Online Dating for the Unconventional Woman

One of the results of the Internet age is that for my generation, we have experienced dating both pre-dating apps and post-dating apps. We are among the few who are able to attest to watching that shift and comparing the differences. When I was first dating, boys would make me mix tapes (or later mix CDs if they were from the nicer side of the tracks), hand write me notes, have to talk to my dad when he called my house, and possess enough courage to ask me out on a date in-person. For me at that time, I would have given him printed photos of myself (as any narcissistic teenager would), try to pry information out of his sister to find out if he likes me, and fight my siblings for the phone line to talk to said-boy into wee hours of the night.

Fast forward to 2017. Now I can Google search my date before we even meet to find out what he does for a living, where he grew up, if we have any mutual friends, what his hobbies are and if he checks off my list of boxes before going on a date. I can get someone’s number from a dating app and have hours of conversations before even meeting face-to-face. Romance is practically dead. Next to no one picks me up at my house. Gifts are rare. I have had a few men make me meals, but that usually comes after my consistent hints of how much I like food. When we go out, I’m never really sure if the man will pay until I get to the end of the date. I have even had times where his card was declined and I ended up paying for the date. There are no such things as grand romantic gestures. (Ok, there are a few, but they are nearly extinct). Then again, there aren’t those traditional games. You pretty much know what you’re getting within the first 20 minutes of a date. Red flags are more apparent. It’s a far more efficient way to date rather than the rigmarole of courting someone.

I’ve been dating in the Internet age for over three  years now and the number of guys that I have gone out on a date with from “real life” vs “online dating” is about 1/20. I spend most of my time swiping past people who I would never dream of going on a date with, then the majority of the rest of the time chatting/texting with the handful of ones that seem interesting enough, trying to figure out if this guy is really worth my time for a date. With the final fraction of my time, I MIGHT go on a date with the guy, but even if I do, it is not likely to end up in a second date.

I’ve gone on a LOT of dates in the past few years. Think about the math for a second. Let’s say I swipe left past 100 guys for every 1 that I talk to. Then I go on a date with maybe 1 out of 5 of the ones who I chat/text. The number of those dates that turn into a second date is probably half. Out of those, the men that I’ve “dated” for more than a few dates is probably around 10. And of those, I’ve only have one turn into a relationship longer than a month. Seems like a lot of freaking work for very little ROI. But I comfort myself by viewing it as a numbers game. I have to go on x amount of dates to find someone I’m interested in, so just keep going on dates.

Keep in mind, those numbers are all based on a dating app like Tinder where you have to match with someone in oder for them to be allowed to message you. Don’t get me started on the ones where just anyone can message you. You know in the spring time when you see a flock of about 45 male ducks all going after just one poor female duck who is hurriedly trying to swim away in the opposite direction? You feel so bad for her, but it’s like a train wreck and you can’t look away. Multiply that by about 15 and you’ve got Ok Cupid.

Don’t get me wrong. This is not a post about how terrible it is to be single and how everyone should feel bad for me. In fact, I really love my life. When I look around me, there are less than a handful of long-term committed relationships that I admire for their richness and compatibility. For the most part, I see broken relationships where neither one of the people is happy and certainly aren’t bringing the best out in each other. I don’t want a mediocre relationship, so I will gladly wait for the person who will bring out the best in me, be compatible to all of my weaknesses and flaws and enjoy and rich and fulfilling life together.

For the same reason, I don’t view the past relationships that ended as failures either. By the time I got divorced, it had been nearly ten years since I had dated, so I had a long learning curve ahead of me. I’ve been slowly figuring out what I want in a partner and frankly, what I want out of life. I am still discovering who I am, where I want to be and what I want to do, so to think about how another person would fit into that, shouldn’t be a rushed process. A relationship is a bonus. I have made huge sacrifices to build a life that I want and am proud out, and I can truly say that I am living out my dream. I am truly grateful for all of the experiences I’ve been gifted, so adding someone who would enjoy that beauty with me would really just be gravy.

Sorry, got distracted there for a minute. So what else makes online dating different than traditional dating? Well, I’m sure you’ve heard that online dating profiles can be deceptive. That is 100% true. I never really believe anything I read in someone’s online profile until it’s proven in real life. For example, men LOVE to talk about how much they enjoy adventure, camping, hiking, traveling, working out and being outdoors in their profiles. I guess it makes them sound more like a badass. Or something. So often times my first question to him will be, “what was your last great adventure?” I promise you I am not exaggerating when I say that 90% of the time the guy will answer something like, “well, I went on a camping trip with some buddies like five years ago…”

…. [insert annoyed emoji here]….

The other thing that happens with online dating is that you might see the person out in real life before your date. Especially if you live in a smallish city. Or even better, you’ll mention to one of your friends, she asks to see a picture and responds, “Oh yeah. We went out once. Super clingy. Watch out for that.”

Again…. [insert annoyed emoji here]….

This next one definitely crosses the line for me. Since I have an unusual first name, it’s not that difficult to find me on Facebook or through a Google search, so far more often than I would like, men will message me on Facebook or Instagram and say something like, “I saw you on Tinder and accidentally swiped left, but luckily I found you on Facebook! Wanna grab a drink sometime?” No. I can guarantee you that he did not “accidentally swipe left,” I was the one who swiped left and this was his desperate attempt to try to get my attention. Nope. Just nope.

So going back to how it’s pretty common for me and my friends to match similar people on online dating apps. Well, fellas, I hate to break it to you, but girls talk. Remember the guy from a few blog posts ago who told me that I looked like Alyssa Milano, but she is way hotter? Well, same dude happened to match one of my friends on another online dating site. She recognized him because I had shown her his pictures and told her the whole story of how rude he was to me during the entire date. So naturally, as any decent human would, I suggested that we start messing with him. So she started telling him about how she is so sick of rude men can be on dates by insulting a woman’s appearance and scarf and oh, she hates it when men don’t like travel… basically our entire date verbatim. Long story short, I think he learned his lesson in crossing the line from sarcasm into insults when on a date.

The most awkward part of online dating is when you see someone you thought your friend was dating on a dating app. Questions start rolling through your head such as, “Did they just have a fight and this was his way of getting back at her?” “Are they in an open relationship?” “Is he cheating on her?” “Does she know he’s on this app?” “Doesn’t he realize that someone is going to see this and tell her?” Remember how I said that girls talk? Well, that’s still true in this paragraph, just like it was in the other one. How could I not tell a friend if I saw her partner on a dating app? Girls gotta have each other’s backs, y’all. So inevitably I disclose the info and they guy is always on the defensive. Come on guys. You seriously thought that you could get away with that?

One of the best questions that I get from people I meet online is “You’re so pretty, why are you single?” Oh, the infamous question. If I had a dollar for every time someone said that to me, I would be living happily on my own private island in the Gulf of Mexico.

[Steps onto soap box]

This could be news to some of you, so you might want to sit down for this one. Not being single doesn’t mean “I’ve won.” Being single isn’t punishment or purgatory until you get to the “heaven” of a relationship. In fact, last time I checked, relationships are really hard. It’s hard to get to know someone, it’s hard to be vulnerable and open, it’s hard to figure out how to communicate with your partner, i it’s hard to trust someone fully, it’s hard to share your life and learn how to coexist together, it’s hard to adapt to each other’s eating habits. And you do all of that work knowing that on any given day, that person could break your heart. Not that those things aren’t worth it for the right relationship, but let me reassure you that being single really is pretty easy. No one tells me when to wake up or go to bed, I can eat whatever shameful meal of peanut butter/oats/almonds/honey mixed up into one giant glob and call it a meal, I can sit in complete silence for hours and not be disturbed, I don’t have to go to anyone else’s company outings or family dinners, I don’t get in fights, no one is around to eat the leftovers I was saving, I can change my plans last minute and no one else will be affected or annoyed, all of my disposable income is truly my own, and the list goes on.

I’m not trying to bash relationships. My point is that being single can also be pretty great, so please, let’s stop shaming those who aren’t married by wondering how could it possibly be that no one loves them, or wondering what’s wrong with them, or encouraging them that, “don’t worry, you’ll find someone.”

Maybe when someone says they are single we should start by high-fiving them. And then ask them about the rest of their fucking awesome life.

Ok, off of my pedestal (for now, at least). At the end of the day, I view online dating as a great source of entertainment. I would much rather open up an app and hear someone else’s funny life stories than turn on a TV show. I would gladly spend an hour at dinner listening to what brings another human joy in life. I have made several dear friends through online dating apps and I am grateful for those people in my life. As for my faith in online dating’s ability to produce a life-long partner? Jury is still out on that one. Maybe I was just born in the wrong era?

Dating Advice for Women

A few months ago, I wrote a blog post about dating tips for men, so I thought it would only be fair to write a follow up post of advice for women. Some of this advice is based on my own personal experience and some is based on things I have heard from my male friends. Enjoy.

#1. Don’t Talk Politics on the First Date

I typically don’t like to talk about controversial topics until at least the 3rd or 4th date when I’m sure that I really like someone. Well, I broke that rule once. I went out on a date with this guy who I knew was trouble even before we met. There was just something about him where I knew that we wouldn’t get along, but he was attractive and liked outdoorsy things, so I thought, why not give it a shot. Is nothing else, it could be a good story, right? Well, it was.

We met for tea because he didn’t drink alcohol and we made small talk about our hobbies and swapped stories about our dogs. He told me about his Snapchat account where he gives little fun facts about history every day and has a pretty big following. I like when someone has a passion project, so that was a plus. I honestly am not sure what happened from there, but before I knew it, everything went downhill. He made some passing comment about how we need more money to invest into our military and I stopped him dead in his tracks. “Pardon me? More money for our military? The organization that we spend trillions of dollars on? Do you know what would happen if we even took a fraction of that money and invested into something like our school system?”

After that, he tried to be polite for about another 15 minutes of the conversation. Then all hell broke loose. We went back and forth about the role of government and how money should be spent. He kept arguing for bigger military so that we can patrol the world, because apparently someone has to do it, he thought it should be the U.S. — at the expense of the quality of life of our children and thus our future as a nation. Then finally at some point I made the statement, “Well, maybe we should just raise taxes. We have the lowest taxes of any developed country, so it’s about time we caught up with the rest of the world, right? Then we’ll have enough money for everything.”

He looked me straight in the face and had an expression like I just killed his dog. He literally got up from his chair and walked out of the cafe.

I think that means I won, right?

#2. Initiate the First Kiss

Listen up, ladies. It’s a sign of a confident woman when you initiate the first kiss. And any time I’ve done this, I’m always met with surprise and delight. I think I can safely say that as women, we know when the date is going well. We’ve got some pretty solid intuition in our brains, so when you know he’s into you and you’re into him — keep him on his toes, do the unexpected.

#3. Give Him Grace

I’ve had more than one man tell me that I should try to give every date a second date, no matter what. The rationale is that men get nervous and often times aren’t really themselves on the first date. Although I don’t always follow that policy, I do like the sentiment of giving the man some grace every now and again. Especially as we get older, I think women can start to formulate this long list of deal breakers and may be ruling out some pretty great guys. Especially when you are first getting to know someone, give the poor man some slack.

For example, he might not always say the right things. I’ve been told that my teeth are crooked, the hair too short or too long, my legs are “thick” or that I’m fat, that I’m too crass for a woman, or too abrasive, or how I’ve ranked in attractiveness compared to other women he’s dated… the list goes on and for completely inappropriate comments that I’ve gotten from men. As much as it doesn’t feel good to be told something like that (and this is not an excuse for men to keep doing it), but I try to give them the benefit of the doubt that they aren’t trying to be malicious. So I guess this point is advice for both women and men – ladies, try to be patient and recognize that he might mess up sometimes and men – lay off the insults. Yes, they are insults and just don’t do it.

#4. Don’t Make the Date an Interview

I’ve heard this time and time again from both male friends and men I have been on dates with: don’t sit down on the first date and just start interviewing the poor man. I know that your time is limited and you probably don’t want to bullshit around. But you’re talking to a human, not an applicant. Even if he’s not your future partner, treat him with a little bit of respect. No matter what his interests are or baggage or job status, I bet that if you just decided to listen like you would listen to any of your close friends, you’ll learn something.

I used to get really nervous when I would go on first dates because I worried that I wouldn’t like him or he wouldn’t like me. Or what if it was awkward, what if I just wanted to leave. But the thing that I would always say to myself is that, everyone has an interesting story. And every person is different than me and could have something to share that I might learn from. So even if we don’t have a lot in common, chances are that if I just view him as another person and not as a potential partner, I will enjoy hearing about whatever experiences he has had.

#5. Be Spontaneous

Men have a tough job – they have to come up with ways to impress you without even really knowing you. Men are usually the ones to plan the first few dates and the woman gets to decide if he’s worth her time. So if something pops up out of the blue that would be super fun to do with that person — take the chance and do it!

One of my (few) actual relationships was with a guy who had been planning a month long trip to southeast Asia, which happens to be one of my favorite places on earth. We hadn’t been dating that long and I knew that I wouldn’t be able to take off much time from work, but I figured, when will be the next time that I am going to have an opportunity to travel with someone else to southeast Asia? It’s hard enough as it is to find people to travel with, let alone across the world with, so I jumped on the opportunity. Within a few weeks, I had a plane ticket to Indonesia and swung my work schedule so that most of my time away was over Christmas and News Years and was able to take just a few days off of work. And let me tell you, it was the trip of a lifetime. I had no idea how beautiful that country is and was blown away at every turn. And since he planned everything, every new adventure was a grand surprise (I love surprises). It was definitely a stretch financially and I had to sacrifice being with my family over the holidays, but truly the adventure of a life time and something that I will never ever forget.

So go ahead, say yes to that crazy adventure. You won’t regret it.

#6. Challenge Him to Try New Things

One of my biggest complaints about men is when they have nothing that they are passionate about. If I ask you what you do with your free time and your response is, “I don’t know, I watch Netflix and sports,” I can guarantee you that you will need to move along. Or worse, if you list off a bunch of hobbies that you did five years ago and it I later find out that all you do is Netflix and sports… you’ll have hell to pay.

There’s little that is more attractive than when a man gets super geeked out over something and pours his heart and soul into it. I’ll speak for myself, but I think a lot of women can relate to the idea that yes, we want to be adored, but we also don’t want to be the center of your universe. Something besides your woman should make you light up in life.

I’ve heard from a lot of men that the same goes for women; sometimes women are just boring. So in order to curb that potential danger, challenge your man to do something new. It doesn’t have to be something crazy like traveling to a different country, but surely you have parts of your life that he hasn’t experienced that you can share with him. Take him to an art museum. Or make him a traditional family meal that you grew up on. Or find a secret spot for a perfect little picnic. Or find the most beautiful location in the city to watch a sunset.

#7. Say Thank You

Even though I believe men and women are equal, I do still like good old fashioned chivalry. But this is a two-sided coin, ladies. When he picks up the tab, say thank you. When he opens the door, say thank you. When he offers to pick you up, before accusing him of being creepy, just take it as a kind gesture (even if you don’t end up taking him up on it). If you’re going to expect to be treated in old fashioned ways, then you better respond with old fashioned politeness. I think as women we sometimes believe we deserve or are owed something from men. Don’t be a pretentious diva. If you want him to be a gentleman, then be a lady.

Dating Advice for Men


I’ve been back in the dating marketing for several years now and let me tell you, it is a jungle out there. I’ve gone out with men who are everything from financial advisors to scientists to private investigators to chefs to engineers, you name it. I have found that people are often entertained by the wild stories that I share, so I thought, why not write about it. For your reading pleasure, may I present to you the first of many blogs on my dating life:

6 Dating Tips for Men

#1 Don’t Go to Jail on Your First Date

I was a newly single woman in her late 20s and I had decided to download Tinder. It was a welcomed distraction as I was still healing from my divorce and like many people who have just come out of a long relationship, I wanted to prove to myself that I still “got it.” So I started talking to a few guys and one of them seemed really interested in me and we had a lot in common, so we finally decided to meet for drinks. This was so early on and I had no idea what the dating etiquette was anymore, so I was nervous to say the least. We were going to meet on Wednesday after work, so around noon that day I texted him to see if we were still on. I heard nothing. 4pm rolled around and I texted again. Silence.

Why would you pretend to be into someone just to blow them off at the last minute? And he didn’t even have the balls to cancel? If he didn’t want to meet up, he should have just told me instead of choosing the passive aggressive approach of not even texting back. So childish. This is why I hate dating, I hate these games, why can’t people just be honest.

Wednesday came and went and I still heard nothing.

But then… one week later, I got a text. He started off my telling me that he thought about lying, but wanted to be honest with me in hopes of mending some of the mess. He said that he was sorry he stood me up last week, but…you guess it.

I got stood up on the first date because the man was in jail.

He told me some jumbled confusing story about how he had all these outstanding tickets and got pulled over and went to jail, yada yada… but the best part was that after the long text chain of explanations, he asked if we could still go out sometime.

No, sweetheart. We won’t be going out.

#2 Don’t Say Anything Negative about Her Appearance

This seems like a no brainer, right? I mean, come on. Everyone knows that the last thing a girl wants to hear is something bad about the way she looks. Even if you are joking, just don’t do it.

I was on a second date. The first one had gone well. He had taken me to brunch at Three Sisters Café, which is one of my favorite spots. Now we were at Iozzo’s, a romantic little Italian restaurant just south of downtown in Indy. He was doing well so far – cracking jokes, asking good questions, listening. He had beautiful icy blue eyes. I found out that he was really into film so we were talking about actors and actresses and I happened to mention that sometimes people said that I looked like Alyssa Milano. He was quick to respond, “Ohhhhh… well… yeah, but she is way hotter.”

It gets better.

So then he continues into a monologue about his past girlfriends and how I rank in appearance against all of them. Supposedly the last girl he dated was not as hot as I was. She was also a brunette. But the girl who he dated in Florida, who was a Disney princess at Disney World and was blonde – she was definitely hotter than me. “Now that I think of it, she’s probably the only person I’ve dated who is hotter than you. But you’re definitely the hottest girl I’ve seen on Tinder.”

Face palm.

There was no third date.

#3 Don’t Steal Someone Else’s Identity

There are certain people who ask me out where there’s something in my gut telling me not to go on a dinner date with them. I realize now that this is a sign that I should not go on any date with them, but at the time, I thought that this gut check just meant I should grab drinks and scope him out before committing to a full meal.

So I went out with this man, we sit down, order our drinks and start talking. The first pause in the conversation he says to me, “Some people are intimidated by my size. I mean… I’m so big and tall. I hope that doesn’t bother you.”


I ignored the comment and change the topic of conversation by asking what he did for a living. He told me that he is a financial advisor and is making six figures working for himself and also travels all over the country doing so. He doesn’t usually stay in one place for very long, so this may be the only time we get to hang out.

Oh brother.

I end the date prematurely and texted a mutual friend to give her an update on how it went. He’s kinda creepy right? Yeah, a little bit more than kinda creepy. Three weeks later this mutual friend texts me and says, “Hey, so remember that guy you went out with? Yeah so… he went to jail for identity theft. I knew something was off about him. Guess you dodged a bullet on that one.”


#4 Do Share Your Horrible Date Stories

There’s nothing that lightens the mood better than swapping terrible date stories with your new fling. That’s a sure way to make me laugh and it’s a fantastic ice breaker. It’s also a way to remember that everyone else is also trying to navigate this crazy thing we called love.

One of the guys that I went out with told me a story of his very first date after his divorce. Understandably, he was nervous about the date, just getting out there for the first time in a long time, but they had been texting a while and he was interested in her. They sit down at dinner, enjoy some small talk, then… out of the blue… she says, “hey, so I’m pregnant.”

The guy puts down his fork. Pauses. Leans in. Looks her in the eye and asks… “Is it mine?”

At this point in the story I’m pretty sure I snotted beer out of my nose because I was laughing so hard. I guess she didn’t think it was as funny as I did.

#5 Do Bring Her a Present

I know I’m speaking for more than just myself when I say that women like presents. It might feel old fashioned or seem like you are trying too hard, but I am telling you – the odds are in your favor. If you bring a present and she is mad about it, I’ll reimburse you.

One of the best presents that I received on a first date was flowers. Not fully bloomed flowers, but flower seeds to plant in my tiny garden boxes on my deck. It was spring and such a thoughtful present. Despite my lack of a green thumb, I love plants and flowers and greenery. Extra points for creativity. It came with this note:

Image 1

I LOVE notes. I find them so enchanting and like they are little piece of your heart that you are sharing with the other person. It is created with your words, original thoughts, and meant to be just for one person. If that doesn’t make a girl feel special, I am not sure what does.

#6 Don’t Fall Apart If Things Don’t Work Out After the First Date

Le sigh… I’m just going to put this out there. If you are in love with someone after the first date, there’s probably something wrong with you. I’m sorry to burst all of the “love at first sight” bubbles, but movies aren’t real life.

We were at a restaurant sitting in a booth. I started to be concerned when he asked if he could sit on the same side of the booth as me. Warning bells went off. He was a nice guy, but a little too handsy and a little too much talk about when he can come over to my place to “see my artwork.” There just wasn’t any chemistry and it ddin’t feel right. So we texted a bit the next day and I explained to him that I didn’t think it was going to work out.


He told me that I wasn’t being fair, that I hadn’t even given him a chance. How could I do this to him? Can’t we meet just one more time? Talk to me. Tell me what you’re thinking. Stop ignoring my texts. This can work. We’re a great match. What do you need me to do? I’ll do anything! Lara. Lara. Lara. LARA. LARAAAAAAAAA.

Oh boy.

That’s not romance, fellas. That’s just bat shit crazy.