3 mistakes to avoid if you’re dating again

by singlemomseeking on September 11, 2010

1. Don’t fib

You don’t have to spill every personal details about yourself — or about your kids — on the first date, but be yourself. Examples: If you’re separated, but not yet legally divorced, say so. If you’re 42 years old, don’t say that you’re 39. You get the gist.

2. Take it slowly

Chemistry really does do magic, especially if it has been a LONG time since… you know. On a first date, if you’re really clicking, maybe you can savor that long hug and/or kiss at the end of the night — and then take a deep breath and go home alone as you savor your amazing night. Imagine what you’ll have to look forward to next time!

3. Keep your kids out of it. For now.

Introducing Mr. Could Be to your kid is not cool. If you’re a solo mom — without a co-parent — this can be tricky. That’s where good friends come in to trade babysitting, or family if they’re nearby.

If you had a miserable date, tell your girlfriends all about it — not your kid. Of course, the time and place will come when you feel ready to introduce your boyfriend to your child. But what’s the rush?

Tell me:

Are you dating again?

If so, how’s it going?

If you’re not ready yet, what’s holding you back?

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{ 31 comments… read them below or add one }

Shevy September 29, 2015 at 12:09 am

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2-Brides September 20, 2015 at 4:10 pm

Taking it slow is the hardest thing for me. What is it with that? Sometimes it can be very frustrating but I like what has been said here..not compromising my values is what I have to remember. Thanks for this post.


Lisa Kurnia March 5, 2015 at 7:29 pm

I am a 42 year old womn of 15 year divorce. I have got a teenager daughter who is more bff than a daughter. I am seeing my online date man for the first time. Tomorrow! I am so nervous. Thousand of ‘what if’ questions flooded my head. Really need huge help here.


Tracey November 6, 2011 at 7:47 am

I’m a dating coach and I really enjoyed reading everyone’s comments on dating mistakes to avoid. Thanks for sharing them and an even bigger thanks to you for sharing your own thoughts. I think your advice is great and I agree with so much of what you write. Keep up the great work!


BigLittleWolf September 24, 2009 at 11:15 am

Late to this party, but… I have a word for Legal Editor Mom, another word for Caryn, and a question for you, Rachel…

L.E.M. – you said something about being “too” picky. I frequently read your comments and nod in agreement, but as a (presumed) wordsmith – beware words like “just,” “only,” and “too” when referring to yourself – your needs, your capabilities, your ANYTHING. It’s something that we (women) do so often, and it’s more than just semantics. We ever diminish ourselves and our knowledge of self with these words.

I doubt you are being “too picky.” I strongly suspect you know what you like and need – and while your criteria may be discerning and different from others you know – it’s your (necessary) criteria. Nothing “too” about it. (Now if you said the man you’d like to find must have three freckles on both cheeks like your 3rd grade boyfriend, I might say that’s too picky…)

Caryn – I’ve got 20 years on you, and I still feel “clueless” – after many years dating (on two continents), many years married, and now 8 years single again. At the same time, a feeling is not equal to “reality.” I think if you talked to many men as well as women, they are as befuddled by how to find people with whom they might click, and befuddled is probably closer to an accurate term than “clueless.”

One more thought – there is no “properly” or “improperly” to meeting people, dating, loving, or any other sort of relationship. There are only an infinite number of ways for it to happen – with all kinds of possible results. I’ve found friendship, love, hook-ups, work, and “angel moments” on the internet, in my local coffee shop, on a commuter train 600 miles away, in an airport (twice!)e , and who knows where the next wonderful moment might come from.

You’re 30. There’s so much ahead. And it will happen!

Last (apologies for length of comment) – Rachel – whatever happened to 40-year old “Rita,” the single mom in the Pacific Northwest who was with a “sweet man” who was ho-hum in bed and unwilling to change? Do you have an update? 40 (to me) is young and vibrant, and I’d like to think that she’s not compromising fundamental parts of who she is, thinking she can’t do better.

No guarantees for any of us. But without risk, we get nowhere.
.-= BigLittleWolf´s last blog ..Sex OK in the Sooner State? =-.


Caryn September 23, 2009 at 11:26 pm

I have done online dating since my divorce 3 years ago because as a single mom, I don’t get out much. I have met a few different men and recently ended a 9 month relationship with a guy I met online. The problem is that I’ve never met or dated anyone I have ever originally met in person. I married my first boyfriend and just recently had my second boyfriend. At 30 I am clueless about how to do this properly…I need the help!!


MC September 15, 2009 at 5:45 pm

Thanks, Priscilla! And good luck with Opera Guy!

Guess I need to look for a psychic around here…maybe they could tell me what’s going to happen with my “Mr Married”. I’d know I should avoid him as a bad prospect, but honestly he looks just like Patrick Swayze, except ‘way taller and with a beard. And he can’t dance (I asked him–the look of panic in his eyes was just hilarious! Typical guy.). RIP, Patrick.


MC September 13, 2009 at 8:30 am

OK, that was too long–sorry.

The short version is: I’m finally over my divorce from my marriage to a controlling jerk, my kids are almost teenagers and getting more independent by the day, and my life seems to be expanding outward. I want to find someone to enjoy with me all that life has to offer! I want a man whose approach to life is characterized by poetry, courage, and wisdom.

But all I can find are men whose vision of the future is all about things closing in and getting more limited. I don’t want to deal with anyone who has a negative/bitter world view, or raise several small children (OMG, not again), or nurse further into decline a man who is much older than me and who sees his life as essentially over.


Priscilla San Remo September 13, 2009 at 12:33 pm

Hang in there, MC! That was me not too long ago. Once my son neared HS graduation, I started exploring distance online dating, as I also live in a small Midwestern town (it thinks it’s a city–that’s another story!). I had a few true distance dates and a lot of dates with men who live within a three-hour drive (the nearest big city where I wanted to spend time). I had a large volume of email and phone correspondence with guys before I would meet any in person–I’m not too picky about age or looks, but intellect and engagement with life have to be there.

Ironically, this spring, after I had just sworn off any further contact with an on-again-off-again long distance guy, I got an email from a university professor who lives, it turns out, in my neighborhood. A psychic (yeah, I do a reading every spring, and she’s right on the money) had been telling me for two years that there was a “professor right in my back yard” that I should meet, but I was so focused on getting out of the midwest, I wasn’t even looking in my home town any more!

Needless to say the professor, AKA Opera Guy, and I have been virtually inseparable since then and match up in ways I couldn’t have imagined. We have great conversations together and our levels of physical activity match up nicely. Our kids are even one year apart and knew each other in school.

Prior to meeting Opera Guy, I had met so many men who weren’t right for me. I was nearing the end of my dating rope, so to speak, this spring when I picked up Patti Stanger’s book “Become Your Own Matchmaker.” Most of the book wasn’t groundbreaking, but the chapter on “Dating Detox” did it for me. I went a month without any dating or online dating activity and focused on myself and my needs. The book even suggests giving yourself a little makeover, if you want to change something about your physical appearance or give yourself some rejuvenation.

No guarantees about my future with Opera Guy, but things look promising so far. Good luck.

P.S. Rachel, sorry for yet another long comment 🙂


singlemomseeking September 15, 2009 at 11:03 am

Priscilla: Keep the long comments coming! I love hearing your stories. That goes for all of you.

I love the fact that a psychic knew there was a professor in your backyard, just waiting for you. Wow.

MC September 13, 2009 at 6:03 am

I’m in late forties, and dating for me has really been a trial. Apparently there just aren’t very men out there in my age group. Particularly since I live in a smallish town in the Midwest.

The men my age or younger seem insecure about their careers/finances (I’m secure in both, which freaks them out) and are looking for either 20-something women or “moms” for their 4+ young children (I have 2 of my own–children are fine but no way would I take on 4 more!). But the older men now seem REALLY old and I don’t find them attractive.

I’ve done a lot of online dating and also used two dating services; I’ve also dated men who work at the same company as me (although in different departments). I’ve been married & divorced twice and I’m not looking to get married again necessarily. But I would like a long term partner, to live with and continue the adventure of life together.

Currently, I’m dating a man from work who I’m crazy about, but I’m not optimistic about the relationship going anywhere. He’s near my age (yay!) and been separated for 2 yrs, but he’s not divorced and hasn’t even filed yet and I had to flirt outrageously to even get him to ask me out. I know he’s a bad bet, but it’s sooo nice to be with a man who is otherwise pretty close to what I’m looking for.

The age problem is strange for me–before my last marriage I primarily older men–but now these “older men” are in their 60’s and they seem very old. They talk about retiring in a couple of years (!), they seem to be “done” in terms of engaging with life, they worry about their prostates (!), and they can’t keep up with me physically (they’ve given up downhill skiing and jogging, they need a nap in the afternoons, sex is…underwhelming). Not that I’m an athlete, mind you, but I don’t want to get together with a man for whom it’s all downhill from here on out. And I worry, what about 10 years into the future? I’ll be newly retired, and he’ll be… dead?

I’ve found that online is way better–you can email and flirt and check chemistry (& spelling!) even before you meet. If I meet a man online and he can’t even compose a coherent and clever email—no way are we getting together. I agree with Mike posting above–people online just get out more. The dating services on the other hand seemed to select for men with zero social skills–I’ve met 15 guys so far and I consented to go on a 2nd date with only one (& that was a mistake!). Although about half the men have wanted a 2nd date. You know it’s bad when you can’t make it through dinner with a man without feeling like you are, personally and all alone, hauling uphill the huge heavy boulder of small talk! And so many of them seemed to be bitter right-wingers and/or super religious in a weird and off-putting way.

Probably I should just move somewhere else! But any advice would be welcome.


singlemomseeking September 13, 2009 at 9:50 am

@MC: I love long comments. I feel like I’m listening to you over coffee. Thanks.

You sound so grounded. And, wow, you could move somewhere else after your kids go to college, couldn’t you? Oh, the possibilities!

You cracked me up with your description of, uh, older men….


Anna September 12, 2009 at 6:05 pm

I’m on a hiatus, and not sure when/if I will actively seek a date again. I tried the online thing, and just wasn’t impressed. I’ve dated 2 guys in the last year, and one of them for only 2 dates. I feel like a lot of money was wasted because many users have set the bar incredibly high, as if plugging in their “must haves” will then cause the computer to spit out their ideal mate. The whole experience didn’t do much for my self-esteem, either. I’ve heard that people have much better luck with being introduced to friends of friends, anyway. Right now, I just don’t have the time or inclination to pursue a relationship of any kind.


Priscilla San Remo September 12, 2009 at 8:57 am

I’ve done online dating on and off again for the last 10 years or so. I’ve had a couple of long-term relationships through online services and am crazy about the guy I’m currently dating, whom I also met online. I’ve had a few duds, a few out-and-out crazies, and a few guys who misrepresented themselves. My theory is you have to kiss a few frogs to find a prince.

I have to say that while services that do background checks on potential mates can be helpful in uncovering things that are a matter of public record (appearance, marital status, criminal background, etc.), it starts to verge on invasion of privacy when they want to look at whether or not someone is in debt. Are the subjects of these investigations volunteering their social security numbers for credit report searches? If so, fine. If not, it could be illegal (and at least immoral).

Personally, until I start discussing cohabitation or marriage, the intricacies of my personal finances are no one else’s business. I’m always up front with anyone I’m serious about regarding the generalities of my financial life. I try to get a sense that we look at money in roughly the same way. But my FICO score, my credit history, my mortgage balance–those should not be under scrutiny by someone I haven’t even met yet!!!


singlemomseeking September 15, 2009 at 11:05 am

@Priscilla: It’s so fascinating to me that what might be a deal breaker for one person… isn’t such a big deal for another. I’d love to know if being in debt is a deal breaker for other women, too.

Of course, this isn’t information that’s easy to uncover on a first, second, or third date. And having a few thousand dollars on your credit card is not much compared to a $100,000 college debt. Anyone else want to chime in on this one? Thanks!


susan July 26, 2011 at 5:22 pm

It sounds so shallow to say that money is an important factor/deal breaker but truthfully, yes it is.
I am not so worried about asset base but I am extremely nervous of the guy who ‘had it all’and lost it all. I mean, how does someone get to mid 40’s and still have nothing, or worse, have Ăşnhealthy’debt and little else. To me it suggests other things, like an inability to budget.
Even more fascinating is how many of these guys still have great cars, the biggest TV i’ve ever seen, PS#’s, ipods, iphones, and expensive hobbies.

OaklandMama September 12, 2009 at 12:58 am

Aghh! Online dating is a nightmare! I’ve tried (and failed) for several months to find even one dating possibility. I think I’d rather introduce myself to strangers on the street that continue down that road! Would love some help from a pro…


from the desk of ..me September 11, 2009 at 9:27 pm

i’ve been dating the same guy for almost a year and things are going well. we met at a karaoke bar. i have tried online dating but wasn’t successful. i found that the chemistry just wasn’t there. my current relationship is progressing well. there’s even been some talk about marriage. as a 30 something single mom who has never been married, it’s hard to not fantasize about the possibilities of becoming a mrs. lately, i’ve found myself enjoying the moment and finding peace in knowing that what will be, will be.
.-= from the desk of ..me´s last blog ..Day One In the Lap of Luxury =-.


CC September 11, 2009 at 8:09 pm

I too have tried many websites and I cannot seem to get past one or two dates with these guys, if they don’t fizzle out and we actaully meet. My Grandmother always tells me I need to try “3 bites” to even know if I like them, although I usually can tell after just 1 or 2 dates and the third is usually miserable. I think dating back then was a little different. Meeting in person seems like the better option but it just is not happening. I would love some dating help too!


Legal Editor Mom September 11, 2009 at 7:13 pm

I tried online dating, got no value for my $, and even the free sites were “draining” and time wasters. It’s not for me and I won’t do it anymore. I prefer to meet someone in person and KNOW what I’m getting. For the most part I believe that what Carole says is right on.

I too am picky after learning from my disastrous marriage what I DON’T want, and I absolutley will not waste time on someone I’m not compatible with, and I will never settle. I am very comfortable single and in what my daughter refers to as our “girls’ house.” I’m fiercely independent, self-sufficient, and content. That said, I do date and currently have a love “interest,” but he understands that my child comes first and my time is extremely limited. I am open to getting married again, but I’m moving at a snail’s pace towards pursuing that and will only do it if I am absolutely certain. Only time will tell if Mr. Right Now is Mr. Right. Until then, my child is my main focus and priority in my life.


Melinda Graham September 11, 2009 at 6:27 pm

I’ve been dating up a storm of first dates, but not finding a keeper – not even someone I want to see for a second date.


mg7630 September 11, 2009 at 6:09 pm

My dating life is terrible! The last guy I went out with was a single dad who was THRILLED to be single. He “only has to deal with his kids a few days a week” (his words) and then he goes out and hooks up the rest of the week. Unbelievable! Bragging about how often he hooks up! I wonder if I’ll ever find love again.


Mommy to the Monsters September 11, 2009 at 5:24 pm

Well my dating life is non -existent @ this point. I was engaged over a year ago and for many reasons that didn’t work out. I really didn’t date much prior to being engaged either. I am really picky.

I think now that I am a single mom I have become even more picky. I’m don’t have time for casual dating. I only want to date with the purpose of being married. Not saying that we will get married, but really I don’t have the time or energy to be casually dating someone who I don’t “potentially” see my self marrying. I think that it’s a waste of his and my time because it will ultimately lead no where because I refuse to settle for less than God’s best for me and my son’s. We deserve it, I won’t settle for less.

Case in point this man tried to hit on me Monday, at first glance I know he was older than the men I would usually date, but I gave him my phone # anyway, because I was like he maybe “the one”. Well after a 10 min phone conversation later that night I knew he wasn’t.

Our morals and values and spiritual beliefs are WAY different. STRIKE ONE (Really strike one was enough in itself to eliminate him)

He immediately was trying to visit my house and meet my kids. I told him I wasn’t comfortable with that just yet and he kept persisting…I was like NO WAY…STRIKE TWO

He is much older than me than I thought. We are in 2 different stages in life….. He has grown kids only a few years younger than me and a grandchild almost the same age as my youngest son. All his friends are old enough to be my parents. We have absolutely NOTHING in common. From the things we discussed I have more in common with his kids than with him. All of this might not be a negative to other people, but was STRIKE THREE for me…..

I would thoroughly enjoy if I could have a pre-screened selection of men to be matched with and then I wouldn’t have to go through now trying to explain to a perfectly nice man that there is no point in us dating, as I am NEVER going to marry you because I refuse to compromise especially on my morals, values and spiritual beliefs…
.-= Mommy to the Monsters´s last blog ..Throw Back Pics of the Boys- Memphis 2007 =-.


Lindsay December 22, 2012 at 6:38 am

Wow I relate to this so much! Absolutely do not compromise your morals and values. I am very quick to see if Im compatible or not with someone based on a few questions about spirituality and background. Since having my son, I am too very picky and do not wish I settle. My recent struggle is with a guy who is perfect for me on paper… Then we met and there was a definite spark. Dad of 3, great job, handsome, spiritually aligned with me.. But he’s not interested in having more children and I’m 29 with one and definitely want to. So what do I do??


Restless Mama September 11, 2009 at 3:29 pm

Just now interested in dating again but very skeptical of what kind of fellas are out there.


singlemomseeking September 11, 2009 at 4:33 pm

@Restless Mama: Until recently, I was just as skeptical! But that little tiny speck of hopefulness kept me open. What do you say?


onemanthreekids September 11, 2009 at 2:29 pm

Maybe this is the answer! Maybe I am the problem? Can a third party shed the light on why my luck has been so hit or miss? I have tried all the major online dating sites at one point or another. I had some good luck and I had some bad luck. The process is so draining…you never know if the woman’s profile is active, if the pictures are recent, if she is even reading what you send…. It can be draining and expensive. I tried them because my job and my kids don’t allow me to meet many new women. Let’s face it I live in suburbia and I spend time with married folks that have kids. These were chances to broaden the spectrum, create exposure.
Being a single dad with three kids (whose mother is deceased) is a challenge all by itself… then you add on whomever I date has to want to eventually step up and be Mom… Let’s just say finding the right one has been difficult and deep down I don’t want to really wait eight years until I am forty-three an my youngest decides she is too cool to be seen with me.

.-= onemanthreekids´s last blog ..Could it be? Yep…it is me. =-.


singlemomseeking September 11, 2009 at 4:34 pm

Is it REALLY you, @onemanthree kids? Oh my! You haven’t posted for a year! It’s so good to see you!

Last we heard, you were dating someone special? Do tell! Big hug.


Lisa H. September 11, 2009 at 1:48 pm

I have gone out on a few dates in the last ummm … 4 years since my divorce. I met these guys online. But I am so curious how people meet other people. No single guys at my work, joined karate, but 50% women, 40% kids. I am always looking for ideas.

Would love to win the dating help :).


Mike September 11, 2009 at 12:20 pm

Online dating was good in the beginning to get my feet wet. However what I find is that people that online date don’t go out and mingle. They’ve been absorbed by there lives which I don’t find to appealing. So meeting women were ever has been better or either finding numbers on the bathroom wall.s

So you know your pics aren’t showing.
.-= Mike´s last blog ..Good Day Sunshine =-.


Katherine SOLOdotmom September 11, 2009 at 6:57 am

Am I first this morning? Well I am presently in a relationship but I have tried online dating and dated through that route for years following my divorce prior to meeting my current Mr. M. who I also met online. So I can appreciate the idea of not wanting to waste time by having someone do some more background checking for me prior to that first date… I went through many disappointments… and even blogged about a few, lol. But since I met Mr. M. .. this one is getting more serious than any of the many many dates prior.

Anyways… so I am hoping for one of the posters.
.-= Katherine SOLOdotmom´s last blog ..Yesterday…. =-.


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