Lounges VS Restaurants: The Cougar Dating Smackdown

I would guess that 95% of all first dates start at either a restaurant or a bar. Sure, there are other places you can take a date, but chances are you’re considering one of these 2 popular options. They each have positives and negatives, so let’s weigh the pros and cons and determine the best place to take a Cougar on a first date.

Dinner Date Pros

  • Long waits for a table and food to arrive provides a perfect opportunity to chat and get to know each other.
  • If the food is good, she’ll leave happy.
  • Laid back atmosphere, which makes for a comfortable evening.

Lounge Pros

  • No wait for tables, food and drink orders, or for food to arrive.
  • Easier to escape more quickly in the event your date is lame.
  • Easier to leave more quickly to take her back to your place.

Dinner Date Cons

  • Too much time spent waiting for a table, waiting for food, and eating.
  • More expensive than just going out for a couple of drinks.
  • Harder to go from date to bedroom.

Lounge Cons

  • Often too crowded and loud to hear each other speak.
  • If you drink too much, you’ll begin to act stupid.

Let’s Settle the Debate…

You’ve seen the pros and cons. Considering each of the factors listed above, taking her to a lounge is, far and away, the best first date option. Yes, a lounge can be loud and crowded. That’s why you take her AFTER dinner, before the bar becomes packed. Meet her there around 8:00 PM. Have 1-2 drinks, work your game, and get the hell out of there and back to your place.

You can find the best place to take a Cougar on a first date

You can find the best place to take a Cougar on a first date

Why am I opposed to dinner dates? Because they’re too time consuming and rarely result in getting laid. Eating a nice meal often wears us down physically. Dinner is usually the first stop before going home, but rarely the last. She’ll probably want to go have a couple of drinks after dinner. So why not just skip the dinner and meet for drinks?

Dinner dates

Dinner dates

Cougar Date Story #4: Proof that Nerdy Guys Can Hookup With Hot Women

This Cougar dating story doesn’t involve me. It involves my best friend, Greg. About 6 months ago, I approached Greg about signing up for an Internet dating site. He’s had 1 girlfriend in his life, and that was about 5 years ago. Let me give you some background on Greg. He’s 26, never married, no kids, had sex only a handful of times in his life, has a good paying job, is smart, isn’t very good looking, and lacks confidence. That’s not a good combination to have if you want to get laid – especially with Cougars.


I had originally intended on helping Greg sign-up for a regular Internet dating site, where he could meet women his own age. So we got him signed up for PassionSearch.com. He had no success attracting 20-something women. I didn’t even think about having him go after Cougars. But after a few weeks of attempting to find him someone, I was ready to just give up. Women just were not digging him. That’s when I asked him what he thought about dating older women. I didn’t even know this, but he said he had always fantasized about being with an older woman. PERFECT!

You can help sign-up for a regular Internet dating site: PassionSearch.com

You can help sign-up for a regular Internet dating site: PassionSearch.com

Since I’m an expert with Cougars, I figured I would be able to better help him meet someone. The first few days were a little rough. He didn’t get much response. But then, out of nowhere, a gorgeous lady contacted him. She sent him an email that mentioned how interesting he seemed in his profile. She didn’t even mention his appearance. She seemed willing to look past that.

I sat next to him as he chatted with her via Instant Messenger. I even helped him out with many of the answers. Then I told him why I was telling him to say what I was telling him to say. After a bit, he was starting to catch on and my help was no longer needed. This woman got my shy, nerdy friend to open up. And once he started to open up, he became quite confident. He really does have a great personality, but he is too afraid to let strangers know of that personality.

 You can chatted with her via Instant Messenger

You can chatted with her via Instant Messenger

Dude absolutely nailed it with this gal. Within 2 hours of conversation, they had a date set-up. I didn’t even tell him how to ask for the date. He just did asked with confidence. They agreed to meet that weekend at a Martini Bar in town. I was ecstatic but I knew I better calm my enthusiasm until AFTER the date. He still needed to impress her in person.

When he left my place to go meet her, I was probably more nervous than him. I really didn’t know what to expect. An hour after he left, I somewhat expected a call from him saying that she ditched him. That didn’t happen. In fact, I didn’t even hear from him until the next day. Either he was pissed off and didn’t want to talk about what went on. Or he was getting laid. I hoped for the latter, but expected the former. It turned out to be the latter. He ended his dryspell and proved that even nerdy guys can hookup with hot Cougars if they know what they’re doing.

 Guys can hookup with hot Cougars i

Guys can hookup with hot Cougars i

Three Things to NEVER Talk About on a First Date With a Cougar

I could go on and on about the things you should talk about with a woman on a first date. But that will only get you so far. It’s equally important to know the things no guy should EVER talk about with a Cougar. For this post, that’s exactly what I’m going to do. And, yes, I have made the mistake of bringing up these subjects on first dates. Let’s just say the dates didn’t end as I had hoped.

Politics and Religion

I always recommend sticking with more mature, sophisticated topics with Cougars than younger women. And, sure, politics and religion are somewhat more sophisticated topics than, say, sex. But there are some major problems that could arise should you bring these subjects up. Politics and religion are sensitive subjects to many people. How often do you meet someone new and start talking about your religious beliefs?

Here’s a prime example of why politics and religion have no place in first date banter. Things were going well for me and my date. We had been chatting for at least an hour before I decided to bring up my Liberal political views. Turns out she was a staunch Conservative. I made one minor comment about how I disliked George Bush because of how he handled the economy and the Iraq war and she flipped shit. One minor comment caused her to get up, tell me to shut the hell up, and walk out on me. Lesson learned!

Find First Date

Find First Date

Sex

You may not realize this but you can actually get a woman into your bed without even discussing sex. It’s true. I’ve done it many times. Sex is sort of implied when you ask a woman to come back to your place. It’s bound to happen. And, if not sex, than something sexual (i.e. blowjob, handjob, etc.).

Even though it’s implied that something of a sexual nature will happen back at your place, I still hardly make a mention of sex while we’re out. As soon as we get back to my place, my dirty side comes out. Here’s the thing about women – they’re ALL total sluts. However, they like to make men think they’re not so they’ll work to chase them. But they’re thinking about sex just as much as you are, they just aren’t so open about it at first.

About sex on the first date

About sex on the first date

No one likes a whiner. Most of us work shitty jobs. I only know of a handful of people that truly do enjoy their occupation. We go to work, punch a clock, and hate what we do. That’s just the way it is. When you’re out on a date, just shut the fuck up about your shitty job and dickhead boss. She doesn’t care. She doesn’t want to hear about it. It makes you sound whiny and negative. Keep the conversation upbeat so she’ll think you’re a positive person, even if you’re a miserable loser.

Tips for Dressing to Impress Cougars: What to Wear and How to Wear It

You know what they say – your clothes reflect who you are as a person. The very first thing a woman notices is your shirt, pants, hair, shoes, and any other accessories you have on. When you’re dating a Cougar, it’s even more important to dress to impress than with younger women. She’ll judge your personality based on how you dress.

Dressing well is all about knowing yourself and what style works best for you. What looks good on one person doesn’t always look good on another. But one thing is certain – dressing well WILL help overcome certain natural physical flaws. Some of the nerdiest guys I’ve ever met look pretty darn attractive with stylish clothes. Clothes can help compensate for a lack of lucky genetics.

Every outfit should include the following…

It doesn’t matter if you’re going for the preppy, businessman, or bad boy look, your outfit should include ALL of the following…

  • Nice looking shirt
  • Well groomed hair
  • Clean shaven face or trimmed beard/goatee
  • Nice shoes that match the outfit
  • Freshly scented cologne
  • Stylish watch, necklace, wristband, etc. (if applicable)

    Dressing to Impress women

    Dressing to Impress women

It’s not all about WHAT you wear…it’s equally about HOW you wear it…

Sure, you can pick out a great outfit. If it’s not worn properly, you’ll look bad. Again, it all depends on the type of person you’re leading her on to believe you are and what looks good on you. I almost always go for the businesslike look. I find that Cougars are almost always attracted to a man that appears to be successful. Businessmen are successful. I wear a loose fitting (but not too loose) button-down shirt and a fancy pair of jeans, along with a pair of dress shoes. Everything I wear fits me perfectly. The outfit is not too snug, nor is it too loose. I look comfortable in it.

Looking comfortable in your outfit is very important. For those of you that want to go for the bad boy look, put on an Affliction shirt (black, preferably) and a pair of jeans. Wear the shirt tight. Of course, if you’re thin, this isn’t going to be a good look. I don’t recommend thin guys to go for the bad boy look. You need to be more muscular. Muscles are associated with bad boys. The preppy look is the best way to go for skinny guys (and overweight guys). Wear the outfit a bit loose-fitting.

The preppy look is the best way to Wear the outfit a bit loose fitting

The preppy look is the best way to Wear the outfit a bit loose fitting

Cougar Date Story #3: A Double-Date Gone Horribly Wrong

One of my first encounters with a Cougar came a few years back. I’m not really sure what I was thinking, but I agreed to go on a double-date with the woman I met on PassionSearch.com, my buddy Samir (he’s a goofy Albanian dude), and her friend (also a Cougar). When my lady mentioned she had a friend that wanted to double-date with us, I thought this was the perfect opportunity to invite Samir along. I knew he had a thing for Cougars. As it turned out, this was the dumbest decision of my life. And that says a lot!


The 4 of us met up at an Over-30 Club. Basically, this is a place where mostly older men and women go to dance, drink, and hookup. It’s probably the easiest place to get laid. Unfortunately, the majority of the women under 250 pounds have fucked up teeth because they’ve done so much Meth. Occasionally, an in-shape woman that wasn’t smacked hard in the face with the ugly stick goes in there. But chances are she’s younger and not looking to hookup. It’s still a fun place to go. The music is pretty good, beer is cheap, and looking at the other patrons in the bar helps boost my self-esteem.

We arrived at the club at about 10:00. My date looked good and my friends’ date wasn’t too bad on the eyes either. So we were both happy. We gave each other the thumbs-up to show our approval for each other’s dates. After meeting, we grabbed a drink and then headed to the dance floor. I wanted to get my date in the mood. A couple of drinks and sum bumpin’ and grindin’ will do that. Things started off well. She was definitely into me and her friend was definitely into my buddy. We knew early on we were going to get laid.

Normally, if I’m on a date, I try to move the party to my bedroom as quickly as possible. I don’t want a woman to lose interest before I hit it. That didn’t work out so well on this night because it wasn’t just me and my date. I had problems getting her full attention. Since we were in a group, thdies e 2 lawere interested in chatting with both of us and each other. So this prolonged the inevitable (me getting laid). Don’t get me wrong, I was never worried about getting laid. This chick was easy and I could tell that from the beginning. But I don’t like to wait to get laid. What was I supposed to do? Go beat it in the bathroom to tie me over?

My date looked good

My date looked good

The longer you stay in a bar, the more alcohol you – and those with you – will consume. By 1:00 in the morning, we were still at the bar. But now we were all rather intoxicated. I was the most sober of the group and my buddy was in decent shape. Finally, we left the bar. There was a convenient store next door that we stopped at. I grabbed a box of condoms and some gum. The ladies went to pee (together, of course). After I paid for my goodies, I went back to the condom aisle to check on my buddy. I wanted to get going because I was ridiculously horny. So horny that I would have shot a load if anything made contact with my dick. The holdup was my friend didn’t know what condom to buy. I didn’t know if he was a virgin. Never had that conversation with him. But he asked me to help him make a purchase. To which I responded, “hell no, man, you’re on your own!”

I’m not about to help another dude buy condoms. What was I supposed to do? Ask him to whip out his cock right there in the store? So I walked away and headed for the car. Everyone followed shortly after. My date hopped into my car, his date hopped into my friends car. Since we were quite far from either of our houses, we decided we would just find a secluded area and fuck our ladies. There was a gravel road nearby that we found. He pulled his car about 200 feet away from mine. I was too tired for sex, but I was still horny. So all I wanted was a good blowjob. I ended up getting perhaps the best head I’ve ever received. Who says drunk chicks can’t suck a mean dick?

I’m not about to help another dude buy condoms

I’m not about to help another dude buy condoms

Both women live together. So we left my car at the gravel road and got back in his car to take them home together. After dropping them off, Samir and I shared with each other what we did in the car. I told him all I got was a BJ because that’s all I wanted. He said that he fucked his woman. I high-fived him like any proud friend would do. But then he said something that was a bit disturbing…

“I didn’t use a condom”. Say what? He didn’t wrap up with a woman he had just met. For all he knows she could have STD’s or not even taking any birth control. He was 26 years old at the time. How can he be so stupid? And it’s not like he didn’t have the opportunity to purchase a condom. After all, we did stop at a convenient store for the sole purpose of getting rubbers. “I didn’t know what to buy. You wouldn’t help me”. Why a 26 year old male doesn’t know how to select a condom is beyond me. The next day was quite entertaining. He was freaking out that he contracted an STD or knocked her up. So he called her constantly to make sure she’s clean. She wouldn’t answer. She never spoke to him again.

Sexual experience

Sexual experience

My woman told me her friend spent most of that day making fun of my buddy for his lack of sexual experience. I wanted to get together with my date again. But because my friend was such a goofball, neither of them wanted to speak to either of us anymore. I remember the text I received – “sorry dude you should have picked a better date for my friend. Bye”. Lesson learned.