Don’t Give Up Hope

I was at a conference this weekend selling my Cassie Leigh books as well as a number of other books and I ended up having a series of conversations with men who I’d say were a little lost about how to find a new love.

We didn’t get into specifics for the most part but I think most of the guys I talked to this weekend were either recently divorced or widowed, no longer in their 20’s or even their 30’s, and just trying to figure out what to do now.

Now, anyone who has read Don’t Be A Douchebag knows I can be pretty harsh for the guys who are like a bull in a china closet when it comes to online dating.  It’s not fun as a woman to get weird or disgusting emails and every man who sends those types of things deserves the verbal beating I give in that book.

But most guys who venture into the online dating world aren’t those guys.  They’re genuinely nice guys who are completely baffled about how to navigate this new bizarre world.  (As are most women, quite frankly.)

So, this post is for those guys.  The nice, well-meaning guys who don’t even know how to get started with dating.

(I’m probably going to write a short book about this pretty soon, but in the meantime I wanted this here in case any of them find their way to this blog).

So here goes:

I know it seems scary or daunting or completely impossible to find a new love.  But as long as you’re willing to keep trying, you will find someone.

Most of us don’t find someone because the journey to that happy relationship is rough.  VERY rough.  And so we quit before we get there.

There are genuinely horrible or scary people out there, but mostly it’s just too many awkward and unpleasant dates where you wonder what’s wrong with you or with the rest of the world.  It’s like you’re trying to put together a puzzle and none of the pieces fit.

All I can say is that the people who push through that and keep trying do eventually find the right person for them.  I’ve seen it happen over and over again.  Some luck out right away and for some it takes a decade or more.  But keep trying and it will happen.

It doesn’t matter what you do for a living, what you look like, how healthy you are, how intelligent you are, or funny you are (or aren’t).  There is someone out there for you.  And if you keep trying and stay open to meeting that person,  you will find them.

Now, you may be wondering, how the hell do I get out there in the first place?

My advice?  Do the things you love and try to find ways to make them social.  If you like to cook, take cooking classes.  If you like to read, join a book group.  If you like to hike, join a group that meets up for hikes.

By doing so you are creating opportunities for that person to come into your life.

And if you can find someone who shares your interests and passions, life will be that much easier.

Plus, and this is a big one, meeting someone through a shared passion is far less intimidating and potentially disappointing than going on a date with a stranger.  You already have a shared interest, you already have an activity to do, and you can let a relationship develop naturally.

Also, let your friends and family know you’re looking.  Let them set you up.  You never know whose co-worker or third cousin might be perfect for you.

If all of that fails, sure, try online dating.  And don’t let it get you down when it doesn’t seem to be going well.  Expect failure, but hope for success.

I have a friend who is a good guy, a great catch.  Last time he tried online dating he just wasn’t getting responses.  He kept going, though, and finally met a woman he’s been happily dating for almost a year now.  Because he didn’t give up.  When things weren’t working, he looked at what he was doing, changed it  up, and tried again.

You have to push through the disappointments and keep trying.

And, yes, there will be women who ignore you.  Or say you’re not their type.

That’s okay.  It happens.  Move on and keep trying.

(And, honestly, I do think meeting people socially is the best approach for many, many people.  So don’t get stuck behind a computer sending messages into nowhere.  Not if it’s  not working for you.)

And, please, if you do try online dating, don’t let some woman convince you to send her money.  For any reason.  Don’t do it.  If you want to be scammed by someone, at least make them do it in person…

I can honestly say for each of the gentlemen I talked to this weekend, there is someone out there for you.  I know it’s hard and confusing and crazy.  But I also know you can do it.  You’ll make mistakes, but that’s okay.

Just keep going…

A Tongue-In-Cheek Guide To Moving From Lonely Singledom to Happy Coupledom

I’ve noticed that many of my friends seem to follow a pretty standard and predictable path from lonely singledom to happy coupledom.  It’s gotten to the point that I read their latest Facebook post and think, “Yep, next step is…” or, “Oops, this one’s not gonna last.”

Now, granted, what I’m about to list out says A LOT about the type of people I know and am friends with.  I’m in my late 30’s at this point and went to some pretty good schools, so the people I know are doing well enough financially to take foreign trips and buy homes, for example.  I don’t expect this list applies to everyone.  But it certainly does seem to happen far too often for me to ignore at this point.

So, what are the steps that my friends seem to follow?


  1. Get a pet.  Usually a cat.  Sometimes a dog.
  2. Post a lot of cute photos of said pet and dote on it a bit like you would a child.  FB posts about the pet should be at least 10% of all posts made, but probably closer to 50% or more.
  3. Go on a diet/get in shape.  (An optional step that doesn’t apply to those who are already in shape.)
  4. Buy a home/apartment.  (Also an optional step, but happens often enough to be noticeable.  For those who don’t buy a place, they do move into a home/apartment by themselves and spend some money/effort making it their space.


  1. Meet someone.  Often not the someone you would expect them to meet.
  2. Engage in ten times more dinners and outings than before, many of which will be fancy or special in some way.  (Think lobster and steak at a nice restaurant instead of hamburgers at the local bar.)
  3. Take long distance trip together, preferably somewhere international or gorgeous like Hawaii.
  4. Post on social media about being lucky/happy/etc. or just post photos of being lucky/happy/etc.  Gush even though you’re not the gushing type.
  5. Take second long distance trip together, preferably somewhere romantic like Italy.  (Optional step here: Get engaged.)
  6. Settle into happy coupledom.  (Not necessarily marriage, but usually something long-term like buying a home together.)
  7. Dial back on the fancy dinners and outings and settle into “real” life together.  Occasionally gush about being lucky/happy/etc. but not near as much as before.

There you have it.  Get a pet, get fit, meet someone, go out with the person lots, travel once to test the relationship, travel a second time to cement things, and you’re on your way.  Easy peasy, right?  Haha…

Compromise But Don’t Settle

I have a couple of friends who’ve been on the dating merry-go-round recently and it’s not easy.  One is a woman and she really, really wanted to meet someone so she responded to the overwhelming number of e-mails she received and went on ten to twelve dates per week until she found one.  The other is a perfectly nice, decent guy and he kept sending out message after message after message trying to meet someone.

She didn’t give up when the sheer number of men she had to wade through was almost overwhelming.  (Because a lot of the guys just weren’t what she was looking for.)  And he didn’t give up when his first messages were met with radio silence.  (Because he’s a good guy, but he was pretty generic in his presentation and approach and that isn’t going to get you much of a response in the online dating world.)

They’re both now happily in relationships.  One is even engaged.


I wonder.

Are they really both in the relationships they should be?  Or did they just get to the point where what they had was better than anything else they saw and settle for “good enough?”

Where is the line between realizing that someone isn’t perfect and settling for less than you really should?

I can tell when someone is madly in love.  You probably can, too.  I have a friend on FB right now making the most adorable comments and posts about her current boyfriend.  Those posts just scream love.  This is a woman who will either marry that guy or be with him long-term and is happy for that to happen. I’ve been friends with her on there for six years so I can SEE that she feels differently about this guy than she has any other guy in the last six years.  Another friend of mine was acting similarly a few years back and, sure enough, she just married the guy she was so over the top about.

Now, I realize that personalities differ and one person may never be the over-sharing, effusive, “I LOVE THIS PERSON” type.  I get that.  But when someone really is head over heels, there are signs.  Even little ones.  Like a smile here or a shared touch there.  There’s a sort of insular affection between two people who feel really strongly for one another.

And, with at least one of my two friends, I’m just not seeing that.

Which may be okay.  Maybe when you get to a certain age you stop trying for that type of love.  You just want someone you can go out with on Friday night and have brunch with on Sunday.  (Although I will say both of the women who were head-over-heels?  One is probably 42 right now, the other was 38 when she met her now husband.)  Maybe companionship is enough.

And that’s fine.

One of my friends and I talked a bit about this idea that no one is perfect and you have to accept that the person you’re with isn’t going to be everything you want.  And I agree.  I’ve fallen for guys over the years that weren’t everything I wanted and I was happy to let a few things slide for what they did have that I wanted.

(Hell, one guy I really liked didn’t even know how to play pool!  Hard to comprehend, I know, but he had enough going for him otherwise that I was able to look past that…haha.)

But as much as I agree with the concept, I think that there’s a point where you’re no longer accepting that no one is perfect and are instead giving up because it’s just too hard to find a great relationship.

I always figure to each his own, right?  If my friends wake up happy with where they are and who they’re with who am I to tell them otherwise?  I just…I hate to see people taking less than they could have because I also think it has a domino effect.  Two people settle for one another that means that the two people they would’ve been much happier with are now out there without them and maybe those people settle for less and so on and so on and so on….

So I guess where I’m going with this is if you are in a relationship that isn’t everything you could possibly want (which is most of us), at least make sure that it isn’t because you’ve just kind of given up and settled.

Communication Tip: Ask A Question

One of my closest friends is someone I started out just barely knowing and we came to know each other through e-mails for the most part.  And early on I realized this friend was very good at one aspect of communicating that I’d never really thought about before, namely, asking questions.

Almost every e-mail this friend sent me included a question I needed to answer.  It meant that I almost always responded, because I was raised to be polite and you answer questions when people ask them.

Think about most real life conversations you have:

“Hey, Joe.  How are you?”

“Good, Sue.  How are you?”

“Good.  What are you up to?”

We do this naturally in face-to-face conversation–prompting the other person to participate by asking them a question.

But I find that people often fail at this in online communication.

And it can kill your chances if you’re in an online dating situation.

See, here’s a terrible secret of online dating–people will respond to you even if they aren’t particularly interested.  You may just be in the “well, he/she’s not so bad I need to shut it down” category.  But the person isn’t sitting there hoping and praying that you’ll write them back.  (More true for the men than the ladies since men initiate most of the contact so generally if a guy’s done that he had some attraction to the woman before he wrote her.)

Well, if you’re in this, “eh” category, you don’t want to give the other person any chance to walk away until you can meet them.  You need to keep the conversation going.  And the way to do that is to (a) ask questions so the person feels compelled to respond to you and (b) don’t say anything so offensive or over the top that you drive them away.

I had a match fall down on this just this week.  He wrote and asked a few questions, I wrote back and answered and asked two questions, he answered the two questions.  And…I read his answers.  Neither of which made me feel especially motivated to continue the conversation.  Now, if we were in person, I would’ve followed up because awkward silences are painful.

But online?  Not so much.  It’s been a busy week and he was in that “eh” category and even if I’d continued the conversation I suspected it wasn’t going to be that interesting.

I want there to be a back and forth flow with a guy I’m interested in.  A give and take.  (Think about this for a second–it’s not just in e-mails where this matters, right?  There are other vital parts of a relationship that require working together to create a mutually enjoyable experience…If someone can’t do that at a basic level that doesn’t bode well for more sensitive areas of the relationship.)

So.  Ask questions every time you respond.  Play on the other person’s sense of politeness until you can meet in real life and captivate them with your charm and wit or sheer physical attractiveness.  (And if you’re really bad at written communication, get to that point as soon as you can.  Short responses that don’t build a conversation will do you no favors in the world of online dating.)

Dating: Sometimes It Has Nothing To Do With You

I think most of us when we approach someone we like and get turned down assume that there must be something wrong with us.  Maybe we shouldn’t have made that joke.  Or maybe our profile photo is awful.  Or they noticed our [insert physical insecurity here].

But often that’s not the case.

I closed down a match today because the guy said he can’t live without his cat.  That’s admirable.  He has another living being in his life that he cares a great deal for.  But, since I (a) am allergic to cats and (b) can’t really stand them at all, he wasn’t the guy for me.  It was nothing personal.

Unfortunately, you can’t say that on most dating sites.  You just ignore the communication or shut down the match without providing any feedback.  So, this guy is probably thinking it had to do with his age or his hairline or his taste in movies.  It didn’t.  He just wasn’t the right fit for me.

For anyone out there dating, I think it’s important to keep that in mind and not take it personal.

I had a friend just break up with a guy she’d been dating for a few months because their ideas of the appropriate amount of time to spend together were just too far apart to work.  She wanted one weekend day to herself, he thought showing up after work on Friday and not leaving until Monday morning was the way to go.  He’ll make a great husband for someone, just not my friend.

I almost shut down another match because he looks very much like someone I went to high school with.  I’m hoping he isn’t, but it was a real enough possibility that I wondered for a minute whether to keep that one going.  That had nothing to do with the guy (assuming he isn’t the guy I went to high school with).  He could’ve been perfect and if I’d decided he was who I thought he might be, I would’ve shut it down anyway.

All you need to know when someone stops communicating or doesn’t call back for that next date or otherwise doesn’t return your interest is that they weren’t the one for you.  Move on to the next person.  Because somewhere out there is the one for you.  You just have to keep going until you find them and you can’t let yourself get discouraged just because you found the wrong matches first.

(And, no, I would not recommend changing things about yourself to try to find someone.  If you want to change, fine.  If you do it out of insecurity about how others perceive you, that is not a good thing.  It will bite you in the ass someday.)

(Having said that, if you’re getting lots of rejection do have someone take a look at your profile photos.  It may just be an issue of how you’re presenting yourself.  Try to put your best foot forward.)

Why I Unfriend People on Facebook

I’ll admit it, I’m an unfriender.  While everyone else is connecting to their third cousin’s friend from Sunday school, I’m busy culling my list of FB friends.  I wasn’t always like that.  When I first joined the site I pretty much accepted a friend request from anyone I’d ever met–even one of my professors.

But then time passed and I watched how things worked and decided that I didn’t really care about how many friends I had on FB.  I cared more that my friends on FB were friends I wanted.  (Much like middle school…)  Now, interestingly enough, some of the people I didn’t think would last have and some of the ones I never thought I’d unfriend have gone by the wayside.

So, what are my top reasons for unfriending someone on FB?

1. They never post.  Anything.  Ever.  The only time the person shows up in my newsfeed is when some random person I don’t know tags them in a post with pictures of other people I don’t know, usually their children.  I think it’s great that FB can be used to keep someone up to date on what’s happening with their friends’ kids, but I don’t care about those nameless children, so if there’s not some other reason to stay friends with the person, I”m eventually going to unfriend them.

2. They post all the time about things I don’t care about.  I appreciate that people have political and social views that they want to share with others, but after the twentieth post in a week about, well, any political topic, I’m done.  Sometimes I’ll just hide the person from my newsfeed for a while to see if it blows over, but generally it doesn’t.

3. They post passive-aggressive drama posts often and I’m allowed to unfriend them.  (I have one that I can’t.)  You know what I’m talking about: “I hate when mean people are mean.” or “Well, at least I now know who my true friends are.”  If you can’t keep your drama between you and the people you have drama with, then we don’t need to be friends.

4. I can’t remember who they are.  Or, more likely, I remember that they’re that person I met that one time at that party and have never exchanged another message with.  I don’t like their posts.  They don’t like mine.  We are as much strangers on FB as we are off of it.

5. They’re on FB all the time but we never interact.  I see new posts by them, but none ever inspire me to comment or like them.  They never comment on my posts or like them either.  I know this person.  We went to college together or worked together for years, but I don’t know why I’m still in touch with them.

6. I’m not positive I actually know who this person is.  They have the name of someone I used to know and they sent me a friend request, but they’ve never posted anything that actually confirms they are who they say they are.

7.  It’s complicated and I finally figured out the way to uncomplicate the situation is to unfriend them.

8. They post mocking or  hateful posts often and I’m allowed to unfriend them.  (I have one I can’t.  Interestingly enough, not the same person as in 3.)  I don’t have much patience for people who hate other groups of people or who feel superior enough to mock a whole group of individuals.  I’m not above the occasional insult myself, but I try to limit my negativity to people I actually know.

9. They’re going through some serious personal drama that they’re talking about on FB and I don’t know them well enough to provide emotional support and I feel like a vulture continuing to watch the train wreck which is their life right now.

10. They are more appropriately a LinkedIn-type contact.  This includes former co-workers I don’t socialize with as well as former professors and classmates I never socialized with.  They don’t need to see my posts about my dog or the latest song lyric I liked.  They just need to know where to find me and what I’m up to professionally.

There are a few other one offs, but that covers the majority.  I have to say, it certainly makes being on FB a much more enjoyable experience than when I had all those other folks on there.

If You Love Someone, Disappoint Them

Most of us when we meet someone we really like do everything we can for them.  We’re on time for dates, we ignore work calls while we’re with them, we agree to go out for African food instead of suggesting a good old cheeseburger, we watch that independent black and white film instead of the latest blockbuster…

Well, okay.  Scratch those last two.  At least if you’re me.

But most of us do try to accommodate the ones we love (or like).

Problem is, sometimes the other person is in it for different reasons than we are.  We’re busy falling in love while they’ve just found someone accommodating so figure why the hell not go along with it.

See, as long as you’re making someone’s life easy and doing everything they want, it’s not too hard for them to put up with you.  You only really find out how someone feels about you when you say “no” or don’t give them what they want.

So I say disappoint them.  Let them down.  Say no every once in a while.

If they really care for you, they’ll recover from it.  They might take a moment, but as long as it’s a one-off occurrence they’ll work through it and accept the fact that you can’t be what they want you to be 100% of the time.

If they’re just in it for what they can get out of you, they’ll throw a little hissy fit or walk away.

That’s okay.  Let ’em go.  Because if they can’t handle a little compromise every once in a while they really weren’t the one for you.


Sunk Costs

If you want a good laugh, you should really listen to this.  It was on the radio the other day.  One of those bits where they call a guy up and offer to send roses for free on his behalf to see if he’ll send them to his girlfriend or the woman she suspects he’s cheating with.

(Note to men: Why do you still fall for this crap?  I’ve heard these types of shows in at least four or five radio markets, so it’s not exactly new.  If you’re cheating and a stranger calls you up and offers to send a woman free flowers on your behalf, say no.  Or send them to your mother.)

Anyway, this one is funny because it turns out the woman is absolutely crazy.  It’s worth listening to for that alone.

Somehow this woman failed to comprehend that it’s not okay to break into a guy’s house after he dumps you and leave him a note about how you can get to him anywhere.  And that it’s also not okay to then call a radio show to see if he’s “cheating” on you two months after he dumped you.

But that’s not why I’m linking to it here.  I’m linking to it because this woman’s rant reminded me about the concept of sunk costs.

Basically, it’s the idea that people make bad choices because they think about what they’ve already invested in a situation rather than looking at it as a new choice each time.In money terms:  Say you’d paid $500 to fix your car and now you’re told that it will cost another $500 to fix it.  You may be more likely to spend that $500 to fix it rather than selling the car and walking away because of what you’ve already spent on the car.  It’s not logical, but people do it all the time.  That first $500 is gone.  It’s spent.  Nothing you do now will get it back.  But, because you spent it you’re tempted to stick with the car and keep trying.

Well, let’s bring it back to relationships.  The woman on this call is talking about a guy who is supposedly cheating on her and has done so in the past and she explains why she’s staying with him by saying, “…he met my friends, he got the friends’ seal of approval, he’s been over to my house…I’ve let him meet my parents…”

She was focused on the wrong things.  On what had come before.  On all the time she’d spent on building this relationship.  She couldn’t let go of it.How could she possibly walk away from a guy who was cheating on her when she’d invested so much into the relationship already?  She’d put herself out there.  Let him meet her friends.  Let him meet her family.  Told him she loved him.  (An honor heretofore reserved for her dad and Jesus.)Problem with that approach to dating is that you can “but I’ve already…” your way right into a really shitty marriage.

Happened to a friend.  She knew she shouldn’t marry the guy.  But the wedding hall was booked and the guests were invited and everyone knew she was getting married.  So, against every instinct in her body, she married a drug-addicted abusive asshole.

Don’t do that.  If your gut is screaming at you that something is wrong in a relationship stop thinking about sunk costs.  Stop thinking about “but I’ve been with him for five years” or “but we have a house together” or “but we have kids together.”

Those things matter, but not in that way.  Not in an “if I stick with this a little longer it will finally be what I want it to be” sort of way.  They matter in the “we’ve built something together and have a special, shared connection unique to us” sort of way.

Does that make sense?

Don’t hang in there just because you’ve spent so much time and energy on it.  Hang in there because it’s worth hanging in there for.


There’s something to be said for persistence

I was reading this article the other day about Mickey Rooney’s many marriages.  Turns out the man was married eight times!


But the reason I’m writing about it is because that last marriage lasted thirty-four years.


(Seems I’m repeating things a lot today.)

Now, he could’ve had that first failed marriage to Ava Gardner and said, “That’s it.  Relationships are just too hard.”

Or maybe after the fifth one when his soon-to-be-ex wife’s new boyfriend killed her.

But no.  He kept trying again and again and again.

Now, one could argue that maybe he could’ve skipped all the trips down the aisle, but I think that was more how things worked at that time.

My own grandma was married some ridiculous number of times.  She did the same thing as Rooney, though—kept trying until she got it right.  And her last marriage lasted fifteen plus years until she passed away.  So, she, too, found happiness in the end by continually being willing to try and try again.

I thoroughly believe in the million monkeys theory of dating.  (I just made that shit up.)  Basically, the idea is that if you keep trying, keep getting into relationships, eventually one will last.  Try enough times, one will work. (Just like if you put a million monkeys in front of typewriters, one will eventually manage to write something decent.)

Think of all the trainwreck people you know who spin from insane relationship situation to insane relationship situation.

I knew a girl who dated and married a co-worker, then dated her boss, then dated a partner at her law firm, and then finally ended up happily married to a former co-worker.  Now, some folks might have hesitated to go there.  (I would on all four counts.)  But, she made it happen by being willing to take the risk.

One thing is certain: You sit on the sidelines you don’t get anywhere.

I have another friend who just started online dating and has been on twenty dates in three weeks.  And the twentieth date is looking pretty promising.  Now, she could’ve given up when getting those twenty dates meant wading through a hundred plus inane e-mails.  Or she could’ve stopped after that first awkward as hell date.  Or the tenth.

But she didn’t.  She kept trying.

She didn’t settle.  You can’t settle.

But she didn’t quit trying either.

So, if you really want it, keep going.  It’ll suck sometimes.  But try enough, and someone just might stick.