How to Pick Up Cougars Online

Online Personals sites are where you can meet the lion’s share of older women for sexual purposes. I suppose you can still log onto AOL or Yahoo Chat, find a cougar online, and make it work, but I think those days are pretty much over at this point. It’s much more efficient to use an official service.


Sites to Avoid:

Now you’re going to have to be a little careful when looking at sites to find cougars. If you use the wrong ones, you could at the least have your time wasted with fake web-cam girls and spyware. At worst, you could get robbed by a thug that is not of cougar-age or female. Heed these warnings carefully:

Craigslist.org: There are women of all ages looking for sex on Craigslist. It’s a good place for them because no photo is required. They can remain anonymous. At the same time, this anonymity yields opportunities for scammers, thieves, and all sorts of shady people to try to rip you off. It’s not an uncommon story for someone to invite a woman over from Craigslist and then be greeted by her and two men with bats who proceed to mug him for everything in his apartment. If you must use Craigslist, have all of your meetings in a public place away from your house…which kind of defeats the point of a hook-up invitation, doesn’t it?

Fling.com: This is an explicit booty-call site, which leads to similar problems you might find on Craigslist. If it’s too good to be true, it probably is. I know men who have had success on this, but there are a number of red flags. Proceed with caution.

AdultFriendFinder.com: You probably won’t get robbed on this one, but there are so many spam bots, you’ll be hard pressed to find a woman that exists beyond her profile page. Most likely you’ll be redirected to porn sites. Avoid this one.

Sites that Work:

Basically any legitimate “relationship focused” dating site is great for finding cougars. The one exception would be eHarmony. You can use it, I suppose, but the set-up for meeting women on there is so relationship focused that it can be strange to try to convert your meeting with the cougar into a purely sexual relationship.

There are dozens of dating sites to choose from, and here are my favorites:

– Match.com
– Jdate.com (For Jewish People)

– AmericanSingles.com
– PlentyofFish.com

NEW! – CougarLife.com. This is a site explicitly set up for matching up older women with younger guys. I have looked at it and it seems pretty good, but I have not tested it enough to give it a full recommendation at this time. Use at your own discretion and report back your results!

These are all paid sites with the exception of Plenty of Fish. I think you’re better off using the paid services, because you’re less likely to run into “tire kickers” who just log on once in a while and never really meet anyone. Also, Plenty of Fish is one of the lowest-ranked dating services in terms of income and education levels, so if you value sophistication in your women, you may have a harder time finding a cougar you actually want to hang out with.

The one advantage Plenty of Fish has over the others is that you are 100% sure a woman can read your email if she chooses to. I can’t say that about any of the paid services, unfortunately. Whether a woman can read your message is critical to your success, so I’ll address that later in the post.

Your Profile

Your dating profile should not give any clues that you want to talk to older women. There will likely be a part of your profile where you can put a preferred age range. Make the preferred range of your partner within 4-5 years of your own age in either direction. If you’re 27, make your age range between 23 and 32. Don’t make the numbers exactly 10 years apart (i.e. 23-33), or it will look weird.

You may wonder why it’s not a good idea to make your age range 21-45, or even 35-45 if you’re looking to score with older women.

The main reason why you don’t want to have the cougar’s age in your “preferred range” is because when an older woman looks at your profile, she will assume that you’re looking to actually date cougars. This will make the cougars who want flings assume you want something serious and they will not want to meet up with you. Additionally, having your age range go up to 45 will bring you older women who actually expect candle-light dinners from you, complete with walks on the beach and dancing in the moon light.

Equally as important, a cougar wants to believe that she’s the exception to the rule. In her fantasy, you are on that dating site specifically to meet 23-28 year olds, and then saw her and got turned on. She imagines you saw her and thought, “Wow she’s freaking hot for a 39 year-old,” and had to violate your original plans in order to talk to her.

She doesn’t want to be one of many cougars you’re hitting on, so this is another big reason why having a younger stated age range in your profile is important. She gets more “bragging rights” to her friends if you are a guy who supposedly doesn’t even like older women most of the time.

For the rest of your profile, simply just express your personality in the best way possible. Don’t try to say impressive things about yourself. Just talk about your hobbies, your passions, your goals, etc. If you legitimately have interests in the “Cougar Topics” mentioned earlier, include them in your profile. If the cougar and you have these things in common, she’s likely to be much more receptive when you contact her.

Have at least three pictures up. There is a point of diminishing returns as you go beyond three. If you have seven pictures, you’re not getting any more mileage, and risking that you have a dud in there that will make her say “Oh he’s hot, *clicks on bad picture+ eww… maybe not.” Just pick your best three to five pictures. If you have some cash to spend, you can get a professional photographer to take your picture in low resolution for online portraits. You can usually get four pictures, wearing different outfits, for $85-100. This can really help your response rate. Many otherwise good-looking men take pictures that are absolutely awful for getting women to return their IM’s and emails.

If you have a resilient enough ego, you can put your pictures on a site like HotorNot.com, and let the world vote on which pictures make you look good. You can put pictures up, and you’ll get a rating between 1 and 10 (10 being the best), based on your averaged scores. I’ll warn you, the people who vote on that site are often mean-spirited, self-hating, and cruel. No matter how good you look, you’ll get a lot of 1’s. You may put a picture up that you think is great and then get an average of 4.3. The site owners try to adjust the rating to rebalance this, but you will still see the breakdown of your votes, including a lot of 1’s. If this will break your heart, just ask friends about which pictures look best for you.

On your profile, there’s also likely to be a field to fill in for what kind of woman you are looking for. You can really put anything in here, but don’t be too specific, especially in areas that women will likely doubt themselves in. Don’t put “athletic,” as a lot of women only hit the gym a couple times a month and think they’re fat. Don’t put “artistic” or “musical” or anything that requires talent or training. You can put “educated,” but this will weed out women who feel that their BA is not enough.

If you want good examples of what kind of descriptions to put in this part of your profile, look at some Horoscope personality descriptions. I don’t mean the newspaper predictions, but the actual descriptions of what Libras or Virgos are like. These descriptions are intentionally vague so anyone can feel like they’re being described. When you have a description like this, your cougar can read what you wrote and say “Hmm… that sounds like me.” Do this from a real book in Borders, rather than looking it up in a website. While some websites are good, the truth is that anyone can put up a shitty horoscope site. If the author got published, there’s a good chance they write well enough to serve our purposes here.

First Contact: Instant Message

Whatever dating site you use, your best bet is to connect over instant message for your first contact. If your site lets you connect over IM, you can speedily work the get-to-know-you process, and possibly have her over the next night to hang out. I said to ignore the age objections in bars, but online it’s a bit different. You can embrace the objections when they come up, or answer them with indifference, but you can’t simply pretend they’re not there. Often taking her objection and running with it can take you very far.

There was one older woman I was talking to on a dating site, who after a few instant messages said, “Boy, you’re too young for anything but a fling,” and closed her IM window. (This was a site that lets you know when someone leaves the conversation).

Instead of arguing, with her, I replied with, “Maybe that’s what I want.”

You could see in the IM window, “User has re-opened IM session,” and she immediately typed, “Oh really? Do you like to eat pussy?” This began a very focused conversation of where this relationship was going, resulting in an invitation to her house the next day.

Your conversations will rarely be that explicit, and it is not a good idea to try to push it in that direction while online. Unlike meeting someone in a bar, it can be a fine line to walk when you clarify your intentions with a cougar online. These women get bombarded with instant messages and emails where clueless horny guys say “WANT 2 F&#K?” or send them unsolicited pictures of their cocks. Women get so many emails and IM’s on these services in general that they can’t help but quickly categorize the men that contact them. You want to avoid the “Horny Idiot” category at all costs.

You will get numerous age-related questions, such as “Do you like older women?” or “Aren’t I too old for you?”

Remember that questions like this are not the same thing as saying “You’re too young for me.” It can be subtle at first, but there’s a huge difference between a woman thinking you’re out of her age range and her being concerned that she is out of your age range.

Online, a lot of women are looking for that special relationship and have often felt like the outside world has failed them in bringing suitable mates. There may be some real self-esteem issues at work. This is not always the case, as you will find some very confident women as well.

The dynamic is very different online than at a bar. She will be more likely to see herself as under qualified for you than the other way around.

You may wonder why she wouldn’t jump at the chance to hang out with you if she sees you as the better catch out of the two of you. The reason is that while women face romantic rejection far less than men do, it stings them a lot harder when it happens. Even worse, she can feel rejected post-sex, which is a phenomenon that doesn’t really happen to guys.

Here are the worst-case scenarios that can happen to her if she meets you and is not up to your specifications for your preferred woman:

  1. She can show up and it will be awkward
  2. She can show up and you quickly end the date and not call her again
  3. She can show up and you have sex with her and decide she’s not worth even screwing a second


Even the situation of showing up to an awkward date can bring up a ton of resistance for a woman.

To take care of this, your job is to let her know that her age is either a non-issue or an actual asset. In my experience, it’s safer and more consistent to make it a non-issue.

If she says, “Aren’t I a bit old for you?” you can say, “I’m not really worried about that.” Online, you should give the impression that you treat age like nationality and religion. If you’re a non-religious Christian and a cute Asian girl said, “You know I’m Buddhist, right?” you would say the same thing. “That’s not an issue for me.”

When you make the age thing a non-issue, you give the cougar a lot of plausible deniability about what’s going to happen when she meets you. On some level she knows it would never work between you two, and that a hook-up is the most likely happy ending for the night. On another level, she thinks, “Why not? I’ll give it a shot.” This is what she’ll be telling her friends when she leaves for the date, and what she’ll be telling herself as she drives over. Unlike men, women often need a “cover story” for why they’re going to meet you for a hook-up, as well as for why they’re going into your house or into your room. This may be hard to understand at first, but a woman will often lie to herself more than any man will.

You might also get a question like “Are you trying to pick up older chicks?” or “Are you on a cougar hunt?” When a woman asks something like this, it means she’s on to your game, and putting you in a bit of a tough position. The best way to respond to something like this is to type “Hahaha” or “lol” and make a joke out of it like “Yeah, step on the boat,” or “Yeah, didn’t you hear, it’s cougar season :-P” Then say “J/k” (just kidding), and keep talking. Don’t actually say “cougar” in the joke back unless she says it first. In fact, don’t say cougar at all when talking to older women. Many will not appreciate it, and will think they’re not “of cougar age” yet.

Anyway, once you deflect a question like that with humor, she’s unlikely to push for a real answer.

You might also get questions like “What are you on this site for?” and “Are you looking for a relationship?” This is not the time to play gentleman and say you’re looking for the perfect woman and that age doesn’t matter to you. Instead, be vague and relaxed, and say something like “I’m just seeing where it goes. Not in a hurry for anything.”

In general, the more vague you make your expectations sound to women, the more she can relax her own expectations.

After about fifteen to twenty minutes of talking, you should ask for a phone number. You’ll get a lot of points for having some cockiness and swagger in your phone number request. Cougars are often dating soft, weaker men their age who have all but lost their youthful swagger. It will be quite charming for them to experience this confidence again.

Here are some ways to ask for the number:

“So, I think I should give you a call.”

Or the reverse…

“So, I think you should give me a call.” She’ll say “Wait a minute, don’t you have this backwards?” And you say “Ok, I’ll play it old-fashioned. I want to call you. What’s your number?”

First Contact: Email

I hate email, in terms of online dating. The owners of the dating sites intentionally trick you into thinking there are more available women on the sites than there are. Most dating sites that offer “free memberships” merely let the “free” users put up a profile and exchange “Winks” and “Flirts,” without letting them read or respond to email. This lets the dating sites pad their membership statistics with unreachable women.

The thing I like about instant messages is that many pay services will let you instant message non-paying members. This helps you beat the competition from men who are emailing these women but can never reach them. Any of the dating services created by Spark Networks (AmericanSingles, Jdate), have a robust instant messaging system than can help a lot with getting quick contact with cougars.

If you’re putting a lot of thought into your emails to women, you will be wasting a lot of time, since the sites do not let you know who is a paying member and who isn’t. The only way around this is to create generic emails that you can send repeatedly to cougars one by one. You will get a better response rate if you can mention at least one aspect of her profile. It could be anything, such as the hat she’s wearing, a band she said she liked, or a country she visited. Having that one piece of information lets her know you actually looked at her profile instead of just mass mailing (which we are pretty much doing). Making the email look more personalized helps with cougars even more because they don’t want to think you sent them a mass email by “accident” because you didn’t notice her age.

At the same time, it takes a lot longer to look through every profile for something to say before you send something else. Here’s a sample two line email I like to send out.

“Hey there,
I saw your profile and wanted to say hi. How’s your week going? –Gary”

If you just mass an email like that (and please, use your own words), then you’ll have a fair amount of women open it, look at your picture, and decide if they want to write back. If you want a better response rate and have a little more time, you would add a sentence or two in the middle, acknowledging part of her profile.

“Hey there,

I saw your profile and wanted to say hi. Do you take yoga downtown? I just started and it’s so hard. How’s your week going?


I suggest you try both approaches and see which pans out better. The more photogenic you are, the easier time you will have with the mass emails. Once a cougar writes back, just make some nice conversation back and forth and ask for a phone number. You are unlikely to really get age objections and discussions over email.


Whether you’re on instant message or email, you will have to get on the phone with her at some point. Interestingly, once you’re on the phone, you’re actually in pretty good territory. It’s rare that you will get a cougar on the phone with you and not be able to meet up with her. Once you meet up, anything can happen, but the phone is pretty safe ground to schedule a meeting on the first call.

A lot of you may be wondering, “What do I say?” This is where you really just have to be normal enough to hold a decent conversation over the phone. That’s seriously all you need to do. Talk about your day, your passions, your hobbies, your music, and ask about hers. Don’t talk dirty, though you can be flirty. Whatever you do, don’t engage in phone sex or anything of that nature. Also, take some time getting to know her before scheduling a meeting.

Talk with her on the phone for about twenty minutes before making an invitation. Say, “So I’m thinking you should come over at 8pm tomorrow and we can hit a happy hour at Jobo’s Tavern.”

For your invitation, saying “we should” or “you should” is a great way to ask. It’s a lot better than beginning with “Would you like to” or “Do you want to.” You want to show as much certainty as possible when inviting her out.

If she’s busy at that time, try to schedule another day around it. If she doesn’t have a good time available around your original invitation, don’t push it. Just say, “That’s ok, we’ll try again another time.” Stay on the phone with her about five minutes more, and then let her go. Send her some friendly/flirty texts over the next couple days.

One thing you have to make sure of is to not agree to a half-hearted, “I’ll let you know tomorrow.” If you invite her out for Wednesday, never let her tell you she’ll text you Wednesday morning or when she gets out of work to let you know. It puts you in a very weak position and the underlying implication is that you have nothing going on in your life, while she is a busy socialite/professional who needs to manage her schedule more carefully.

If she tries to pull something like this, say, “Oh, if you might be busy, let’s just wait until we’re more sure you’re free.” She won’t argue this, and will even respect that you held your ground.

The only time I let a woman get back to me about a date is if she says “I’ll let you know tomorrow” and the date is at least 24 hours away from when she plans to let me know. Even this is pushing it, and I recommend you stick to firm answers on your invitations. Weak plans equal no plans.

However, there is one technique I like to use if a woman wants to let me know the next day. Bear in mind, I do this not expecting her to show up.

Suppose I invite a cougar out for Tuesday, and she’ll say “I’ll let you know tomorrow.” I might agree, and then assume she’s not coming. I don’t call or text her the next day at all, but during the time we would have been out, I send her a text talking about something fun I’m doing. I might say “At Kareen’s Pub, having a blast, you?” Don’t mention that you two were supposed to be on a date. She will think in her head, “Wow, I could have been out with him right now.” Also, if you text her something like this, make sure the venue you mention is not the same one you invited her to.

Once again, scheduling a date is super simple. Just make sure you decide where it is and what you’re doing, not letting her take the lead. Where you will take her will be covered in the next blog.

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