Saturday, May 14, 2011

Dating In Your Late 20s SUCKS - Part 1

Going on a first date is always a little awkward.  But dating in your late 20s or early 30s is a whole different animal.

For the record, I'm 27 and single.  I work quite a bit, I'm a book nerd and a music junkie who lives alone in the city with her cat.

Don't judge me.

When you're in High School and College/University dating is fairly simple.  You meet someone in one of your classes, at your part time job or through your ever expanding circle of friends.  There's really no pressure because you're young and even the most serious relationship isn't all that serious when you really think about it.  Your biggest concern is if he thinks your best friend is prettier than you or if you'll appear slutty if you sleep with him too early on.

Dating Post-Grad is a little different.  You're an ADULT now and are more comfortable with yourself, your wants and needs and what you're looking for in a partner.  You're probably figured out what your "type" is by now and are a little bit more conscious of who you date now that you're over the thrill of a cute boy asking you out.

As I mentioned earlier, dating in your late 20s or early 30s is an entirely different animal. 

You've probably had at least one serious or fairly serious relationship by now, which means you've got some baggage.  You've dated enough to know without a doubt what you want and what you refuse to accept in a relationship.  You're probably not looking for something casual and are starting to seriously consider who you're going to spend the rest of your life with.

Dating at this age is a little more political.  You start to think things like "What do I want to get out of this relationship?"  "Do I see myself with this person long-term?"  "Do we want the same things in life?"

What makes things the most difficult about dating at this age is the stereotypes and stigma associated with being single at this age.  Especially for a woman.

If you're almost 30 and single, many people will feel a tinge of pity presuming that if you haven't been able to snag a man by now it's all over for you.  Despite the fact that they may know nothing about you or your life there's that little twinge people get when they hear that you're solo.  And no matter how adamantly you may claim to be comfortable or even happy with that fact, you know deep down inside that they presume you're just kidding yourself and trying to save face.

Cause how could ANYONE be single and be happy about it.

Ok, so I know I'm generalising.  But I'm honestly sick of the look of pity on people's faces when they find out that I'm single.  You know what I mean.  That sad look that says, "Oh you poor dear, can't find a man.  You know you're not getting any younger."  And the sad thing is that many men you meet at this age are going to occasionally jump to the same conclusion.  That you're single for a reason.  And the older you get, the harder it gets. 

I know a few single women in their 30s and many of them have told me that dating at their age means meeting guys that presume they're automatically looking for a husband and God loving those commitment phobic men (kidding) they just run screaming from a bridezilla in the making who's biological clock is ticking.

I remember the first time someone jokingly asked me when I was going to get married.  I was about 22 at the time and currently in a fairly serious relationship.  I was mildly embarrassed but if anything it made me realize that I had no intention of marrying the guy I was dating.  The thing that bothered me so much about it was that I was ONLY 22.  Why were people pressuring me to get married?  I had barely graduated from University.  I was working at my first real job and was still living with my parents.  Does that sound like a person ready to get married?

Now I've had 4 major relationships in my life that each spanned more than a year each.  A few shorter relationships that fell into the less than 1 year category and what seems like a billion first dates.  So it's not like I DON'T date.  I'm just not obsessed with always having a boyfriend.  I'm comfortable with my own company and confident enough about myself and my circumstances to say that I don't NEED a boyfriend.  Not that I'm morally opposed to it or anything.  Not by a long shot.  But I'm not one of those women who defines herself by who she is or in my case isn't dating. 

What I've realized since the end of my last serious relationship is that meeting men at this age isn't as easy as it used to be.  Between work and my friends I don't honestly meet new people all that often.  That goes for men and women.  When I go out, typically I'm with a few friends and that doesn't make for the most approachable situation.  In the corporate world any new people you'd meet are either co-workers or clients and that's generally a big no-no. 

That leaves the grocery store, the gym, online dating and public streets.

I've had a guy pick me up at the grocery store.  He saw me reading a book standing in the cash line and struck up a conversation.  We went on 2 dates.  We had absolutely NOTHING in common and no chemistry at all.

I'm always a little weirded out by people who try to talk to me at the gym.  I guess there's always the theory that you have something in common already if you're both trying to be healthy.  And I guess if he's seen me sweaty, with no make-up on and in my yoga pants and he STILL felt inspired to talk to me that must be a good sign.  But honestly, does this actually happen?  Do people actually meet potential dates at the gym?  Is that why the chick on the elliptical behind me is barely sweating an wearing mascara?

Online dating.  Oh dear God.  Now, I'm not going to completely knock it.  We've all heard the success stories and for busy people it is a logical option.  But I've always found something a little creepy about it.  I tried it once and found it a little awkward and there's always safety/privacy concerns so I'm not inclined to try it again at the moment.

That leaves public streets.  Would you actually go out with a random guy that walked up to you on the street?  Doubtful.

I guess there's always the blind date option but I LOATHE the concept of being a charity case for my happily paired friends.

But if one never meets any new men, how can one possibly find Mr.Right?




  1. You have to do something different! If you stick to the same routine day in and day out, it's gonna be pretty darn hard! I'm also 27 and single (and oh-so-happy about it too!) and I find that I'm meeting guys all the time. You know, what with divorce rates nowadays, all those married folks really don't have all that much to be smug about. Soon enough, WE might just be the smug ones... hehe

  2. Well, are you expecting men to be chivalrous? That is a common problem when women reach their late 20's. Men in their late 20's are fed up with the demands of chivalry.

    Ask men out, pay for their meals. Heck, go dutch on dates. Be independent.

    Finally, it might be you. Ever think about that? Perhaps you have standards that are too high, or a personality that is off the grid. There is nothing wrong with being yourself, but please understand that this could all be your problem.

    I am a man who earns a low income, does not have a college degree and has an anti-social personality, so I know that my dating woes are mostly my fault. Unlike you, I don't have random women approaching me. Enjoy being a woman. It will work in your favor.

    1. Clearly you DO have and anti-social personality because you think this post is in someway helpful or flattering. You have played into the crap notion that we should believe we are screwed up. I've been through therapy and my family has watched my dating life. Everyone concludes I'm actually not screwed up. They have concluded it simply sucks that I haven't found someone yet. But, it is actually no ones fault. I just have not met the man yet that I am willing to compromise my life for. Like Ash, I don't NEED a man. I'm independent and generally happy. I know exactly what I want and I don't care if my standards are high. My standards will bring me happiness. And, I deserve to have high standards! When we were little girls people used to teach us to demand respect, chivalry, to be wooed, and not to settle for a man unworthy of our love. Today, girls and women like me are told to lower our standards, take what we get, and put up with the total crap that men think is 'good enough'. I agree with Ash. I know what I want and I will NOT bend until I find a man that is worthy of my love, patience, and compromise.

    2. Amen to that! No offence, but I'd rather wait a little longer for the right man. Than settle for an anti social who expects me to ask him out and pay for his dinner.

  3. Have you noticed when a man is single the problem is with him? People say, “You need to get out more, or you need to improve your game and learn how to talk to women.”

    But when a woman is single its like, “Ahh well…there’s no decent men left out there.” If a man said that about women he’d be branded a sexist.

    1. I'm not necessarily saying there are no decent men left out there, I'm just saying I have no idea where the heck they are. Mars maybe?

  4. I love this article! I'm 28 and single.

    I think the difficult thing is that nowadays the world is full of activities for couples - theatre, cinema, weekends away. So it isn't easy to enjoy the single life, which is exactly what we should be doing.

    I seek comfort in the fact that lots of my friends are now getting divorced or separating from long term makes me wonder, have we got it right after all. We have our whole lives to be the perfect mother and /or wife. Why not just enjoy surviving in a world of semi-happy couplidom

    Here's to many more cringe-worthy first dates!

    Cheryl x

    1. Thanks! I totally understand where you're comming from on the divorce thing. It seems like all the couples I know are either getting engaged/married, having a baby or getting divorced. It's one extremem to another.

  5. I'm a 30 year old single man and I don't date women over the age of 25 because of articles like this. Too many bad experiences with picky, self-centered and downright mean women.

    1. I will admit to being picky about certain things but I am neither self-centered nor am I mean.

    2. I would actually juxtapose Anonymous' position. I actually will not date women under the age of 25. I'm a 29 year old single male, and I find that the younger crowd to be a big pool of 'want it all' multi-daters who fear commitment. Like the OP, I have a busy life and have tried most of the dating avenues that she skimmed over (the gym, online dating, grocery store pickups) and have found it all ending in frustration. I used to want perfection. Now, I just want someone to come home to that I can smooch all night and call my best friend, and will put up with my neuroticism when it shows up.

    3. Totally agree. The older I get, the more I just want a companion and partner in life. Here's hoping we find it and are aware enough to recognize a good thing when it comes our way regardless of what form it's in.

  6. Was JUST having this conversation with my friend yesterday!! We are both 28, successful in our own rights, confident, know what we want, pretty, educated, and nice! (of course being modest haha), yet.... where the boys at??
    i find they are either scared/emasculated of us, or just want to date us to "get us" and then don't want or know what to do with us after that??
    We both do want to be in relationships, but it is increasingly more difficult and frustrating! How DO people meet one another? Online dating? (i met a douchebag with 12 fingers... nope) bars? (guys wanting to hump n dump... nope) through friends? (date us to "get us" and then...leave.... nope!) work (innapropriate and never been tempted... nope) gym? (who am i kidding i dont go to the gym...nope!)
    girl if you figure somethin out lemme know! haha

    1. 12 fingers? That's hilarious. But yeah, it just seems to get harder and harder.

    2. My favorites have been the cowboy who showed up with his collie in the back of the pickup, spurs, and horse shit covering the bottom of his pants. He took me to Cabellas and tried to by me a hunting bow.

      Another was the hippie who completely LIED on his online account (surprise surprise :/) and showed up to our date with the HUGEST unibrow I have ever seen, incredibly dirty clothes, and a BO stench worse that I have ever experience. He proceeded to tell me that he was currently living in a tent in his parents back yard, only wears shoes on dates, and tried desperately to convince me that dropping out of grad school to run off to the desert to work on his "documentary" was an excellent idea. HELL NO!!!

      Then there was the waiter that picked me up when my girlfriends and I went out for girls night. Super cute, charismatic, efficient, etc. He decided to spend our ENTIRE date telling me stories about how many girls he bangs, his binge drinking, drug use, and how his mother encourages him to bring home trashy girls. Towards the end I had to beg him to take me home. I had slipped away to the bathroom and texted/called EVERY friend I had in the area to come get me. No one answered. He then drove me to HIS freaking house and tried to get me to come inside to "check out his new construction." I got out of the car and walked about a block away without a work calling everyone I knew. FINALLY he came with the car, apologized, and explained that he thought I was "PLAYING the southern belle good girl." WOW!

      Dating sucks after college!!! Hopefully there is another way for all of us. I keep hoping he falls out of plane or something. ugh.

  7. I am turning 27 in a month and I totally feel the same way. I've been out of a 18 month relationship and I will honestly say right now, I don't know what to think. It's quite unfortunate that there are people out there who don't know what they want. That was the problem with my previous one. And like the entry above, I'm also a successful, confident, athletic, adventurous, attractive girl, and that may be intimidating to some. But if your date cannot accept your personality, then it's best they go elsewhere.
    One suggestion from my experience is to make sure your date has the same goals in life. Do they want to be married, or have kids, relocate? What can be overlooked and what is totally unacceptable? One guy I was in a serious relationship with wanted kids, but had terrible grades in college, and became angry at me that I didn't want kids.
    Also, I have noticed that when you're in a relationship, it seems like more people ask you out even if you're walking downtown by yourself. Then when you're single, it seems like everyone is taken. So I guess things happen when you don't think about it.
    On the spectrum of being an optimistic or pessimistic person, I'm a realist. I can tell you that sh*t happens and then you die; that includes good and bad things. So keep your chin up, keep being yourself, and have fun as much as you can. :) One day, we'll meet someone out of the blue and this will all be a funny story

    1. Agreed. A huge part of the issue I think is that a lot of people our age are in transition in their lives. They don't know what they want or are focusing their energy on a career or other achievement.

      TOTALLY agree on the same life goals. It's critical. I've also dated someone who did not have the same goals and standards for life that I had. It made me lose interest because I felt he never challenged himself and was just happily going along with his little rut in life.

    2. It's definitely difficult to be with someone who is unmotivated. If I hear anyone tell me that they just see everyone as people just trying to get by in life, totally a red flag. There's so many things to see and do and many ways to be a better person.

      I would never sacrifice my career/goals for another person, but I do know how to make time for other people. So I hate hearing the "I don't have time excuse." I can rant all day, but I'm sure I'm preaching to the choir. :)

  8. This is a really interesting post. It's a phenomenon that occurs for men, too. Myself, I'm a good looking guy, educated, ambitious, a 'nice guy'. What I find most interesting about dating in my late twenties is that singletons of this age seem to have a paradoxical attitude (myself included): we're interested in the people who don't show us interest, while we aren't interested in those who do. Is it a matter of pride? Of the girls I have dated, they either come off too desperate or too aloof. Both are traits I see in myself. I'm constantly asking myself, 'How do I overcome this?' 'Can I overcome this?'

    Anyway, know of any books on the topic?

    1. I think I'm the female version of u! Good God! Basing it on your comment only of course

  9. wow, great post, I read most of the comments then stopped after the anti-social guy lol

    i guess most of the posters here are females so ill chip in my 2 cents as a late 20s single guy:

    back in college, i found dating to be extremely difficult, talking to 'girls' was like getting prepared to be insulted constantly. i felt powerless against those girls (mind you i was good-looking and had a laid back personality). none the less, i never developed hatred towards women. the girls that i'm talking about are the ones that think the world revoles around them and so i had quite a difficult time dating (should i say i didn't date at all? lol) after college, i focused my frustration on my career which turned into a good thing.

    i bought a home and was earning a decent income. now that i'm 28, i feel that the tables have turned dramatically and women (80% of the time) will come swarming at me (looks + personality + home + humor = attraction, forget the PUA stuff ;) )

    right now, i'm starting to feel the power all early 20 something girls posses: brush this one off, brush that one off, and go for the better one, then brush that one off too hahah

    i still meet girls in there early 20s that are self centered but i just brush them off ha! because i have such a big pool to choose from.

    All in all, i think this is just a cycle of karma. i hope the author will find the right guy and thanks for a great read!

  10. I can only agree with the original post.. Im a 28 yr old girl in London, and I find it really difficult to meet new guys who i can share something meaningful with. Ive done pretty well career wise, and am quite attractive... Not having been dating for a while has lessened my confidence a bit now although i too had plenty of guys interested in me at university. I have the same thing as one of the other commenters, where Im not interested in the guys interested in me... which is just great! And online dating seems so... contrived. Thanks for sharing and good luck!

  11. I can only agree with the original post.. Im a 28 yr old girl in London, and I find it really difficult to meet new guys who i can share something meaningful with. Ive done pretty well career wise, and am quite attractive... Not having been dating for a while has lessened my confidence a bit now although i too had plenty of guys interested in me at university. I have the same thing as one of the other commenters, where Im not interested in the guys interested in me... which is just great! And online dating seems so... contrived. Thanks for sharing and good luck!

  12. I am reaching my mid 20s. I've never been in a relationship only a few dates that did not work out. I find it difficult to find someone. I constantly get asked why am I single, I always get looks of pity... they think its a choice.. its not my fault I haven't found the right guy.It drives me crazy everytime I get asked about my relationship status..

  13. I'm living this right now. I'm a 28 year old guy and a bit of a homebody. I have no idea how to meet people and didn't even start dating until AFTER college. So I feel a bit stunted in that respect. What makes it worse is I feel that at this stage in our lives we start losing the passions that defined us as teenagers and through our early 20s but new ones don't necessarily fill in making compatibility with other people that much harder. This is due to not even knowing what we like to do anymore. Good times...