single and you hit the nail on the head with this one.


  3. 8.24.17
    Elise said:

    Denise, I love this post! I feel like I have so much to say, but I will try and keep it brief. I was married in my mid twenties, had a son by 30 and was divorced by 32. I have been divorced now for 8 years and in and out of relationships. One thing I know, is I will never settle. My best GF could have written your first paragraph about going to weddings and baby showers while she was single, she got married at 38 and now has two small babies. We had this very discussion yesterday about this subject. Let me preface this by saying she loves her husband and obviously her children, but she stressed that she wished she enjoyed her singledom more than she had. the world is your oyster right now, enjoy every bit of it. And girl when I say ‘you are still so young’, I mean it!! Girl, YOU ARE STILL SO YOUNG, beautiful and smart and because you are so independent and know to never settle you will end up in an awesome, secure, super successful relationship.

    Wow, I guess that wasn’t very brief!
    It will all happen for you and when it does it will be amazing.

    xx, Elise

  4. 8.24.17
    Debby kramer said:

    Denise, I also love this post. Having been married at 18 for over 25 years, divorced for over 15 years, and a single mom (even while married), I would definitely agree with “don’t settle”. Take time to grow, know yourself, become the person you want to be. Since my divorce, I have not dated. I have a huge range of interests, lots of friends, love traveling. I wouldn’t trade my two children for anything, but wish I had not rushed into marriage, although did wait and complete a college degree while working full-time, before starting a family. I love being single, on my own, and doubt I will ever date, much less be in a relationship. I love my independence and the life I made for myself.

  5. 8.24.17
    Lona said:

    Denise, I love this post so so much! I have been following you for such a long time and it’s so nice to see your personal side. My daughter is 21 so I can see how hard online dating, or just dating in general can be these days. You will find the right one at the right time. My advice is this, never settle down, and find someone who can always make you laugh and makes you a better person.