I am in my mid-forties and I have been online dating off and on for about 2½ years and dating in general for 4 years. I am a year and a half out of a relationship and in that time, I have found only one guy I was interested in but he did the vanishing act. I have probably more dates than the average woman and I just can’t seem to find a guy I want to date. I am often told I am beautiful and I look about 10 years younger than I my age. I get contacted by a fair number of guys in their 20’s and most I don’t respond to because I just feel it won’t go anywhere. Recently, however, I was contacted by a guy in his mid-twenties and I was impressed by his profile…he’s mature, intelligent, articulate and attractive. I started up a correspondence with him. I was curious. But I still feel that maybe it’s a mistake…what do I really have in common with this guy? After all, I am twenty years older than he is. 

In your opinion, what do guys in their twenties really expect and/or want when contacting an older woman?  The youngest guy I have ever been out with is 33. 

Thanks for your insight. I really enjoy reading your blog and I feel that of many so-called dating experts that you are right on!

Carla

Thanks, Coug–, uh Carla. As a so-called dating expert, I really appreciate the kind words!

Which is why I’m sure you’re going to be completely receptive to this:

You’re wasting your time with this kid.

Okay, that’s not fair. Let me use more words to say it:

If you’re looking for a long-term relationship, you’re most likely wasting your time with this kid. However, if you’re looking for good, clean (and not-so-clean) fun with a young stallion, you can have an amazing time. In fact, I would encourage you to do so. And take lots of pictures.

If you’re looking for a long-term relationship, you’re most likely wasting your time with this kid. However, if you’re looking for good, clean (and not-so-clean) fun with a young stallion, you can have an amazing time.

See, I’m not here to set the rules for society. I’m here to observe society and report back to you how things USUALLY work out. And for every Demi and Ashton (Celebrities, They’re Just Like Us!), there are thousands of other instances of cross-generational relationships that die a quick, painless death. Why? Because he was born in the 80’s, right about the time that you were losing your virginity in college. Because he’s been in the workforce for oh, about four years. Because he may be a great communicator, mature for his age, and relationship minded, but he’s also, y’know, a BABY.

You know how I know this? Because I’M that guy. I’ve ALWAYS loved older women. I was with a 35 year old woman when I was 20. I used to flirt with my mom’s friends. And when all my friends would make fun of me and say, “Why would you date an older woman when you could date a younger woman?”, I’d say, “Why would you date a younger woman when you can date an older woman?”. …

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I’m in my mid 30’s and she is in her early 30’s. I’ve been dating her for three months now (about 12-13 dates) and everything seems to be going well. A couple of weeks ago she asked me about my feelings, what am I feeling. Well, I told her that I like her a lot…that I’m crazy for her. She told me she feels the same way, but wants to take it slow. She mentioned that the last time she felt this sort of passion she got hurt. 

Ok, I said I understand and we can take it slow and I certainly don’t want to do anything that’s going to make you uncomfortable. I should say that we do “make out” but no intercourse. I have no problem waiting until she is ready for sex, but I would feel much better about it if we were exclusive. Neither of us have brought it up and seeing how it’s only been a few months, I don’t want push her away with the “are we exclusive” topic.

Is there something more to her statement of wanting to take it slow?

Thanks!

Brian

Dear Brian,

One of my clients had the same exact issue going on during his burgeoning relationship. He’s 22 and he’d been on about 6-7 dates without any physical intimacy or exclusivity. And although he, too, is crazy about this girl, he couldn’t help but wonder where things were going.

My instincts told me that he was a victim of “nice guy” syndrome. By being so worried that a woman won’t like him, or that he might upset her if he makes a move, he passively plays the friend card and kills all hope of attraction. I encouraged my client to not be afraid of making a move physically, and, if his date doesn’t reciprocate, sit her down for a heart to heart.

Heart to heart discussions, to me, REVEAL feelings, they don’t DICTATE feelings. Which is why having the conversation won’t change how someone feels about you – it’ll just let you know the cold, hard, truth. I wrote about this extensively for Match.com’s Happen Magazine last year. As long as you’re reasonable and not attacking, you’re just gonna get your answer by being direct. Most people are way too afraid to do this. Not my client.

Heart to heart discussions, to me, REVEAL feelings, they don’t DICTATE feelings. 

He took my advice after she declined to go “any further” than making out… Here’s the recap of their heart-to-heart in which he talked about how he needed clarity on their relationship:…

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I want to know if it is possible to have a conversation with a guy without it getting sexual? I’m not talking about a little flirting, I’m talking about body parts being described, how they would be used, etc. I’m all for a little flirting, but it seems like the internet puts no barriers on what a person will say. I mean, if I met some guy at a party, after a little flirting, he wouldn’t tell me how hard his C$(K is, now would he?!?! And he wouldn’t want to know how I think that would feel, either. Now, he may very well be thinking these things, but he would never come out and say them in person, especially after knowing me only a few minutes.

I’ve even had some quality conversations, that after a few days of talking, turn into this kind of a discussion. Is this just the way it is? Is this what I am to expect?

I don’t have a problem with a man telling me I am sexy, but if I acknowledge that, am I setting myself up for these kinds of conversations? Is there a way to avoid it, or should I just avoid these men if they go into it?

I’d love some advice on this. I’m getting a bit fed-up!

Leah

Hey Leah,

What are you wearing right now?

Sorry. Too easy.

And that’s the thing with conversations that devolve into sex talk. It’s simply too easy to go there.

This is the nature of online communications. Millions of people hiding behind their computers to connect. Except some of them are dorks parading as big shots. And some are men acting like little girls. And some are women being brazen when they’re super-shy in real life. But the one thing we know about online communications is that people can be whoever they want to be. With one amazing caveat – they’re never held accountable for their actions.

The one thing we know about online communications is that people can be whoever they want to be. With one amazing caveat – they’re never held accountable for their actions.

I want to do something revolutionary here and change that statement to “we’re never held accountable for our actions”. Because when we’re talking about policing online behavior, it always seems to imply that it’s everybody else who’s wrong, when, in fact, WE’RE what’s wrong.

No matter how you slice it, this is a societal problem from the presidency on down – we’re a bunch of hypocrites who lie and cheat and misrepresent and fabricate - and cry and complain when everyone else does the same thing. This isn’t about you, Leah. This is just something I needed to get off my chest.

Sure, I’ve gone there before – notably when discussing liars. See, it’s okay when I say I’m 5’10” instead of 5’9”, but it’s awful when a woman claims to be 130lbs when she’s really 150lbs. It’s fine when I say I have an “athletic” body instead of an average one, but it’s not cool when she says she’s 35 when she’s really 37. Telling the truth is for other people; we want the right to play fast and loose with the facts as we see fit. Because WE’RE good people. And THEY’RE bad people.

But good people steal office supplies. Good people get “creative” on their taxes. Good people write nasty things on blogs. And we do this for one main reason – because we’re never held accountable. If we were, we’d clean up our acts REAL fast….

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I’m 32, recently single and am looking forward to being back in the dating scene. I’ve tried the major online dating site in the past using a three month subscription. Anyway I noticed that online, I got few responses from men. And I don’t mean few responses from guys who match what I’m after. Just few responses in general. (Yes, my profile was visible and showed up in searches) I had my best recent clear headshot, plus a few good photos and a recent full body shot. I have what I thought was a genuine profile that highlights the things that make me stand out and I believed my words came across as witty, smart, and sincere. Not the usual “I like to go shopping, go to the gym, and hanging with friends”, yada yada yada.

Now while I was doing the online thing….I also went out to singles events after work. The strange thing is I easily met men and was asked out regularly when I went to singles events. But online it was dismal. I emailed dozens of guys with brief messages where I tried to be witty and show I read their profile in detail (like you advise!) and little resulted. I emailed younger guys, older guys, guys far away, guys nearby, skinny guys, heavier guys, etc….and never even got far enough in email exchange to get to the “talk on the phone” stage in three months. I even switched my photos periodically.

Obviously I’m sticking with the singles events because my results are much better. But I can’t help but wonder….how can I hit home runs in person yet strike out online? You’d think it happens the other way around. I also live in the NYC area, and I’ve seen many female profiles where they are “model” looking women with pictures flaunting their “assets”. Short of me putting on a sexy black dress and heels for my body shot, I’m perplexed about why this is happening. I’ve apparently got good looks and charm in person, but apparently not online. What gives?

Sara

Dear Sara,

The good things about singles events: alcohol, hanging out with friends, dressing up, excitement, music, live conversation, the possibility of “chemistry”.

The good things about online dating: inexpensive, any time of day, no need to go out, ability to market yourself and screen anonymously, ability to search, filter, and get to know people before the date, unprecedented access to members of the opposite sex all over the world.

Online dating creates far more access to singles with far more competition. Real life provides far less access to singles with far less competition.

But, as far as I’m concerned, the main difference between “real life” and online dating is this: Online dating creates far more access to singles with far more competition. Real life provides far less access to singles with far less competition.

Look around, you’ll see.

Go to a bar and there may be three cute guys in the entire place. Go online and you’ll probably find dozens within twenty miles of your home. And for the same cost as a night out on the town, on Match.com you can conceivably talk to ALL of these guys to see who is the right fit. Is it any surprise that people choose to take the online route?

But the better way for you to see the difference between online dating and offline dating is through the eyes of a man. For the sake of this exercise, let’s call this man “Evan”….

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I got an email from my sister the other day. She was forwarding an article written by Lori Gottlieb for The Atlantic, called “Marry Him – The Case for Settling for Mr. Good Enough”. Actually, that’s not quite right. In fact, she was forwarding me a link to a gossip site called Jezebel, which was ripping the author for even posing the notion that settling was a reasonable idea. So first I read the criticism, then I read the article, then I read a post-article interview with Gottlieb, and then I watched Gottlieb defend herself on The Today Show.

It was very clear that Gottlieb was onto a hot-button issue. But why was she getting attacked from all angles? Why the seething vitriol at a single mother who suggests that it might be wiser to compromise at age 34 than to continue searching through a thinning talent pool at age 40? It was clear to me that the messenger was being shot for carrying a controversial message. But it wasn’t fully clear why. So I started talking with the very people who were upset about this piece – single women, 35-45. My clients.

They told me that the piece was offensive.

They told me that it speaks more about the author than it does of them.

They told me they were very happy being single and would sooner die alone than settle.

They told me that it’s unfair to single out women for “settling”. What about men?

Now, to be clear, I am very sympathetic to the plight of women looking for love. No, I’m not a woman, which inherently limits my understanding, but I am a dating coach who listens to the fears and complaints of women every single day. You’d be hard pressed to find a man more attuned to the frustrations of single women than I am. Yet from a coldly logical standpoint, I found Gottlieb’s argument virtually unassailable.

She didn’t say settling was ideal. She wasn’t saying that you should "settle" to the point that you’re miserable. She wasn’t saying that you couldn’t possibly be happy alone. She even admits that “talking about settling in a positive light makes people profoundly uncomfortable”. So what was she saying? To paraphrase:

If you DO want that traditional American dream of husband + house + kids who look like you, then your odds of achieving it are greater if you “settle” in your early 30’s.

If you want to have your own biological children with a quality man, your options are considerably greater when you’re 32 than when you’re 42. And if that’s the case, it might behoove you to settle for a “good” guy when you’re younger, rather than hold out for an ideal guy when there are fewer quality options available.

I’m not sure what there is to argue with. I mean, you can make the argument that you’re perfectly happy being single. Great. Stay single. You can make the argument that you’d be suicidal if you were to marry the “wrong” guy. Certainly, you shouldn’t marry under those circumstances. But if you DO want that traditional American dream of husband + house + kids who look like you, then your odds of achieving it are greater if you “settle” in your early 30’s.

Here’s why:…

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I’m 24, and I’ve always seemed to have good luck with online dating.  I’ve met lots of people that way, including my last two boyfriends and a lot of now-close friends. Lately, though, I have this weird dry spell: I still get contacted, but can’t seem to make it to a first date.

I know that you recommend that people use really great, perhaps professionally done, photos. So I’m thinking of upgrading mine to get out of this dry spell. However, I have one worry about getting better photos: If I dress up really nicely, get my hair done, and get photographed in flattering lighting, won’t I look different in my photos than I will on a first date?  After all, a first Internet date is generally a casual daytime meetup, so I wouldn’t be sporting a nice hairstyle or tons of makeup, nor would I be posing under rosy, forgiving lights.

As much as I’d like to attract more men, I don’t want to do so disingenuously, because then I’m sure they wouldn’t call after the first date anyway.

I’ve browsed other women’s profiles (to check out the competition) and a lot of them use casual photos too, so I think this is a concern that a lot of women have.  Please advise us!

Sarah

I’m really quite interested in trying to figure out why you’re going through a dry spell, but that wasn’t your primary question. Let’s just save that for a rainy day.

Anyway, here’s my theory on professional photography:

Due to the enormous competition, you want to maximize your chance of getting a first date. This doesn’t mean posting a photo from five years and twenty pounds ago. But if it means getting a clear, digital, close-up of you smiling with your hair and makeup done just right, I wholeheartedly endorse it.

If it means getting a clear, digital, close-up of you smiling with your hair and makeup done just right, I wholeheartedly endorse it.

You might be more comfortable wearing sweatpants at home, but that doesn’t mean you wear it to a job interview. Your job is to GET the job. And nothing gives you a better chance to get a first date than an amazing photo of you at your BEST.

That said, I’ve always held onto this one photography maxim in regards to online dating profiles:

You’re only as attractive as your worst photo.

Which is why it baffles me that people take professional headshots and then put up a few god-awful mug shots drunkenly taken on a webcam. Anyone who clicks through is going to assume that you look like the drunkard, not the professional.

So if you’re going to go the professional route – and I encourage you to – make sure you also have a bunch of real-life digital photographs that have context. You and your friends at the beach. You and your family at a wedding. You and your dog at the park. That kind of stuff, which reveals a personality that pro shots tend to obscure….

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I am 39 and have been actively dating men in my age range. I am a single mom working 2 jobs and have 2 young kids. I don’t have a ton of time to date, but I like to have a person in my life to hang out with when I do get the chance. I tend to have 3-6 month relationships regularly.

I seem to attract a lot of men, and those that I actually date, say they were drawn to my confidence and my self reliance (of course the "hot body" is always mentioned too). Recently however, I have dated a few guys who said that I was "too emotional". If I let my guard down and expressed myself regarding our relationship, or my bad day at work, or how my confidence was flagging, it was seen as a bad thing.

Do I hide my "real" self and only show guys what I know they want to see: unyielding confidence, no negativity, no neediness? Isn’t that fake? Showing that I am human and not an ice princess is part of the "getting to know you better" phase after the first 3 months. So why am I being made to feel wrong when I do step outside of my wall and try to show really what’s going on in my head?

Rikki

Aw Rikki. I JUST answered a similar question recently, but felt there was a lot more to say. Truthfully, the real reason I chose to tackle your query was because of this one line: “Recently however, I have dated a few guys who said that I was ‘too emotional’.”

I’m not sure how you got this feedback, but such constructive criticism is INVALUABLE for a single person looking for answers. How else can we ever learn if we don’t know how we’re coming across to others? Yet most of us who get rejected prefer to assign blame to our dates, as if they were wrong for not wanting to see us again. Of course, there’s not always a reason. Sometimes there’s no chemistry. Sometimes there’s mutually awkward conversation. And in those instances, there’s nothing to learn. But if you’re seeing a pattern – “a few guys who said I was too emotional” – you’d be silly not to look a little deeper.

Now, of course, I don’t know you. I don’t know how you act on a date or in a relationship. And it’s no secret whatsoever that women can be emotional. So how does this keep coming up as a red flag to so many men? How do all these different individuals come to the same exact conclusion? Not that you’re emotional, but that you’re TOO emotional.

How do all these different individuals come to the same exact conclusion? Not that you’re emotional, but that you’re TOO emotional.

Sounds to me like you may be TOO emotional. Or at least more emotional than 80% of other women, which, apparently, causes men to want to up and flee. Those are the facts that you stated, not my opinion. So it’s no different than the guy who complained that women left him because he didn’t want to have sex, or the guy who couldn’t understand why women got creeped out when he bought them flowers on the first date. All of you are just being yourselves, yet are consternated that it’s not working. Which is why my advice to you will be the same as my advice to them. Either learn to control your emotions a bit better or accept the fact that your histrionics may be driving a lot of men away.

You’re not WRONG for being emotional, and they’re not WRONG for saying they want someone less emotional. But SOMETHING has to change if you’re going to get different results from your love life. Which is why I put the onus on you, as painful and unfair as that might seem….

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I am dating a pretty cool guy who is very sweet and attentive. I like him a lot and can see us becoming a solid couple. He says he wants us to be together in the longterm too. The only thing I’m having a tough time with are his friends. He always builds them up before I meet them by saying: "You’re just gonna love so-and-so", and then when I meet the friend, they’re mildly offensive and nothing like him.

So far, almost every single one of them is kind of a prick and a player. The one he considers his closest friend is a self-proclaimed womanizer whom I’d describe as lazy and opportunistic. This friend hardly works (I think he’s a part-time telemarketer), lives beyond his means, and doesn’t mind telling bald-faced lies about himself to impress the ladies. My boyfriend shakes his head disapprovingly and acts like he just tolerates his buddy’s shenanigans, but at the same time, he’s obviously in awe of his friend’s lifestyle because I hear him complimenting his friend on his lavish purchases and hot dates.

The rest of his pals don’t get much better. One is so rude to waiters and cab drivers to the point that it’s embarrassing to be with him in public. Another seems to enjoy bringing up the sordid details about my boyfriend and his ex-girlfriends in front of me, like he wants to get a rise out of me or something. One guy makes me feel like I have to defend everything I do, as in "What would behoove you to take a trip there? Why would you invest money in that junk? Why do you listen to that crap?" Another one admits he "collects" hot women in his life almost as a hobby. And of course there’s always-loud-and-drunk guy; we can’t forget him.

My question to you is… is the company my boyfriend keeps an indicator of something wrong with him? I respect him, but I have a really hard time liking his friends, let alone respecting them. I can’t help but wonder why he doesn’t hang out with nicer guys. I admit that I feel a little threatened that they might be bad influences on him. Or that he really is like them, but is putting on a show for me until the day he reveals his true colors. I’m also worried that I’m going to have to end up grinning and bearing my way through many nights of their company.

I don’t even know how to raise my concerns to him about his friends without coming off like the bitch who’s trying to turn him against them.

I am starting to consider ending our relationship; that’s how uncomfortable I feel about his choice of friends.

Got any advice for me on this one, Evan?

Valerie

Dear Valerie,

There were two chapters that addressed this in my book, Why You’re Still Single: Things Your Friends Would Tell You If You Promised Not to Get Mad.

Sometimes your friends actually are toxic.

One was called “Boyfriends with Boy (and Girl) Friends”. The other was called “Your Friends May Be Hazardous to Your Health”, but it was cut because the publisher didn’t think that women could handle this bit of controversy: sometimes your friends actually are toxic.

Thankfully, it’s easier for women to discuss HIS terrible friends than their own. So let’s run with that for a bit….

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