Dating When You’re $120,000 In Debt

I thought my six-figure student-loan debt was making me undatable, but was it really the numbers that kept me from reaching the fourth date?

Here’s one from one of my female readers.

A lot hinges on the third date with a new person. By this point, you’ve seen enough of this potential significant other to determine the direction you want this newfound relationship to go in. A casual fling, your next serious partner, someone you’re sure you never want to see again—that’s all decided by date three. It’s the date on which you show your cards, air your dealbreakers, and hold your breath, waiting for the person on the other side of the table to respond.

So when you do have cards to show, you dread this date—which is how I felt sitting across from a man with whom I could envision a future, my mouth dry and my palms slick, trying to summon the power to reveal what I thought made me incredibly undatable. It was the reason I believed I was still single after countless awkward encounters. But I could tell things were going to progress between us—I was already imagining what falling in love with this beautiful bearded man would be like—and I knew I had to give him a chance to bail. Gathering all my courage, I formed the words I hated saying out loud: “I have student debt.”

After four years at the University of New Haven, a private university I couldn’t afford, and two years earning a master’s degree in journalism from New York University, I was saddled with a $120,000 debt for a career that did not guarantee a hefty return on investment. Although I loved my chosen field, I knew there were less expensive paths I could have taken. On my worst days, I spent hours tossing and turning in bed, desperately wishing I could go back in time and persuade myself to go to a cheaper school. I wished I had understood the gravity of what I was getting myself into, but I am the first child in my family to go to college, and neither my parents nor I truly understood the enormity of the debt I would be shouldering.

I felt suffocated, like I was barely treading water in a storm. I had already cut back in every aspect of my life—living at home with my mom, bringing lunch to work every day, switching to water after only one drink on a night out with friends—and it was barely a life I wanted to live. I couldn’t fathom finding a partner to join me in this misery because, ultimately, who would want to marry that burden?

I started to equate my self-worth with my net worth—and I was in the red.

I always knew dating in New York City was going to be hard. I had never been confident—I was self-conscious about my hips, my laugh, the way I rambled when nervous—and I often thought of a first date as Judgment Day. The few minutes before coming face-to-face with a man I had swiped into existence were always the worst; my heart would beat in my throat as I imagined him sizing me up, mentally comparing me with the person he had imagined me to be.

Being both single and in debt conjures anxiety like none other. You’re already at your most vulnerable while playing the field. Now mix in the possibility of rejection based on your financial situation. I started to equate my self-worth with my net worth—and I was in the red. If you’re worth what’s in your bank account, then I wasn’t just worth nothing. I was less than nothing.

I began to think, Why bother? I felt even if someone liked me for who I was, my finances would send him running. Choosing me meant hitching yourself to my debt—and why do that when someone with fewer financial complications was only a few swipes away?

It didn’t help that those fears had been confirmed. When I casually mentioned to the law student with dark olive skin and bright eyes that I had taken out loans for school, he had all but done a spit take. His eyes went wide and his head jerked back, as though the thought of anyone but your parents paying for college was ludicrous. “For journalism?” he asked. “Good luck ever paying those off!” He laughed, then took a swig of his beer, and a hot wave of shame washed over me. There was no fourth date.

Then there was the tall bass player sleeping on a mattress on a floor in Brooklyn who, despite all better judgment, I was very into. He hadn’t finished school and politely nodded when I broached the subject. In the moment, I felt relieved, but a week later, as I obsessively checked my phone for new messages and racked my brain for reasons he had gone silent, I couldn’t come up with anything other than my debt.

Sometimes the topic would surface naturally in conversation, which makes sense considering roughly one in four Americans are paying off student loans, averaging $28,800 nationally, after graduating. This happened on my second date with a charming physicist. He mentioned how many of his classmates had six figures’ worth of debt. He felt bad for them, he said, but he couldn’t relate. His grandparents had footed his bill. I swallowed hard as my stomach sank to my feet. This time, I didn’t bother bringing up my story; I already knew how this would end. Before we parted ways, we made plans to see each other that weekend, but after two restless nights, I canceled the date, using a canned excuse. “I’m just really trying to focus on work right now,” I said. “It’s not you; I’m just not ready for a relationship.”

Choosing me meant hitching yourself to my debt—and why do that when someone with fewer financial complications was only a few swipes away?

So, in September 2017, with a montage of these memories playing on a loop in my mind, I placed both sweaty palms on the table in front of me, looked into the eyes of the man I hoped to call my boyfriend, and said, “I have student debt. A lot of it.” He blinked once, twice, waiting for me to continue. When I didn’t, he cocked his head. “And … ?” he asked. I blurted: “Like, so much that I’ll probably be paying it off until I’m in my 60s.” He looked at me for a while longer, then shrugged his shoulders. “That blows, but you’ll get through it. You’re a motivated person.” And that was that. It didn’t come up again because he didn’t care. He didn’t like me any less. He didn’t disappear. We kept seeing each other until eventually we decided to date exclusively. My debt wasn’t the dealbreaker I had set it up to be.

Although my debt does come up when we plan for the future, it doesn’t seem like a liability; rather, it’s a challenge we’ll face together when the time comes to make big financial decisions. Since my debt-to-income ratio is skewed, we’ve discussed the possibility of leaving my name off the mortgage if we decide to buy a house. Although my debt is mine alone to pay back, he’s made it clear that I don’t have to weather the mental stress of it by myself.

Months after I bared all, he pointed out that I had gotten worked up for no reason. And that’s when it hit me: Worrying that my debt was making me undatable was what was actually making me undatable—not the debt itself. It was a self-fulfilling prophecy that I was willing into existence by stressing about it. Looking back at each failed date, I see now that it’s a very strong possibility that I was letting my anxieties and the shame I felt when I thought of my debt color how I interpreted the way those men had reacted.

Unless I’m the recipient of some huge windfall, my debt is something I’ll have to hack away at slowly over time, not something that will change overnight. What I can change is the way I perceive it and how I let it affect the way I conduct my life. My net worth doesn’t define me; my actions, my personality, and the way I live my life do. Instead of being heavy baggage, the thing I let determine my dating life, it’s now just another part of who I am. Now, two years after that fated third date, I’ve stopped worrying about it so much. Instead, I focus that energy on the relationship I’m in with the man who sat across from me that night, the one who accepted me for who I was, debt and all.


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The 6 Biggest Mistakes Men Make When Contacting Women Online For The Very First Time

Do you desire success with online dating? Online dating can be easy and fun if you avoid these six mistakes that men most often make when dating online. Here are the six biggest mistakes men make online when contacting a woman for the very first time.

1.Not Reading A Woman’s Profile: Of all the mistakes guys make, this is one of the biggest. Guys will not read a woman’s profile, then proceed to email her anyway — even if they are not in her age range and don’t like any of the same things she likes. It’s amazing how many men will just look at a picture of a woman and send her an email, when that woman would be 100% not interested based on what she said she’s looking for in her profile. When you do that, you’re just wasting somebody’s time.

2.Being A Winker: If you actually read women’s profiles online, you would see that a lot of women request not receive winks or say flat out that they don’t respond to winks. Since a lot of men online are very lazy, though, they will go online and send out a hundred winks in a night hoping that one woman will respond. When you do that, do you know what that tells a woman right from the get-go? It tells her first that you didn’t read her profile, and second that you’re pretty desperate. Winkers are desperate. They don’t care who responds; they just want someone to respond.

3.Sending A Generic or “Cut ‘N Paste” Emails: Sending just a generic or “cut ‘n paste” email when you haven’t read a woman’s profile is one of the biggest turnoffs to women online. Guys will send an email to a hundred woman saying something like, “Hey, you and I are really a match. Read my profile and check it out, and let me know what you think. Looking forward to hearing from you.” When a woman reads this, she knows you have put no effort whatsoever into it. She knows it is a generic email, and she is not going to respond to it.

4.No Follow-Up: Lack of follow up is another huge mistake men make online. A man will send an email to a woman, she will send one back to him, and then he will wait and not respond to her email right away. He doesn’t follow up until three weeks later when he’ll email her and give some kind of excuse about being really busy at work. Do you know what a woman thinks when this happens? She thinks, “Well he obviously emailed ten people, and I was number four on his list. He was talking to three others, they blew him off, so no he’s decided he wants to go out with me.” You don’t make her feel important that way. If you email a woman, you had better follow through with it — both in terms of returning her emails and asking her out on a date. Women want men that act like men, have a plan and follow through it.

5.Commenting On Her Picture: Commenting on a woman’s picture shows her that you didn’t read her profile. If you write, “Boy, you look really great in that dress” or “Wow, you look hot in that bathing suit” it shows a woman that you are solely a visual guy. Doing it is too overtly sexual right from the get-go. It turns women off. Women want you to not only read their profile, but to comment on something she says in it. It shows them that something in their profile connects with you emotionally in some way.

6.Talking About Yourself In Your First Email: Talking about yourself in your first email (and first contact) with a woman and before you even ask her a question is a big mistake. It looks to a woman like you just cut and paste part of your profile into an email and sent it to her. What you are doing when you do this is being a “lister” — what I call men who have to list all their good qualities to sell themselves to a woman. What you should be doing in that first email is to flirt and get to know her better.

Online dating is a lot of fun, but you need to look at it differently. You need to look at your first contact with a woman as if you were meeting her live and in person.

If you look at it this way, you would never send a woman a list of all your good qualities or make a comment about how hot she looks in her swimsuit on the first conversation.

Think that way, and you may have greater success online and not turn any women off.



Rebecca – Chapter 13 – Airport – Part 1

“As I step from the train and begin to make my way towards the terminal, the old feelings creep back in like black serpents.”

I met Rebecca 3 years ago on a date. Rebecca has recently made an appearance in my life so I thought I’d re-run this series so everyone won’t have to go back and search for her series to catch up. Enjoy!

Fall of 2016

I solemnly rode the train to Philadelphia International Airport. Rebecca was leaving for South America to work as a nurse overseas to assist in a third world country.

This sucks. I’m having anxiety about all of this. I try to think about the airport as a place and not think about what is about to happen to me. To us.

To most, it’s missed connections and frantic jogs through security. It’s fast food and no outlets. But to me, an airport is one of the most romantic of places. Yes, I will admit, I have a love affair with airports. The romance of an airport is unlike any relationship I’ve had with other places.

The magical lights of the departure airline lists. The scrolling list of the television, filled with exotic locations – so many of which remain unexplored by my own two feet. “Departing,” “boarding,” “delayed.” Three words that bring a rush of energy coursing through my veins, each specialized and unique than the next. The sorted lines at security that empty out into the faraway destinations, some a skip away and others thousands of miles away.

I look to the woman ahead of me in line and I wonder, to where is she going? To the family of four, I ask, are they vacationing or leaving for a new life? And to the quiet, elderly man, I question, is he saying hello or goodbye? The romance of an airport is the diversity of the people that encompass it. The ethnicities, the religions, the ages, the families, the solo travelers, the young, the old, the excited and the anxious. All of which must go through the same lines as myself, and all of which await their adventures. The romance of an airport is that it is a microcosm of civilization. It is a glimpse of the greater world.

Each airport I’ve visited all share the same quality, they are a place of transition. No one stays, everyone leaves. Just like me. I will corner myself in a comfortable seat, next to the husband and wife double checking their seat assignments. I will put on my headphones and anticipate my upcoming adventure. But I, like everyone else, will depart.

But to see each person, in their vivid, bold realities – whether living through a nightmarish layover or seeing the glimmer in their eyes as they look forward to beginning a new chapter – it’s romantic.


The next time you enter the airport, remind yourself of these romantic notions. The romance of an airport is present when you look for it. Savor the (hopefully) short amount of time you have in a place as alluring, diverse and transitionary as this.

But as usual, I digress…

I’ve found that like my father, when I’m facing anxiety, I focus on something other than the current dilemma.

But as I step from the train and begin to make my way towards the terminal, the old feelings creep back in like black serpents.

I think about how before 9/11 one could walk all the way to the gate where the plane was boarding.

Now, you can get as far as the waiting area, and that’s it. No more can you embrace your friends and family and watch them walk through that little tunnel onto the awaiting jet.

The jet. That flying bus that takes your loved ones from you. That bad restaurant at 20,000 feet in the sky that serves tiny bags of pretzels and cups of soda.

I was always terrified of flying. Well, to be fair, I was always terrified of anything new and different my whole life. That’s the curse of having anxiety. But back in the early 2000’s I worked as a consultant and had to fly all over the country for work and became quite good at it all. It just goes to show, that if you have fear about something the best thing to do is to walk towards it over and over, and after awhile you’ll see it’s not so bad after all. Look at all of the idiots that fly all the time and nothing happens.

But today isn’t like those other times.

I text Rebecca.

She responds immediately.

She gives me her location and I approach. I see her across the busy waiting area. She’s sitting there with another girl who I assume is a nurse too. They’re chatting and looking at their phones.

Rebecca hasn’t seen me yet.

I pause.

I take a moment to think about who this woman is to me.

We met on a Tinder date. It was lovely. I see her and then I don’t see her. She drifts in and out of my life like the turning seasons. She’s so much younger than me. So what else is new? I always end up with these young beautiful women. It’s my curse. I fall in love with them and they with me. (Or, what I represent) But all of these stories end the same way. My own madness. They all grow out of me. They all move forward in their lives with what they perceive they should do and the learned choices they should make. They all eventually want to marry and have a family with a loving husband. I’m almost always that guy… but only almost. Almost honest. But never really.

I look upon her from a distance. She’s so beautiful. So alive. So full of hope and time.

Me on the other hand, I’m running out of time. I’ve had all of the love, relationships, sex, fun, laughs, break ups, and divorce. Who am I kidding? This could never work. This will never work. Rebecca will go the way of Alis, Michelle, Annabelle and probably Cherie. They all end the same. My madness drives me to make the same mistake over and over again.

But I’m addicted to the drug of love and romance. To me it’s better than sex. Romance is the best part of any relationship. At least for me. After that I lose interest. Like a lion after a kill. The hunt is everything.

Annabelle had cleared the cache for me to ever invest myself with anyone ever again. It all seemed a waste of time.

The tide rolls in full of life’s bounty, and then is ground into sand by the powerful waves of reality.

But with Cherie I was ready. I went into that relationship fully prepared with a safe exit strategy. I never did that before.

My father once told me that if I ever got into a relationship with a woman, I should always have a way to get out of it.

What an asshole.

But he was right. At least for me. I never believed his words, but I do now.

But Rebecca has a certain something that I find intriguing. There’s just something about this rare bird that’s simply different. She evokes a certain dark attraction unlike other women I’ve known. It’s not anything unusual… just different.

I’m old and experienced enough to know myself and my feelings. At my age, I know it’ll probably go down like the rest of my failed relationships. But in reality, I feel that in this moment, I may have lost an opportunity to do what I usually do and fail again.

Could the going of Rebecca be the thing that finally cures me from getting mixed up with all of these mixed up young girls?

She’ll get on a plane and leave the country and in a month or two forget all about me. She’ll be in a totally different place and time and I’ll be left back here in Philly. Just grinding away at what’s left of my life.

She’ll save me by leaving now instead of eventually leaving me later.

I’ve had all of the romance and courtship with her and now she’s decided to get away from me by leaving the country.

But that’s not entirely true. She’s young and has a wonderful opportunity to do some good in the world. I can’t make this about me. She’s not leaving me. She’s just going forward with her life. She has to do that. I did the same thing at her age. I went to California to play rock and roll.

I can’t stand here and agonize over this.

I have to go over to her and say goodbye.



Covid-19 Can’t Stop People From Looking for Love (or Hookups)

Sharing meals, hand-holding, and kissing can spread the coronavirus. That hasn’t stopped anyone from checking their dating apps.

It’s Friday the 13th!

Teens cough theatrically while their crushes spring away from them, retreating into their hoodies like turtles into their shells. Men and women walk up to each other on the street, stretch their arms out for hugs and their faces forward for kisses, only to jump back at the last moment and bump their feet together instead. A man walks down the street in a full hazmat suit, hand in hand with a coughing woman in shorts and a T-shirt while TikTok’s most ubiquitous new earworm—”It’s Corona Time”—honks and drones in the background. His caption: “When your girlfriend has coronavirus but you still love her.” Intimacy and social distancing do not mix.

As concerns about Covid-19 grow, many people’s minds have turned to romance. In China, where many have been on continuous quarantine lockdown for weeks, residents are sharing photos of stores emptied of condoms—hey, there’s not much else to do. In the United States, where would-be lovers are still free to leave their homes, citizens are more focused on whether dating during a pandemic is medically advisable. Stories about concerned and confused daters are everywhere, and people’s reactions to the outbreak range from seeking a hookup for the end of the world (and saying so in their dating app profiles) to instantly unmatching with people once they find out that their prospective mate has been on a plane recently.

Even the dating apps themselves have been swept up into the Covid-19 discussion. Tinder will interrupt your swiping to remind you that, while they want you to “continue to have fun,” you should also remember to carry hand sanitizer and maintain social distance. Queer-focused app Lex has also been reminding people to wash their hands and suggesting ways to keep busy and connected while quarantined. OkCupid has gone so far as to include a question about coronavirus—“Does coronavirus affect your dating life?”—as part of their users’ dating profiles. “We are always dropping in culturally, politically, and socially relevant questions for our daters to respond to,” says Michael Kaye, OkCupid’s global communications manager. “These questions help us match people on what matters to them.” Whether it’s desirable to be paired according to your infection anxiety level is up for debate, but OkCupid has found that coronavirus concerns definitely matter to people deciding whether or not to bring a new person into their lives or bedrooms.

The caution is appropriate. A typical date breaks just about all of the World Health Organization’s Covid-19 prevention rules. They’re public, and most restaurant tables aren’t 6 feet across. It’s likely you’ll touch hands, which is something people all over the world are trying to avoid. WHO officials have shared alternative greetings like waving, bumping elbows, and bowing. Then there’s kissing. The French government has officially warned its citizens against kissing each other on the cheeks, and Spain has instructed worshippers not to kiss statues of the Virgin Mary and Jesus, so you know this is serious business.

Considering coronavirus is carried in saliva and sputum, kissing is just about the most efficient way to transmit the disease imaginable, short of spitting directly into your date’s mouth. (We won’t yuck your yums, but maybe don’t do that until Covid-19 is under control.) “You could date someone new and make that connection high intensity, but you should then break many of your other normal contacts, especially those that end up reaching the elderly and infirm,” says Robert Glass, who has researched social disease transmission at Sandia National Laboratories, which investigates scientific solutions to national security threats. “Responsible individuals will choose to forgo dating entirely or shift it to online interaction instead.”

Illustrated woman, speech bubble, virus cell

Still, activity on dating apps is holding steady, and is actually expected to increase as more people quarantine themselves. The upswing in usage is typical of any event that keeps people holed up inside, and is sort of the digital equivalent of the Chinese run on condoms. People aren’t going to stop looking for love because of coronavirus—the strictures of coronavirus preparation have left them with little else to do. The apps obviously see this as a good thing: Some hope that their platforms will become a way for people to stay connected and meet new people without ever leaving their homes, especially if they (like Bumble) offer voice and video calls through the app. In some cases, preparations are also being made to field any questions users might have about Covid-19 safety and refer people to WHO and Centers for Disease Control and Prevention guidelines.

However, it seems that most people still aren’t averse to leaving their homes to find romance, despite anecdotes about spurned dates and paranoia hype to the contrary. According to OkCupid, 88 percent of people surveyed globally say they’re still dating during the outbreak. In the United States, the dating pool is still at 92 percent, though it varies by region. (The most nervous cities in America are Seattle and Miami, where only about 85 percent of respondents feel comfortable dating.) In countries that have been more seriously impacted by the virus, that number falls sharply. In South Korea, 71 percent of OkCupid users are still actively dating. In Italy, only 45 percent of people are willing to match and mingle at all.

As the outbreak goes on, daters in the US may change their minds and priorities, but for now the coronavirus seems more likely to inspire dance memes than genuine, celibacy-inducing panic. Even as people are encouraged to work from home and avoid large gatherings, and toilet paper, masks, and medicine fly off the shelves, people aren’t quite ready for their dating lives to go into quarantine. For most Americans, the threat of coronavirus still seems way further than 6 feet away.



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