Jamie Shupak is the Emmy-nominated traffic reporter for NY1, the Big Apple cable network that’s the end-all and be-all on all things Gotham for New Yorkers. She’s also a beautiful, single woman navigating New York’s treacherous (and hilarious!) dating scene. In her weekly column she shares her war stories and offers her advice and admonitions.

I am an eternal optimist, albeit very much a realist. I get that stuff happens and sometimes things just aren’t right in a relationship. What I don’t get is when people decide to take the easy way out rather than come clean about their feelings or actions. This was the situation with my ex-fiancé back in September, and I can tell you the reason he's not in my life anymore has much less to do with what he did, than how he handled the whole thing. It was simultaneously the ugliest thing anyone has ever done to me and also the biggest gift anyone has ever given me.

If you’ve ever had a broken heart you know the twisted ways in which it changes you. From what I can tell though, more often than not it’s how the relationship ends rather than why that leads to any hurt, animosity, or sadness. Knowing this, I made a promise to myself when I began dating again that I would always be 100% honest about my feelings and intentions and would never lead anyone on. Of course, I would also always do what was best for me. It’s not an easy balance. Likewise, ending it, saying goodbye, walking away, whether after 10 dates or 10 years, is never easy. But at least I can sleep at night knowing I handled (and sometimes ended) things with each guy gracefully.

YOU WANT THE TRUTH? YOU CAN’T HANDLE THE TRUTH

Actually, I can. I’m a big girl. Choosing between the truth now or later, I’ll take now. It hurts less if I hear it from you right now than if I find out later from someone else. It's such a slap in the face to be lied to, which is why I’m a straight shooter these days. I went out with this one guy a bunch of times who I really like and respect, but one night, over dinner, we got into a pretty serious conversation. He asked me how many other guys I was seeing, if I wanted a boyfriend, and where I stood on love and relationships. Though squeamish at times, I answered every question honestly. After he dropped me off I replayed the conversation over and over again, realizing that he was curious because he probably wanted more from me. It was time to live up to my promise and tell him I didn’t want more. Since we had spent a good amount of time together and made most of our plans over the phone, an email wouldn’t do. I had to call him.

I’ll admit it. I was nervous. I dreaded hurting his feelings. Luckily, this guy’s a master on the telephone so it wasn’t awkward or heartbreaking. After clearing the air, we found that we were both on the same page. And even after calling me a “sorority girl” and saying he "knew he wasn’t going to marry me," weeks (months?) later we continue to hang out. Though the truth can be brutal, it’s really the only way to go if you want to show class and respect, or have any hope of talking to that person again.

HEY, AT LEAST IT’S NOT A POST-IT

I called that guy for good reason. We had been out numerous times and we had always made plans on the phone; there was a legitimate something there. On the other hand, this other guy I went out with, though he was a really good dude—and an old friend of my family’s—I just wasn't feeling it. It didn’t help him that there was another guy in the picture who I was into, either.

Both times we went out it just felt like we were old friends. When he kept trying to make other plans, it was time to come clean. Here’s the pertinent part of the email:

Anyway I started seeing this guy about a month or so ago and it's starting to get a bit more serious, and I'm interested to see where it might go. Out of respect for him I don't feel right dating other guys... so can we hold off on next Wednesday? I just wanna give things with him the fair shot I think it deserves. It's really nothing against you, I hope you know that. I think you're awesome, really.

Bear in mind I checked with two close guy friends who know all my intimate dating details and they thought an email was perfectly appropriate. He didn’t agree.

i've been on both sides of this equation enough times to know that I was probably moved from the front stove to the back burner to simmer a bit. Disappointing, sure - but not unexpected or unprecedented. sometimes even when people might be good for each other, as i think you and i were/are/might be, timing really is everything when it comes to these kinds of things. the only objection i might have here (and not that i feel i'm owed anything from you after just 2 dates), is that next time (should there be one), this is really the kind of conversation you have over the phone instead of in an email - even if email has been our preferred mode of contact. Still - there is no ill will here and I'm genuinely happy for you. I'd tell you I hope things work out for you and this guy, but that'd really only be half true. In the coming weeks or months, should you come to the realization that this dude is not quite as awesome as i am (and really, how could he be?), you got my number and email and I'd love to hear from you - maybe next go around i'll be the dude that gets the fair shot. If not, not. still no hard feelings.

YOU DON’T REALLY LOVE ME, YOU JUST KEEP ME HANGIN ON

This isn’t just one of my favorite songs to run to—these are words to live by. Leading someone on is not nice. I’m very much a “you feel it or you don’t” kind of person, which is why I would never want to waste anyone’s time, much the same way I’d hate for a guy to keep seeing me because maybe—just maybe—he’ll decide he’s into me. I know on a first date if I’m into you and want to hang out again. The problem arises when I know I don’t. While some of my guy friends insist that after a first date you can just ignore a guy if you’re not interested, I think, especially if they contact you for second date plans, it’s classier to level with the guy. I actually sent a similar email to two different guys recently:

So I had a good time last week hanging out, I think you’re an awesome guy… I just don’t think you’re the right guy for me. And hanging out I feel like would only be leading you on, which to me is just uncool. I had fun, and respect you, which is why I just wanted to be straight up with you about how I'm feeling.

Here’s one guy’s response—pretty much what I expected:

I 100% understand, appreciate your candor - very refreshing. I've found myself often going on 2-3 extra dates just being "polite" which certainly doesnt serve anyone's benefit in the end.

Sometimes, they fight for it a little, which I respect. But resist the urge to respond—you’ll just dig yourself a deeper hole.

Hey Whats going on. I wouldn’t normally write back after knowing you weren’t interested but just thought I’d say hi. I had a great time hanging with you, and it would have been cool to get to know you better. I think you’re a pretty cool chick, and I think I’m a pretty cool guy… what else could you ask for ☺ You didn’t even see my fun side yet… I bet it was b/c I told you I was a mets fan.

If you’re interested in staying in touch write back sometime, you won’t be leading me on, and I totally respect that you told me instead of ignoring me. That says a lot about you. But it’s still nice to know and be friends with good people! I hope you’re doing well.

CAN WE STILL BE FRIENDS?

Get real. We all know the answer to this question.

TIMING IS EVERYTHING

Sometimes you’re lucky enough to meet someone special. Someone you click with, you see eye to eye with, someone who makes you laugh and understands where you’re coming from and where you’re trying to go. Sadly, sometimes that isn’t enough. I know because it’s happened to me.

I was set up with this guy and from the moment we started emailing back and forth, I knew there was something. He talked to me like he’d known me for years, and made me laugh in a way I’m not sure anyone ever has, or maybe ever will. We hung out almost every Friday night for a couple months and it was starting to feel a little more serious. I was telling all my friends and family about him, and for the first time since September I thought about what it would be like to be someone’s girlfriend. But I knew I wasn’t ready. It wasn’t about other guys as much as it was me not being ready to give the proper amount of time and energy to the relationship. I knew he wanted more and it was only a matter of time before the conversation we kept avoiding would be on the table in front of us.

So how to end this gracefully? Turns out, I didn’t have to—he did it first. One beautiful Monday afternoon we sat outside and talked for hours, until he walked me home and told me he couldn’t hang out with me any more unless I would be his girlfriend. As much as any other girl would have jumped at the chance—he’s a great guy—I had to be honest with myself. I told him I couldn’t do it. And for the first time since September, I cried over a guy.

In one of her famous breakup anthems, Adele sings, “Sometimes it lasts in love and sometimes it hurts instead.” This time it hurt. One day though, when I’m ready, it’ll last.

Next Week: Jamie answers your dating questions and solves your most difficult dating situations.

Also Watch

Close