10. San Diego, CA

SAN DIEGO, CALIFORNIA

Average duration of failed marriages: 18 years
Dating services: 7
Gallup Well-Being Index rank: 56
Gonorrhea cases per 100,000 people: 83.4

Being last on the list is actually a good thing, because it means that there are nine other cities that are more miserable than you, San Diego. With seven dating services in town, there are clearly plenty of people pining for romance again. And, with one of the highest rankings on the Well-Being Index and one of the lowest number of venereal disease cases per 100,000, we think heartbreak is short-lived here.

Did you know? Camp Pendleton, in San Diego, hosts the Heartbreak Ridge Half Marathon every year. Approximately 90% of the course is on off-road trails through the hills of Camp Pendleton Marine Corps base.

9. Phoenix, AZ

PHOENIX, ARIZONA

Average duration of failed marriages: 18.7 years
Dating services: 7
Gallup Well-Being Index rank: 44
Gonorrhea cases per 100,000 people: 106.2

The presence of Phoenix on this list emphasizes the strange connection between heartbreak and heat. Phoenix is another city that tends to have marriages that blow up quickly. Phoenix definitely has a demand for dating services also, but compared to most of the other cities on our list, it’s relatively happy, ranking 44 on the Gallup Well-Being Index.

Did you know? The cactus flower is a symbol of maternal love.

8. Los Angeles, CA

LOS ANGELES, CALIFORNIA

Average duration of failed marriages: 18 years
Dating services: 33
Gallup Well-Being Index rank: 52
Gonorrhea cases per 100,000 people: 101.2

We were surprised that L.A. wasn’t higher on the list; after all, it’s the only place in America where getting a divorce could be “a good PR move.” But what helped land the City of Angels on the list is its whopping 33 dating services.

Did you know? After 17 seasons of The Bachelor, which is produced in Los Angeles and features a myriad of exotic locations, only two of the couples are still together.

7. Dallas, TX

DALLAS, TEXAS

Average duration of failed marriages: 17.1 years
Dating services: 13
Gallup Well-Being Index rank: 61
Gonorrhea cases per 100,000 people: 120

The marriages in Dallas are some of the shortest, which is a big reason it made the list. On top of that, the city is only a little better than middle-of-the road in terms of well-being. Dallas’ 13 dating services suggest that lots of folks here are looking for love, but with 120 cases of gonorrhea per 100,000 people, they may be looking for it in all the wrong places.

Did you know? The U.S. Army established Love Field, now a major hub for Southwest Airlines, on October 19, 1917. The facility included some hangars and a grass landing strip.

6. Baltimore, MD

BALTIMORE, MARYLAND

Average duration of failed marriages: 18.7 years
Dating services: 5
Gallup Well-Being Index rank: 88
Gonorrhea cases per 100,000 people: 109

With five dating services and a lot of relatively short marriages, Baltimore lands #6 on our list. This city also lands on the lower half of the well-being rankings, and there appear to be plenty of folks whose exes have given them more than just heartache here.

Did you know? Famous writer H.L. Mencken courted Sara Haardt for seven years while in Baltimore, according to the Baltimore Sun. The romance was rocky, partly because Mencken lived with his mother.

5. Houston, TX

HOUSTON, TEXAS

Average duration of failed marriages: 17.1 years
Dating services: 8
Gallup Well-Being Index rank: 74
Gonorrhea cases per 100,000 people: 124.7

With an average high of 93F in the summer, Houston is literally a hot mess. Love doesn’t last long in this town, after all, and with an infection rate second only to San Antonio, let’s say that heartbreak here sometimes leaves a mark. With a middle-of-the-road rank on the well-being index, it makes #5 on our list.

Did you know? Romance Writers of America, a trade association of over 10,000 romance writers, is headquartered in Houston.

4. Riverside, CA

Average duration of failed marriages: 18 years
Dating services: 4
Gallup Well-Being Index rank: 152
Gonorrhea cases per 100,000 people: 70.4

If you just looked at the Gallup Well-Being Index, pretty much everyone is miserable in Riverside—the city ranks dead last on that list. Divorces occur relatively quickly, too. One thing Riverside has going for it: the infection rate is one of the lowest in the country.

Did you know? One of the most popular movies to end in heartbreak, Gone with the Wind, first previewed at the Fox Theatre in Riverside on September 9, 1939.

3. New York, NY

NEW YORK, NEW YORK

Average duration of failed marriages: 21.9 years
Dating services: 28
Gallup Well-Being Index rank: 100
Gonorrhea cases per 100,000 people: 110

New York is pretty average in terms of marital breakups, but with 28 dating services, it stands out in terms of the demand for finding a better match. The Big Apple probably needs to eat more apples and less apple pie, too – it ranked only 100 out of 152 in well-being.

Did you know? On the evening of February 14, the top of the Empire State Building glows red and pink, to celebrate the lovers below – and inadvertently annoy those who are alone on the big city streets.

2. Miami, FL

MIAMI, FLORIDA

Average duration of failed marriages: 19.9 years
Dating services: 26
Gallup Well-Being Index rank: 119
Gonorrhea cases per 100,000 people: 93.3

The lesson behind Miami is that sand, sunshine, and beaches don’t always prevent heartbreak. Marriages tend to blow up relatively quickly in the Sunshine State, and Miami is squarely in the bottom quintile of well-being. When it comes to venereal disease, they’re a little healthier “down South,” and with 26 dating services in town, there are plenty of people looking for love.

1. Chicago, IL

CHICAGO, ILLINOIS

Average duration of failed marriages: 21.3 years
Dating services: 16
Gallup Well-Being Index rank: 87
Gonorrhea cases per 100,000 people: 150.5

Some call it the jazz capital of the world; others call it the basketball capital of the world. But Chicago is also the heartbreak capital of the world by our measure. With 16 dating services, there are a lot of people looking for love in the Windy City. But choose your partners carefully as chances are high you could end up with a broken heart or even worse – a case of gonorrhea.

You could look at this list two ways. If you’re broken-hearted and believe in “misery loves company,” you may find some kinship in the residents of these metropolitan areas. Or – and this is assuming you’re careful, of course – you could find some single people.

Phoenix AZ Is in The Top 10 Cities with The Most Heartbreak