10 of the Biggest Online Dating Mistakes

Cosmo and I put our heads together to come up with the worst things we baby boomers do on dating sites, and on first dates and beyond. Some we’ve done ourselves . . . sometimes with disastrous results.

1. Not using online dating sites at all.

If you really want to up your chances of finding your ideal partner, you MUST go where you’ll find the biggest pool of singles over 60 who are looking. You should be spending most of your dating time using these sites, unless you have an enormous network of people who will help you find your ideal partner.

Millions of people are on dating sites. In fact, we (singles 55 and over) are the largest growing segment on dating sites.

Sure, you’re going to find what some unkindly refer to as”losers” on the sites, but there are also plenty of great people like you, looking for love.

Online dating should be the biggest part of your dating strategy, but don’t neglect in-person networking with everyone you know . . . letting them know what you’re looking for and asking if they know anyone.

And don’t neglect groups like Meet-Up, where you may find like-minded, single people for various activities.

Read more about online dating sites and the ones we recommend in Top 10 Best Online Dating Sites for Over 60: How To Choose and Use Them.

2. Not knowing who your ideal partner is.

I strongly urge you to take the time to identify (or target) the right kind of person for you.

Think of this as step one in smart dating over 60.

You’ll save yourself a lot of heartache and time by setting the criteria and deal breakers, before you start proactively dating . . . or pausing to do this work even if you’ve been dating for a while.

When you know who you’re looking for, you’ll be better able to:

• Write the narrative section of online profiles, to attract the right people.
• Differentiate yourself from the sea of other daters competing against you.
• Generate chemistry for you as a person and potential partner.
• Weed out prospects who are a bad match for you.
• Save time and reach your goal of finding your ideal partner faster.

3. Pegging your ideal partner way too specifically.

On the other hand, you can go too far with targeting.

If you will only consider dating people who fit a highly specific list of criteria, you may never find someone.

Cosmo half seriously was stuck on this impossible combination of must-haves in women he would date. These were things that he himself was involved with, or that described him at the time:

• She must be a pilot and own her own plane.
• She must go to Mass every day.
• She must be a small business owner.
• She must own her own home.
• She must have a nice car.

Luckily, he quickly realized early in the game – and before meeting me – how narrow and foolish his thinking was.

Although I do own my own home and happen to be a small business owner, I don’t meet the first two criteria. And I have a 20+ year old car, but it’s a classic and cherry.

Yet I’m Cosmo’s ideal partner (and vice versa, of course).

4. Putting your real name or any other identifying information about yourself on your profile.

Maybe this is an obvious “don’t”, but I came across many men who used their full names for their profile name or handle. Some also included where they worked or other specifics in the narrative section that could be used to more deeply identify them.

This was great for me. I could Google their names to find out more about them, before considering reaching out to them.

But not so smart for the men. Women can be catfish, predators and scammers, too. With someone’s full name and other bits and pieces of information, it may be possible to determine your location, and maybe even steal your identity.

Women AND MEN need to be careful on these sites. Everyone is vulnerable.

5. Posting unrealistic, glam photos on your profile.

If you’re seriously dating, you MUST include at least one photo. Several are better, showing you in different locations, doing different things, but with a clear view of your face.

Take and choose photos that represent you well. You don’t want your dates to go into shock when they first see you.

Photos to avoid:

• Headshots that are highly touched up, with perfect lighting, that don’t reflect what you really look like.
• Headshots of you overly made up, if you’re a woman.
• Photos taken more than 5 years ago. I’ve actually seen profiles with high school photos!
• Only full body shots, taken at a distance, so you can’t see your face well.
• Group photos in which you can’t be distinguished from the rest.
• An abundance of photos showing your car, pets, house, or something that isn’t you.
• Pictures of the humongous fish you caught.

6. Venting your anger at others (exes, political figures, etc.) in your online dating profile . . . or making dates with those who do this.

This often includes loading the content in the narrative sections of online profiles with ALL CAPS.

I learned to steer clear of men whose profiles showed their anger or animosity . . . especially directed at their ex-wives or ex-girlfriends. These men were clearly not over those soured relationships and would bring unresolved issues into a new relationship.

I also avoided men who vented about their online dating experiences on their profiles. Typically these men had been in the dating game too long, or were too picky, or were too jaded to be open to accommodating a new person in their lives.

7. Reaching out to someone for the first time with a stock email message.

One of my pet peeves was getting first emails from men that merely said:

“Let’s meet for coffee.”

It happened a lot.

First, it’s not a good idea to lead with a command (“let’s”). And I had to wonder how much effort he would put into a relationship if, from the get-go, he wasn’t willing to invest time in his introduction to me. And, I wondered if he had even read my profile, or was just attracted to my photo.

You’ll be much more likely to get a response if you take a few moments to personalize each first email, based on what you see in their profile. Try something like this:

I enjoyed reading your profile. I see you’re interested in [insert something you read in their profile]. I am, too. In fact, [insert a tidbit about the item].

Let me know if you’re interested. Hope to hear from you soon.

Have a great day!

[your profile name or handle]

Keep it brief, but personal and engaging.

8. Holding out for someone who sounds great, but keeps avoiding meeting in person.

If someone you’re interested in is resistant to moving on from emailing (or texting) to phone calls, or moving beyond that to meeting in person, things probably won’t work out.

Their resistance can mean any number of things, including:

• They’re not who they appear to be in their photos.
• They’re married or in a so-called committed relationship.
• They’re not ready or interested in seriously dating.
• They’re scammers who will patiently lure you in and hit you up for money.
• They get some kind of sick pleasure (maybe sexual pleasure) from phone calls with you, and that’s all they’re interested in.

I would hate for you to zero in on someone like this, at the expense of anyone else. You’ll waste precious time and may get hurt.

People can come across beautifully via email and/or can be great conversationalist via phone, adept at making you feel like a million. If it’s been more than a few weeks or a month, you really need to question why they’re turning you down for a meeting.

By the same token, if you want to drag out the email and phone time without meeting people in person, you may not be ready to date.

9. Going out to dinner – especially at a romantic restaurant – for the first date, no matter how great they sound.

I wrote about a fiasco first date where I foolishly did just that, in The Worst First Date I Ever Had . . . It didn’t go well.

Unless you’re extremely lucky, you’re going to have many first-and-only dates with people. Try not to go into each one hoping she or he is “The One”.

Just think of it as meeting someone new, and a learning experience. Every date you go on – with your mind open – will help you better understand yourself and who your ideal partner is.

Remember, it’s just one date . . . maybe an hour or so of your day. If things don’t work out, no big deal.

If you compound the stress and high expectations by meeting at a romantic spot, you may be building up for an awful letdown. Why take that risk?

Best plan for a first date – go for coffee in the afternoon, when it’s still daylight and you’re not walking into a dark parking lot with them after the date.

It can be a quick date, if things don’t go well. Or you can extend it, if you’re both grooving on it.

And, for obvious safety reasons, don’t let this person you know almost nothing about pick you up at your house for a first date. They’ll know where you live and you’ll put yourself at serious risk by getting in the car with a stranger. Things can go real bad, real fast.

10. Not being clear early in the game about your intentions.

Are you only interested in quick, sexual hook-ups?

Do you want to find someone for companionship or friendship only – no sex?

Or, are you looking for a “forever” romantic partner with all the bells and whistles?

Whatever you want is okay, and these are all good reasons to be on the dating sites. You’ll find like-minded people.

But don’t pretend you’re okay with one-night hook-ups, thinking maybe they’ll turn into the forever love relationship you really want. It probably won’t, and you will have wasted all that time.

I always appreciated it when men stated their preferences clearly in the narrative section of their profiles. Since I fell in the category “looking for a ‘forever’ romantic partner with all the bells and whistles”, I could easily rule out those guys who fell into one of the first two categories above.

Don’t mislead about, or cover up, your true intentions. Be up front within the first few dates. It will come out soon enough.