The First Date

by mssinglemama on February 8, 2009

Single mom or not, first dates can be pressure cookers.

first-dateWhen I was 12-years-old I rode my bike to my first date… my first date — ever. I had spent the entire week fantasizing about what it would be like, wondering if he would try to kiss me or tell me he wanted to take me to a party.

Funny how little I’ve changed.

It’s a girl thing, I suppose. We just want some kind of magical moment. Usually all it takes to create one of these moments is a dash of physical chemistry, a splash of attentive listening, and then a long gaze with a soft smile and an assertive phrase like, “I’d love to see you again” or “I’m so happy I met you.”

That usually gets us.

Oh, and always walk us to our door but do not invite yourself in. For the guys, here’s an article from on Successful First Dates, read the part about the difference between assertiveness and aggression.

That very first date of mine ended with a giddy bike ride home. In my mind our putt putt golf session had been amazing. I can’t even think of why. Maybe because he smiled at me a few times and actually stayed to play. I was a dork by the way. A huge dork.

He never called and because he went to a different school – the reason I got the date in the first place – I never saw him again. My next real date wouldn’t come until I was 15 and living in an entirely different state. [No pity for the dork thing please – it was good for me, gave me some back bone at an early age].

So back to Tuesday’s date … now as a woman and a single mom, dates are still just as simple but the inner dork of mine is incredibly freaked out.

Honestly, I’ve had very few “formal” dinner dates before. My first dates in the recent past have been casual bar meet-ups or group dates. So this is new territory and I’m a bit fuzzy on those pesky rules.

I did some research and aside from some really, really bad articles on first dates  I found this video on And although it’s quite freaky to hear a man talk about a first date like it’s a scientific experiment, he does make some interesting points. One of which is that guys must pick up the check, absolutely must, if they have any interest in the woman. If not, let her split it, but don’t expect to see her again. And if the woman insists on splitting, she’s not interested in anything past friendship – again, very true.

The big “no, no” in this video and everywhere else is talking about the ex. That won’t be a problem. Ancient history. But other first date experts say not to talk about your kids.  I understand that when we date the childless we can’t gush too much about the kids on the first date, but I will be talking about Benjamin – it would be impossible not to. His existence affects every aspect of my life. And he’s one of my life’s greatest achievements. I’m not going to muffle myself when it comes to my son. If he comes up, he comes up.

There’s also something the video dude calls the “rule of least interest” – whoever appears to be least interested has the upper hand. How can you fake being uninterested in someone?

If I’m interested the guy knows. I’m not going to get all crazy on his ass and send him presents or light up his phone – but I’ll make it clear that I’d like to see him again.

My conclusion? I’m just going to forget about all of the advice, the stupid rules and just be me, just like I was when I was twelve. A click is a click and if it’s not there, you can’t force it no matter how many rules you try to follow. But I’ll be taking mental notes because clearly someone needs to make a good first date video for single parents. :   )

So what are your first date pointers? Have you been on one since becoming a single mom? Any horror stories or good ones?

P.S. And no, I have no idea what I’m going to wear. But it will have to be dressy because he picked a nice restaurant.

P.P.S. Yes, I’m completely freaked that just writing about this is going to jinx the date but – to hell with it – this is good material. But God forbid he finds this blog before I can tell him about it.

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{ 33 comments… read them below or add one }

Melissa February 8, 2009 at 11:49 pm

Be yourself! If there is one thing I have learned since I started dating again is that men find it very attractive when a woman can "act" like herself.

You are charming and funny in your post, i am sure it will come out in the conversations you have while on a date.

Good luck!!!


Lesli February 9, 2009 at 1:03 am

You are going to be so fine–you already know what to do–be yourself. And I'm sorry….but if a guy is "turned off" by kid-talk, you wouldn't want that guy anyway!! I do think that's one reason I tend to only want to date single dads….people without children (male or female) just can't relate in many ways. Anyway, have fun and just roll with it….
p.s. Just returned from Target–and what is up with all the crazy-ass print/pattern shoes? I feel like I'm reliving the 80s (from my Preppy Handbook)!!


Barbara February 9, 2009 at 2:08 am

Being way too talkative can be a dead give away that you're nervous OR might give him the impression you're trying to impress him or be too amusing. I'm sure you'll do just fine.

Love your blog, and because of this i started my own πŸ™‚ you are truly inspiring and funny! Goodluck!


March Liz February 9, 2009 at 2:24 am

Oh exciting!!
I actually have a first date this week too but I am trying to think of it as a casual meeting between friends…yep, that's not working so well! It is also my first date since my daughter's father and I broke up so it will be interesting. The butterflies make it fun though right!!


March Liz February 9, 2009 at 2:26 am

PS, I have no idea what I'm going to wear either!!


Ms. Single Mama February 9, 2009 at 2:37 am



syd February 9, 2009 at 3:23 am

Go you, I love it. And I am all about just being you – it's absolutely the way to go, rules out the window. πŸ˜‰


Midwest Irish Guy February 9, 2009 at 4:01 am

Just be yourself. Be confident that you are awesome. The right guy will see that. If you have to play games to have a relationship, it's not worth it. I had to learn that the hard way. Even though I don't have a child, I have been divorced, and dating after that has felt a little weird. Don't worry – if the guy doesn't like you for who you are, just consider the weeding out process that much easier. πŸ™‚ Being a guy, I can say that REAL men respect all of you single moms. πŸ™‚ Any guy who doesn't appreciate you for who you really are isn't worth being with.


Juggle Jane February 9, 2009 at 4:03 am

I completely agree with you re: talking about the kids. If I was dating a single dad, I would find it fishy if he didn't mention his children on the first date.

My first first date as a single mom went well. It was the following dates that went downhill. πŸ˜‰


Midwest Irish Guy February 9, 2009 at 4:03 am

Oh, and don't worry about the rules…they are BS. πŸ™‚ Just have fun!


thewarriorpoets February 9, 2009 at 5:48 am

Have you ever wanted to comment on a blog, but you knew it was just going to get you into trouble… so you went back forth… should I? Nah. Maybe. Nah. But I have to say it. Just shut up, Christopher.

This is so hard to explain without monopolizing your comment section, but I'll try. Relationships require intentionality. Some people call it "rules". Some call it "strategy". Some call it "games". Call it what you will. It helps to have a loose plan, some guidelines, and a solid understanding of human behavior. Yes, sometimes it just clicks. But when it does, it's because both people's behavior fell within the spectrum of the "rules" and both naturally played their stategy, even if it was not thought out but purely based on emotions. I say, better to go in with some thought put into it.

And know when rules were made to be broken.

Ah. Felt good getting it out. But I having a feeling I may pay for it. πŸ™‚


thewarriorpoets February 9, 2009 at 5:50 am

Have you ever wanted to comment on a blog, but you knew it was just going to get you into trouble… so you went back and forth… should I? Nah. Maybe. Nah. But I have to say it. Just shut up, Christopher.

This is so hard to explain without monopolizing your comment section, but I'll try. Relationships require intentionality. Some people call it "rules". Some call it "strategy". Some call it "games". Call it what you will. It helps to have a loose plan, some guidelines, and a solid understanding of human behavior. Yes, sometimes it just clicks. But when it does, it's because both people's behavior fell within the spectrum of the "rules" and both naturally played their "stategy", even if it was not thought out but purely based on emotions. I say, better to go in with some thought put into it.

And know when the rules were made to be broken.

Ah. Felt good getting it out. But I having a feeling I may pay for it. πŸ™‚


Ms. Single Mama February 9, 2009 at 1:19 pm

No, you know what? That makes total sense.

I guess I do have some kind of strategy – mine is to get to know him and even see if he's dateable! Simple as that really. But I think your explanation is more fitting for men because your brains operate differently.

But as a man, you should hope the female feels something outside of any rules and strategies pretty early on – otherwise you're toast.


Susan February 9, 2009 at 2:01 pm

Midwest Irish Guy is right! Just be yourself and have fun. The good news is, regardless of how it goes, it's just a date — either the start of something promising or only a few hours out of your day. It's ok to be excited…but don't think too far ahead about what it all means, if you know what I mean!

Practically speaking, ask questions of him, but try not to bombard him like in an interview. (Although, really, it's almost the same thing but with better atmosphere?!) Listen to his answers. Note the kinds of things he asks you, too. That will help you get to know him better. And, the only other thing I would say is if there is even a hint of chemistry, a hint of ease that you like, but you're on the fence about a second date, go on that second date. I wasn't 100% sure of what I was feeling after first meeting my beau, but eight months later I can assure you all the dates were worth it!

Good luck!


Ms. Single Mama February 9, 2009 at 2:22 pm

Everyone – read Susan's comment (at least twice).

Thank you! Awesome advice – the kind I will gladly take. And I'm SO happy for you on finding a good one.

And I know exactly what you meant about not thinking too far ahead. Having a blog like this makes it weird, because although I'm writing about it a lot – I'm not obsessing over this date at all (the outfit – maybe) but not the date.

So while the date is in the spotlight here – it's not in my mind.

Does that make sense?


mssinglemama February 9, 2009 at 2:39 pm

Come back and let us know how it goes!


littlemansmom February 9, 2009 at 3:19 pm

I'm proud of you….being YOU is the best thing that you can do!

Horror stories…oh ya, many.

As for advice…relax, be yourself and be prepared for a second date. First impressions are rarely the REAL , it's only after the pressure that you truely begine to *see* who you are dating so give a second or third date a try and use those as the 'first' impressions…


wyliekat February 9, 2009 at 3:24 pm

I don't know if I have any worthwhile date advice – I've never really thought too much about how I am in that context. I basically just chatter away, and see where things go. Even in dates where I wasn't all that interested, there was still good conversational flow. But then, I'm perfectly willing to be very impish and ask a lot questions – last meal, best movie ever, cats/dogs/other, etc. I'm always up for a friendly disagreement about the relative merits if "this" last meal vs "that" last meal, or how much better dogs are than cats. It's good natured, if you keep the questions to things of this nature – it's stuff that most people have a strong opinion about, but rarely take too personally. The friendly disagreements (if they happen) lead to a lot of fun sparks, which is always a good way to pass the time.


Laura February 9, 2009 at 3:37 pm

You have gotten a lot of great advice and I agree with a main theme in all of the comments…Be Your Self.

When I have gone on first dates I never put any expectation on it (ie looking for a husband or new boyfriend) the only thought I would have is "hey you never know this may be the start of a great friendship". In my experience as a single mom I have never met a man that had an issue with me having kids (3). It may be my age since most men in my age group have a child or two themselves. Sooooo talk about your son because you are right he is the biggest part of your life. Odds are this gentleman will ask you about him anyway.

Bottom line…just have fun…its an evening that you can take the mommy hat off for a few hours…enjoy it!


Lisa D February 9, 2009 at 3:47 pm

Very exciting, Alaina! Everyone else has already given great advice!

For me, one thing I pay attention to when going on a date is how he treats the waiter/waitress. Maybe it's because of all my years of waitressing in college? I just feel like it reveals alot about the person. Are they forgiving of little mistakes that might happen? Do they talk down to them? I think I read somewhere that the way a person treats the waiter is a good indicator of how they might treat you down the road… It's just one of my weeding techniques.

So excited for you. It's fun to have a date to be excited about. πŸ™‚


Rebecca February 9, 2009 at 7:12 pm

Exciting! My first date with my current boyfriend was great, but I could not have been more nervous. I don't know what was wrong with me! You're absolutely right, if there's a click, it will happen. Just be yourself πŸ™‚


MorseMusings February 9, 2009 at 8:09 pm

Lisa D mentioned "weeding techniques" and I'm kind of peaked over hearing more about those. My last date talked so very much about himself in a totally rehearsed way … I was stunned bored. The most fun I had was in getting dressed for the date.

Seriously Alaina, you could show up in what you wear on laundry day.


TJack February 9, 2009 at 10:31 pm

I'm with Midwest Guy. As a guy has recently started dating a single mom, its so refreshing that she is just herself. If there's any chemistry at all, its a cake-walk. He'll let you know he wants to see you again, and you already said that you would do the same.


Canadian Bald Guy February 10, 2009 at 1:27 am

Not much more I can mention that people haven't already said. Just be yourself…if it's there, it's there. If it's not, c'est la vie.

Best of luck…I think it's great that Mr. Plane Dude is up for the date. Got my fingers crossed for you.


Victoria February 10, 2009 at 3:05 am

Ooo- have fun!

My first single mom date was a lunch date, and while I was a little nervous, I went without any plan or agenda, other than to enjoy a couple hours with a grown-up πŸ™‚ I ended up meeting a nice guy and a great father, but unfortunately the chemistry just wasn't there. I'm not afraid to keep trying until I get it right, but I will always just be who I am.


casanova February 25, 2009 at 12:27 am

Ok ladies, 4 dates in 2 weeks, is that too much? We never stop talking and 3 of the 4 were GREAT dates but I am questioning whether or not she is interested. She has held her cards tight. She answers my calls, and my text messages, and she texted after date 4 to be sure i got home. We exchanged a few more texts that same night, all intiated by her. But do I hang low, and wait for her to call/text again. In my heart of heart I know she is interested and wants to be courted…but does she?


mssinglemama February 25, 2009 at 12:51 am

Nope. Call her… DO NOT text her. Wait one or two days since the last date and call her to make plans for the next one. For sure.


Casanova February 25, 2009 at 3:54 am

Any signs I should be looking for either way?


mssinglemama February 25, 2009 at 5:06 am

Call her and see if she answers or calls you back. That's a sign for you. Rip that bandaid off my friend. What are you afraid of? Just do it. One phone call isn't going to make or break her … if she likes you, she likes you.



Casanova February 25, 2009 at 1:15 pm

Very true, very true. I guess I've been playing the game, which I hate, and vow never to do, by thinking I should wait all week to call her. Silly. Its been 3 days since the date, its time to call. She wouldnt have texted me after the date and had a text conversation if she was not interested, in my own opinion.


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