• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

Aol and Yahoo: Time to put a ring on it

By
Scott Olster
Scott Olster
Down Arrow Button Icon
By
Scott Olster
Scott Olster
Down Arrow Button Icon
November 9, 2010, 12:21 PM ET

After years of flirtations, Aol and Yahoo, or at least their bankers, seem to again be talking about a union. Our business relationship advice columnist has had enough, and says they should seal the deal already.

By Chadwick Matlin, contributor



Dear Mergie:

I am at a loss. Not, for once, of my money. (I’ve had a great few months.) I’m at a loss of what to do about somebody I like. It’s not that she doesn’t know who I am—we’ve known each other for years and worked our way from friend to enemy to frenemy and all the way back again. She’s great—underappreciated by everyone else, but she comes with a good legacy. She’s just had a rough go of it these past few years.

Recently I started flirting with her again, not with any real purpose, but not with any real restraint either. It just feels so good to be a player. To feel like my life could change with one chance meeting in a corner office or boardroom. I’m not even sure if she wants me — like I maybe, sortof, but not really want her. But I think we have a lot in common, and we could really complement one another’s personalities. We’re both figuring out how to live in this new, crazy, mixed-up world that surrounds us. It feels like we could be great partners in existential angst.

But how will I know when I know, you know? I’ve paid people to be my friend and give me advice, but don’t I need to make this decision for myself? When will I be able to take the plunge and stop pussy-footing around?

–A.O.L., 21, New York

Dear A.O.L (AOL) :

You’re still hung up on this Yahoo! (YHOO) ? I looked through my files and I saw that you sent me more or less the same letter two years ago, when you were living still living under your parents’ roof in Dulles, Virginia. (I’m assuming this “Time Warner” (TWX) guy you mention was your legal guardian?) Now you’re on your own and you’re still flirting single-mindedly. Proof that you really care. Or that you’re a stalker.

Now, it’s possible you’ve written me this letter for the same reason you may have hired those new friends: to get your yahoo to pay attention. Not the worst idea; proclaim your interest publicly and it could be seen as a romantic gesture. It’s no Say Anything, but it’s a start.

But this has gone on long enough. I did some research and found that you’ve intensified your I-love-her-I-love-her-not routine in recent months. In October you talked to others about the best way to acquire what you desire, because you aren’t big enough to do it all by yourself. And when people ask, you’re all too happy to name-drop that you’re interested in her if it makes sense, but that you could also sidle up to others too. Nice try, playing coy.

But I’ve read up on your yahoo, too. And it doesn’t seem like she’s eager to get together. In fact, she bought a can of mace from Goldman Sachs in case you try and make any unwanted advances or hostile takeovers.

Yet, my advice is this: Don’t be deterred. To answer your original question: How will you know when you know? That you think you may already know means you know. That’s how love works. The confusion is the proof. QED.

The time is right to make a move. Your house is in order. As you said, you’re making money again, and even have enough lying around to buy yourself some expensive, delicate baubles. You need what Yahoo can offer you now: more attention, more purse strings, and more energy to compete for supremacy.

Now, you may not have the perfect relationship from the start. The power differential will be steep, and both of you may have to get rid of a few people things to make it work. Your yahoo is going to be the breadwinner and then some. Which is why she may not sign on for a traditional partnership; if she won’t go into this willingly, maybe you can pitch a political marriage, one of convenience for both parties. Partner first, procession down the aisle, later.

So stop flirting and start committing. Even though you’re 21, now’s no time to be a bachelor out there.

10-k (ten thousand, that is) kisses,

Mergie

[cnnmoney-video vid=video/technology/2010/10/14/f_bst_aol_yahoo.fortune/]

About the Author
By Scott Olster
See full bioRight Arrow Button Icon

Latest in

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in

dario
AIWhite House
White House chief of staff to meet with Anthropic CEO about dangerous new Mythos model, official says
By Josh Boak, Matt O'Brien and The Associated PressApril 17, 2026
3 hours ago
broker
EnergyMarkets
Oil is back to early war days, S&P 500 jumps to all-time high
By Stan Choe and The Associated PressApril 17, 2026
3 hours ago
Photo of Donald Trump (left) and Pete Hegseth (right)
Economynational debt
Something is different about Trump’s $1 trillion war on Iran and its stress on the national debt, Harvard Kennedy scholar says
By Sasha RogelbergApril 17, 2026
4 hours ago
Huel Shake Review (2026): Expert Approved
HealthDietary Supplements
Huel Shake Review (2026): Expert Approved
By Emily PharesApril 17, 2026
4 hours ago
Half of Iran’s workforce faces unemployment risk as the U.S.-Israel war’s ‘hidden target’ was the labor market, economist says
EconomyIran
Half of Iran’s workforce faces unemployment risk as the U.S.-Israel war’s ‘hidden target’ was the labor market, economist says
By Jason MaApril 17, 2026
4 hours ago
Exclusive: Adam Silver on winning the Edison Achievement Award: ‘Sports remind us that some of the most important forms of innovation are human’
Arts & EntertainmentSports
Exclusive: Adam Silver on winning the Edison Achievement Award: ‘Sports remind us that some of the most important forms of innovation are human’
By Catherina GioinoApril 17, 2026
5 hours ago

Most Popular

Pope Leo warned the world is in ‘big trouble’ if Elon Musk becomes the first trillionaire
Success
Pope Leo warned the world is in ‘big trouble’ if Elon Musk becomes the first trillionaire
By Preston ForeApril 17, 2026
14 hours ago
A world going broke: IMF says America's $39 trillion national debt is actually a global problem—and AI may be the only rescue
Economy
A world going broke: IMF says America's $39 trillion national debt is actually a global problem—and AI may be the only rescue
By Nick LichtenbergApril 16, 2026
1 day ago
Jeff Bezos pledged $10 billion for climate change. With the 2030 clock ticking, his wife, Lauren Sánchez Bezos, is leading the charge to spend it
Environment
Jeff Bezos pledged $10 billion for climate change. With the 2030 clock ticking, his wife, Lauren Sánchez Bezos, is leading the charge to spend it
By Sydney LakeApril 15, 2026
2 days ago
MacKenzie Scott is bypassing the Ivy League and rewriting the $79 billion higher ed playbook by giving to HBCUs and community colleges
Politics
MacKenzie Scott is bypassing the Ivy League and rewriting the $79 billion higher ed playbook by giving to HBCUs and community colleges
By Sydney LakeApril 16, 2026
1 day ago
Germany already told its workers to ditch four-day weeks and work-life balance. Now the government wants to cut their pay for calling in sick, too
Success
Germany already told its workers to ditch four-day weeks and work-life balance. Now the government wants to cut their pay for calling in sick, too
By Orianna Rosa RoyleApril 16, 2026
2 days ago
NYC Mayor Zohran Mamdani points at Ken Griffin's $238 million penthouse on tax day: 'Today we're taxing the rich'
Personal Finance
NYC Mayor Zohran Mamdani points at Ken Griffin's $238 million penthouse on tax day: 'Today we're taxing the rich'
By Catherina GioinoApril 16, 2026
1 day ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.