On Dating

Whenever I’ve asked what you guys want to see more of, I get questions about my dating life. i usually completely deflect the question. It’s not something I’ve ever really wanted to talk about publicly.

Too many people read this blog! Coworkers, brands I work with, real-life friends, Internet friends, random people I went to high school with, and lord knows who else. I still maintain that I probably will never blog about the man I’m dating until I’m sure he’s the one, because I don’t want this blog to become a record of my romantic misadventures. 

But, hey, I haven’t written a post that makes my heart race a little bit when I hit publish, so let’s go for this.

Last night, I went out for St. Patrick’s Day. I went to a party at Junior League, got into a cab to come home, and decided that I’d actually go meet some more Junior League friends at an Irish bar they were at.

IMG 5865

I mean, my nails were green, and I was wearing a cute green dress. I couldn’t just go home. I had to do my Irish relatives proud, right?

When I was overweight, I really hated dating. I didn’t think there was any way anyone would ever date me. I tried halfheartedly, but I really hid behind my weight. I didn’t let anyone get close, because I thought once he realized I was overweight, he’d leave me. You know, because he couldn’t tell right off the bat?

I’m fairly outgoing with girlfriends, and with guys I’m not interested in, but I am absolutely, totally and painfully shy with any man I might be potentially interested in, because I’m terrified of being hurt.

When I lost weight, I did think it would change my dating life. That it would give me worlds of confidence I never had before. It very briefly did, but as I got used to my new body, that confidence retreated right back to where it came from. 

I’ve had a whole bunch of conversations lately with different women in my life about dating. One of my friends said she loves going up to guys in bars, and that’s how she met her current boyfriend. “But aren’t you afraid of rejection?” I asked. She said that nine out of ten times, she got rejected, but she knew she had to take chances.

Since losing weight, I’ve tried to date but after putting myself out there and being rejected (or, you know, meeting total trolls), I’ve retreated back into my life of being single and fulfilled, but still wanting someone to share my life with.

I found a great article this morning a friend wrote about “missing being fat,” and so much of the dating stuff resonated with me, but I love how at the end she talked about easing herself into her body confidence.

I told some friends who don’t live here recently I was going to make myself date more this year. They asked how dating in NYC was. “It kind of sucks,” I told them, “but I can’t imagine leaving here right now, so I have to believe there’s someone out there in this big city for me.”

So, out I went last night, and (okay fine, maybe fueled by some Guinness) I danced like nobody was watching, rather than shyly and self-consciously. And what do you know? Two different guys came up to me to dance. I didn’t think about what it meant, or whether they liked me or not, or if they’d ever want to see me again (or vice versa.) I let that guard down and let these guys twirl me around.

And I had a lot of fun in that cheesy Irish pub.

Here’s to more of that.

No, but really. Give me your best dating tips/tell me how you met your significant other.

44 comments on “On Dating

  1. Ashley

    Lady you are a CATCH and we all know it. You find the right guy and he is going to wrap is up, no question. So enjoy meeting lots of new people, the right one’s out there (maybe an Irish dancer!)

  2. Britt

    I live in NYC so I feel your pain of the dating process. I work long hours, followed by the gym, on top of a million other things I would rather do (or friends I’d rather hangout with) than participating in awkward dating interactions. The best thing I’ve found that works; meeting friends of friends by accepting social plans with acquaintances on the fringe of my normal group and oddly, trivia night at bars with random teams (asking a few people to
    bring friends). It’s an exhausting process no matter how you look at it but at least some of us are in it together.

      1. Britt

        @Theodora Blanchfield: See it takes me days to reply to a blog comment. A date prospect would just be plain hopeless! But for real if you want to do trivia, I’m down. Ya know, with a group, or it defeats the secret matchmaking purpose. I live in Midtown West and work in Meatpacking so I think we are probably in the same areas. Soulmate Hunt 2014. Or drinking through 2014. Same diff.

  3. Katie @ Live Half Full

    I met my husband at one of the divey-ist bars in Chicago, but I think it had more to do with the fact that I was in a really good place with myself at the time. Just keep putting yourself out there and eventually you’ll find someone who makes you want to date!

      1. Katie @ Live Half Full

        @Theodora Blanchfield: Definitely! And, it probably sounds like the most annoying advice ever because EVERYONE tells you this when you’re single, but I really wasn’t looking. I was just doing what made me happy in life and working on my career, getting in shape and making friends when it happened. So just keep living your life and working towards your amazing career and fitness goals!!!

  4. Shannon

    I LOVE this post! I met my current bf when we were randomly assigned to be partners in a group project in college, 6 years ago. We started dating a few months later. I think my three biggest tips are 1. Be you, because you are awesome; 2. Be confident, believe you are awesome; 3. Sometimes it pays to be bold. Also, I think texting and the college hookup scene made dudes of our generation bad at dating and communicating. But don’t let the duds get you discouraged.

  5. Lauren

    Great post! And these comments are so spot on, love yourself first and love will following. Carrie Bradshaw obviously said it best: “the most exciting, challenging and significant relationship of all is the one you have with yourself. And if you can find someone to love the you you love, well, that’s just fabulous.”

  6. Lori

    I might my boyfriend when I joined a kickball league! It’s a great way to meet new people in a laid back setting. A lot of our friends met at kickball as well. Look for a trivia league, or dodgeball or kickball, or bocce. Good luck!

  7. Valerie

    If you want to meet a guy, go where the guys hang out! For example, the weight room at the fitness club is an ideal place. Men will help you rack weights, show you how to deadlift, and admire your muscles (as well as other body parts). Believe it or not, intelligent men do lift weights!

  8. Becky @ Olives n Wine

    Good for you for getting out there and just dancing! I’m exactly like you when it comes to being outgoing with friends and then embarrassingly shy around men… Granted, I’m married now so it doesn’t matter anymore. I feel like once you give up on trying to “find” someone, they find you. I was happy being single and living life when my husband found me. Strange how that works…

  9. Isabel

    I met my husband through mutual friends (meeting up for a group dinner/going clubbing and running into friends of friends etc). I was/am nowhere near as socially active as you so this may work for you! My husband happened to be out with his friends and one of my friends was friends w him and his friends (helps to have friends with lots of guy friends I guess) . Anyway, we talked briefly but I didn’t think anything of it. It seemed like after we met I kept running into him..now he admits he tried to go to any group event I would be at:) so keep your eyes open- you never know who you might meet!

  10. Katie @ Talk Less, Say More

    Oh man…I’m totally not the girl to go to for dating advice…hollllaaaa to your fellow single gal! 😉 But I’m pretty sure dating sucks everywhere. I’m in the suburbs of Chicago and I swear everyone is either in a relationship or married, or if they are single, they’re a total troll. But I think sometimes it’s about just relaxing and opening ourselves up as you never know who that person who catches your attention might be. I’ve ISH started seeing someone in the last couple weeks…he’s not who I would picture myself with and he’s 10 years older than me, something I also would have totally blown off. But at least for right now, it’s worth pursuing and seeing what comes of it, letting my guard down a bit and enjoy living in this moment. (well that was a novel…sorry about that) 😉

  11. Jane

    Online dating! That’s how I met my boyfriend of over a year online. One would think it would be easy to meet men in the city but it’s kinda hard.

    1. Beckett @ Birchwood Pie

      @Jane: I agree with Jane. Online is the way to go, especially since there are more men online than women. OK Cupid did wonders for my love life. I only regret that I waited so long to try it. And I agree about not blogging about your dating life. It puts too much pressure on the relationship.

  12. Shawna

    love the part about dancing like nobody is watching and gaining back your confidence in yourself, regardless of whether there are guys around or not. that’s where it all starts — you being so happy with YOU, and then the right guy(s) will see what’s so wonderful about you and be attracted to it, too. i love love love dating and haven’t been much of a serious relationship girl, esp in NYC — i think the best advice i can give is to be as confident as you can in yourself, be open to talking to people (a conversation doesn’t mean a commitment), smile a lot, be honest and interesting, and don’t be afraid to flirt a little (if he’s cute!). so what if he doesn’t ask you out? some will, some won’t. and that’s okay. i know it’s cheesey, but that whole “be the kind of person whom you’d want to meet” shpiel is true — think of what would attract you to some guy you meet at first impression, and then think of what you’d want them to see in you, if they only have one chance. and not taking yourself too seriously always helps. i like to laugh at myself. a lot. 🙂

  13. Katie

    Yay! I had a similar experience last year for St. Patricks day, a redhead named Patrick actually gave me a kiss on the cheek (i thought it was adorable, but didn’t blog about it because I also don’t share dating stuff). I totally understand your not wanting to share. I did a 6 month subscription of match and when i didn’t find “the one” (I wasn’t suprised by this) I now have 6 months free. I’ve gone a few dates, but I only respond to emails and only to men I am interested in. I don’t get as bummed out when I play by these rules, I know that if they aren’t emailing me, its not meant to be.

  14. Jessica R

    My husband and I met online. I liked online dating because you could weed out the losers without wasting a whole lot of time. You also do have to go on a bunch of dud dates but I actually found it kind of fun. I am all for internet dating!

  15. Megan @ Meganmumbles

    I totally get the whole dating in NYC thing.. Before I met Mat, my fiancé it was rough. I noticed most of the guys in New York are really full of themselves or shy. I even had some try to date me who had girlfriends! I eventually ended up doing the internet thing and I was really happy I did. It take a lot of time but it weeds our those who aren’t serious. It also helps you figure out what you really want in a boyfriend and hey it def helps with your self esteem.

    Great Post!

  16. Marc Pelerin

    I met my now-fiancée 3 years ago on St Patricks day weekend at a road race’s “after-party”. I had no intentions of meeting anyone and was just myself. You’ll find someone – hell, the city is big enough!!

  17. Carolyn

    Best dating tip: stop looking. I think that when you let yourself love your life as it is, you attract people who want to share that life with you. Be open to the universe and to the possibilities and new connections (whether they’re romantic, business, or just friendly). I didn’t date for years after a college boyfriend broke up with me, and I fell into a bad place for me (gained weight, got lazy, retreated into myself). I wondered if I’d ever meet anyone. I think maybe deep down I realized that if I didn’t think I was a catch (I just felt stalled in my life), why would anyone else…so I created the life I wanted, the person I wanted to be (the person I’d always been but hadn’t really been for years). I focused on getting my sh!t together—started running again, focused on making my career goals happen, started looking at every person I met as someone with a story, tried new things. I stopped freaking out about meeting someone and just lived my life. And then I met my husband through my new job. And thank goodness—I’m terrified what type of person would have been attracted to the lazy, desperate, self-loathing me…would I have ever been able to become someone other than that? Anyway, you already have your sh!t way more together than I ever did at that age! It’ll happen.

    1. Theodora

      @Carolyn: So, when I was younger, I was definitely more self-loathing/feeling sorry for myself, etc. I feel like I’ve focused really hard the past few years on creating the life I wanted, etc. Still waiting 🙂

  18. MOM

    Hello, I know I’m only your mother and noone wants to take advice from a mother
    but I have been around for awhile and things haven’t changed that much when it
    come to men and women through the ages. Or as your Nana always said
    “put the music on and keep on dancing” I guess she was right!
    So, if you need a little advice, Hello I’m here


  19. Ange @ Cowgirl Runs

    Well, how’s this for a first comment on your blog?! 🙂

    I was married for 7 years – I met my ex when I was 17, so I’ve never really dated. Now I’m 30 and I have no idea what to do. I’ve semi-thought about signing up for online dating but I can’t even pull the trigger on that one. I’m solidly in the “I’m an awkward introvert and maybe someone will find me” mindset. I know that’ll need to change eventually, but for now?! Yikes!

  20. Emily @onesouthernbelleonebigcity

    I wish I could give some really sage advice on this one, but alas I don’t know that I can. I am married and have been for about 9 months. I met my husband through his mother. Yes, his mother was our matchmaker. I knew her through work and she approached me asking if I was dating anyone. I wasn’t very interested in seriously dating anyone, but told her she could pass along my email address to her son. (Talk about non-committal!) So, a month and a half later he finally emails me, a month after that asks for my phone number, and a month after that I finally asked him out! We got married 13 months after our first date. Bonus here, I didn’t have to worry about impressing his parents since his mom obviously thought I had some redeeming quality for her son. 🙂

    The point is, like others have pointed out: be in a good place with yourself, be open to the suggestions of friends (or Mothers!), and take a chance. A first date can always be the last date or it can be the first date of a lifetime commitment. I’ve dated a lot of bad fish, but I’ve had the fortune of dating some really great ones even if only one of them turned out to be my husband.

  21. Kas

    When I was heavier I did not date at all. I got rejected all the time. I never thought it would happen and I tried being flirty and approaching guys. Fail. It happened when I least expected and at a hole in the wall bar down by Chambers St. So whoever said to “stop looking” – I concur. It will happen – just be positive – positive begets positive.

  22. Alice

    I wish I had a long and complicated and romantic story, like in HIMYM or something 🙂 but we met at work and it just kicked off 🙂

  23. Nina

    I met my husband at an IHOP. He was visiting from out of town. We were seated next to each other. We talked through breakfast and I gave him A bit of information about myself. I didn’t give him my name or number. But based on the info I had given him he was able to locate me online by contacting my previous employer. My former coworker recognize the description and knew it was me . Needless to say he made another trip to see me the next weekend. A 5 Hour Drive.

  24. Emily

    I love that your mom left you a comment on this post! (Totally something my own super awesome mommy would do too…. haha)

  25. Nicole

    Cute outfit!
    I like to think I have enough dating stories to some day write a NYT best-seller.
    I worked with my SO’s sister–for 2 years she kept saying I had to meet her brother. I was dating someone else and actually tried to set my best friend up with him.
    When we finally met up (his sister had been in the hospital and told him it was her ‘dying’ – not really – wish that he call me) we hit it off and have been together since.
    I got to a point where I was really only going to trust meeting someone via a friend.

  26. Rebecca

    I met my boyfriend of two years, indirectly, through OK Cupid… and meetup.com. A girl who lived near me sent me a message on the site and said she was starting a meetup group and asked me if I wanted to join. I checked out the meetup group – it was mostly a group that met for meals, hikes, and bowling, which sounded good, so I joined. This girl had also been sending out lots of messages to other people on OK Cupid recruiting them for the group. Anyway, at the second meetup I went to I met my boyfriend, who was one of the other people she had recruited. We started talking about travel and music and hit it off and he got my number. We met up a couple weeks later to go hiking (just as friends, wasn’t a date yet) and ended up spending the whole day together. And then a few days later we went out again, which I wasn’t sure was a date or not, but it was pretty clear by the end of the night it was a date. I tell him that we owe a lot to the girl who randomly recruited both of us from OK Cupid! I agree with others that you tend to meet someone when you’re not really looking or in a way you would never have imagined. Although I was on OK Cupid, I had just been through an annoying heartbreak and wasn’t really looking for anything serious. I also agree that you have to go through a lot of rejection to get anywhere – a LOT – so you just have to grit your teeth and bear it. But there is truly someone out there for everyone. So I hope you find your someone soon 🙂

  27. Lisa Jones

    Congrats on going out on St. Patty’s day. When I lost weight I looked great in the mirror but still had insecurities on the inside that prevented me from dating (especially stretch marks). The only thing that healed that was time and I am now married with 3 kids!

  28. Chrissy

    This post hit home. I was heavier in university and rarely dated. When I came home, I started eating right and took up running…sound familiar? However, the men still didn’t come. Looking back, I think I closed myself off and when I did meet someone, i would come on too strong. For many years, it killed me to be the last single girl of my group. But….I had a tranformative moment as a ran up a huge hill that “I was OK” and had to enjoy the life I was in and not the one I’d wished for. I did that for a few years but would continue to go on blind dates and keep my eyes open. Finally, a friend of a friend introduced me to my now husband via an email! We’ve talked about the fact that we both had to be in the right space for it to click. By the way, the wedding had lots of chevron and I tried for pink and green colours but my MoH steered me to grey & pink instead with no regrets!

    PS I always enjoy your mother’s comments. She’s always bang on!


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