Is it okay to ask a man out on a second date?

by singlemomseeking on January 15, 2009

This post is for the folks who are tired of hearing about The Bachelor, you know who you are!

One month after posting “The man I hope to love,” I put myself back online. I was ready to date again.

Or, so I thought — until I went on a few bad dates and wanted to hide again.

Then, I got this email from a guy who’d emailed me when I was previously on JDate, in 2007. We’d had a string of emails back and forth, and then shared an awkward email moment: both of us confessed that we’d just begun dating other people and were going off JDate.

My gut, however, told me that he was a good guy. So, I sent him my direct email. (He didn’t write back, which he explains below.)

“There you are again,” he wrote to me recently. “I found our messages from a while ago. I have to say, your last message was very sweet, and I did consider writing you offline, but we had both starting seeing others, and so I declined…. Anyway, would you be interested in a chat?”

This time, I sent my phone number to him.

He called during the day, which can be an awkward time for a first conversation. But it was spunky, fun, and smart. Some of you also know that I’m a sucker for a deep voice.

What was the problem, then?

I didn’t know what he looked like! Sure, he had a few photos online — but he was wearing sunglasses in two of the photos, and looking down in the third. What was up with that?

He emailed me the next day to ask me out for dinner and a play. That was against my “first date rule” — only short coffee dates for the first meeting — but I promptly broke that rule.

“You’re so cute!” was first thing I said when I saw him. He’s intellectual-looking, with glasses and a goatee.

I wanted to know: “Why are you wearing sunglasses in all your photos?”

“But I like those photos!” he said.

Within two minutes, we were having our first fight. But it was a sweet, affectionate fight.

Our first date was filled with fun, insightful conversation. The night ended with a brief hug on the street corner — and the quickest peck on the lips.

During the date, I’d told him that we’d just celebrated my sister’s birthday that afternoon. He’d asked why I hadn’t brought him a piece cake.

The next morning, there was an email from him:

“Rachel, You’re quite something. I had a wonderful time with you tonight.”

I was bringing him some cake that afternoon for sure! (I hear some of you now: “Slow down, Rachel!”)

I emailed him about the cake. He wrote back:

“Rachel, if you ever want to see me again, you bring the cake.”

(His sense of humor is very similar to mine, extremely dry.)

Then he gave me his home address.

I told him, “You’re giving me your address, you don’t even know my last name! What if I’m a crazy lady?”

Do you know what he said?

“You’re a mom.”


I left the cake on his doorstep (he wasn’t home), and he emailed to thank me.

But here’s the deal: he hasn’t asked me out on a second date.

Four days have passed since our first date. No more emails, no phone calls.

Now what? You know that I encourage women to ask a man out.

I want to! But unfortunately, my assertiveness has scared men away in the past. I’ve come on too strong, too fast. I’m afraid my boldness might mess this up.

Should I ask him out on a second date?

What should I do? Or, not do?

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{ 62 comments… read them below or add one }

andieeast January 16, 2009 at 4:49 pm

OH PUHLEASE! What year is this? What Century?

If you are excited about him then ask him out again. If he’s not as excited about you as you are about him, then asking him out again will not change that. I think this whole game stuff is STUPID. people should both be excited about each other. I mean don’t ask him if your daughter can call him dad and I wouldn’t reccomend giving him a ring but a piece of cake? Be yourself, be honest, and ask for what you want. That’s the only way you’ll ever get it. And if he doesn’t have it to give? Nothing is going to change that.

listen to your heart.


SDMktg January 16, 2009 at 3:06 pm

Im amazed at how many responses there are here. I think Bonnie has a point. The guy also could have been joking about the cake and got freaked out when you brought it to him. I made a similar comment about the heart shaped lasagna.

I once told a girl on a second date that I really like Coco by Chanel. The next date she was wearing it. “For me,” she said. That’s an expensive perfume and I wasn’t happy she went out and bought it for me, I was freaked out. It was over the top.

I had the “she’s just not that into you” thing with a woman I dated a few years ago. She was a busy attorney and our dates were sporadic along with a couple of cancellations. I finally just point blank asked her what was going one. As many have said, single parents don’t have time for the games. I got my answer and I moved on.

You definitely don’t need to try so hard. I’m surprised there isn’t a line of men waiting to take you out.

SDMktg´s last blog post…Playoff Tailgate Recipes PART 1 – Philly vs Arizona


Dora January 16, 2009 at 12:04 pm

Rachel, you will never be pursued if you don’t allow yourself to be pursued. Sit on your hands! No more emails or calls. Believe me, I have been where you are, and you are only torturing yourself. You’re hoping for comments that will give you permission to do what you want to do, despite the fact that it hasn’t worked well in the past. That you are twisting yourself into knots after one date should tell you something.

Dr. Leah’s advice is spot on, especially this:
“there are some men (and women, too),who enjoy that first date whirl, but then disappear. They give “potential relationship signals”, but there’s never any follow-up.””

Also, and not to come down hard on you, but there are good lessons here, I think dropping off the cake was a BAD idea. TOO MUCH, TOO SOON! The cake conversations between you were flirty banter. Should have been left at that.

And, YES, getting worked up because you haven’t heard from someone in 4 days after a first date does come off as needy. Sorry. Really, I’m sorry. This is hard stuff.

Dora´s last blog post…Pay it Forward Fridays — Vote for The Stirrup Queen!


Apples January 15, 2009 at 11:58 pm

I think this might be the reason I don’t date really. I am not the best game player.

If it was me. -And we all know it wouldn’t be seeing as I don’t date ha. Anyhow, I am so casual about things. I’d call or email just to say Hi and ask him what he is up to. Then say something like yeah cool. I got a babysitter and am headed out to the bookstore (or whatever) you could join me if your up to it.

I’d do this because 1. I am tooo chicken to be totally blunt and 2. I know I would beat myself up about it forever with the “what ifs”

Good luck keep us updated. If all else fails just tell him that your a blogger and send him a link. HAHAHAHA 😉


Bonnie January 15, 2009 at 9:49 pm

Seriously people. Have we lowered standards so far that we miss the obvious of thanking people?

Would you marry someone and cook for them after working all day and be ok without being thanked?

Or what about when you bring your partner a glass of wine, beer or snack after kids and homework and dinner, etc and you never thanked each other? For goodness sake if they don’t start out doing it what do you think will happen later!?

Rachel — do your next post on standards and expectations for yourself and love. How do you want to be treated in your next marriage/relationship/hookup? What do you deserve?


Bonnie January 15, 2009 at 9:37 pm

Yes, he is the douche bag and playing a power game with you. He got you to bring the cake literally to him. So he could have his cake and eat it too without having to do anything.

He also now has the power over your mind right now and he knew he would if you brought the cake over. These people that are making excuses as to why he has not communicated in four days are making excuses for him. Stop.

Do you want to be in a relationship with a game player or poor communicator?

I hope not even though games can be fun sometimes, but only when it is reciprocal flirting. Listen and listen from a gal who dated way too many frogs is a close age to you and my kiddo to yours. The man that will be worth your time, thoughts and sharing cake with will pick up the phone (no text no email) or just come over to see you because he will put you at the top of the list which is where you want to be and deserve to be.

Take this from a gal who ALWAYS got the call or visit from a very busy attorney even when both his daughters were very ill and he was taking them across the country to doctors. He had legitimate excuses if he wanted for not calling for months or ever. I think as far as I can tell from the comments that maybe only two of us are remarried and we married fellas that stopped the games. Your time, love and energy are precious gifts so don’t ever waste them waiting or fretting over a guy who didn’t call and ask you to come over and share that slice with him.

Worse- he didn’t thank your busy mama self for taking the time to bring him a wonderful piece of cake.?

This automatically earned him Gun’s and mine “dbag” label. Manners are very important so you can send him an email telling him you don’t do guys without manners. Imagine if you slept with him and he didn’t thank you, ugh. This lesson I had to learn. If a man doesn’t thank you then just keep moving, esp for sex. So important to thank people and to share for sharing themselves-kisses, hugs, sex, cake…whatever. So important to literally thank each other.

No one had ever done that with me before and after I could never be with a partner who didn’t. And if it feels so amazing when you both thank each other. Like better than that sacred kiss after awesome lovin’. So good.

Try it folks. I thank the man who has taught me that everyday.


Love Coach Rinatta January 15, 2009 at 9:31 pm

Rachel, you are very welcome. I am glad to have found your blog. I like how open you are.


GLSD January 15, 2009 at 9:07 pm

HI Rachel, I’ve been reading but was having problems posting a comment. I think the ball is in his court. You had a great time, you delivered cake, he emailed you a thank you, and now you emailed him to see what’s up. He knows you’re a single mom with no ex so he can’t assume that you’re available at the drop of his hat. In the email was a friendly email? did you tell him you enjoyed the time you spent with him? If so, then give him the space. He probably has a valid reason as to why he hasn’t been in touch… the 3-4 day rule, too busy at work?! give him the benefit of the doubt. Keep us posted! I’d love to hear!


judy January 15, 2009 at 8:56 pm

you’ve read the book now see the movie…but not till February “He’s just not that into you.”

Men know how to dial a phone and send an email when they want to. He knows you are interested. Wait..wait…
and you are in good company because I am waiting as well…..I say give it six weeks (real lime six weeks is guy time six days is chick 6 months) then give up.

I challenge you. Who will hold out the longest. My DD is gone this weekend and next weekend….


T January 15, 2009 at 8:22 pm

I’ve waited this one out to see all the responses too.

I don’t know Rachel. I’m just like you. I come across as aggressive I suppose to some… only because when I see something I want, I go for it. I am also tired of being the driver in relationships. It would be nice to be pursued.

That said, I’m the type of girl that tries to stay in the moment of whatever I’m doing. And, like Leah suggested, I believe that there are no mistakes. So, if I were in your shoes, I would continue to go about my life and make another plan for Friday night (or even alone… because I need it!).

It sounds like you’ve already shown interest. It would be nice to think that he’d pick up on that but males and females don’t always speak the same language.

Me? I wouldn’t take it personally that you haven’t heard from him. I know that my life is busy and sometimes things happen. If you think of it that way, like you’re checking in on a friend, then you won’t sound any kind of “needy” on the phone. You’d just be checking in… as a friend…. Why? Because “You’re a mom.”

I’m serious! I’d use that line again with him! :) Be playful, lighthearted and fun with him.

I would tell him again that you enjoyed your time with him. Play it off as friendly. Then see if he initiates the asking out on the next date. If not, then there’s your answer.

And if he doesn’t, then you’ll have just been a concerned friend checking in on another friend. And you won’t be hurt.

Because you are fabulous and definitely worth pursuing. 😉

T´s last blog post…That restless feeling again


AK January 15, 2009 at 7:26 pm

I’m very intrigued by all the responses…most of them say not to ask him out because they think “he’s not that in to you”…but really, you shouldn’t ask him out because you WILL NOT SETTLE for someone who does not give you what you need. You need someone who shows you they like you–consistently…who doesn’t want that?? I am in the same boat as you are…went on a great first date, but haven’t heard anything since (3 days)…I have no ex around–my time is VERY scheduled…BUT…I am going out with my girls this weekend–because I would much rather be with them and have fun, than try to figure out what “date #435″ is thinking! Hey, here’s an idea…fly to Hotlanta and go out with us!!

AK´s last blog post…Standing on the water’s edge….


Leah January 15, 2009 at 6:38 pm

Wow Rachel and all commenters. I am getting so much out of this exchange! I am kind of in the same boat with someone…and am wondering also if I should make the next move. For the very same darn reasons. I have no days off and I need to arrange a sitter in advance. Sigh. I have read the Rules and playing games just seems so weird. Is there something to it, truly?

Rachel, I truly feel that in life there are no mistakes. Whatever you do will be a learning experience, and a way to get clearer about how you want to date and be in relation with men.

Hugs to you. This dating thing is so crazy and hard.

Leah´s last blog post…Now I’m scaring myself.


singlemomseeking January 15, 2009 at 6:29 pm

Eathan: I admit to being floored by all the negative responses, too.

Asking to see a man again really does come across as needy? Whoa.

Coach Rinatta, thank you SO much. Your wisdom is much appreciated.


Eathan January 15, 2009 at 6:06 pm

Wow.. I’m surprised at how many of the SINGLE women say don’t ask him out. (key word single)

I have to agree with Dad’s House on this one… 3-4 days is nothing. If you’re expecting constant contact.. that comes off as needy. A busy professional can go a few days before catching up on their personal life.

I have to disagree with most of the women. It’s 2009.. the birth of the independent woman has past. There is nothing wrong with asking or suggesting a date. Of course, if he doesn’t accept.. then you haven’t lost anything and you can move on.

p.s. just don’t be one of those needy women. :)

Eathan´s last blog post…The Ex Factor Pt. 2


Viv January 15, 2009 at 5:31 pm

I LOVE what Love Coach Rinatta wrote. It’s so true. Did you comprehend it?? You seem determined to be let down or even hurt. And why? ‘Cause you don’t have a man in your life? So what! Get over it and definitely get over him! If he is interested, he will call. If not, it’s his loss!!


Love Coach Rinatta January 15, 2009 at 5:20 pm

I read your site daily, so I figure it was time to comment.

Ever heard of a little book called He’s Just Not That Into You? Men are the supposedly the Yang energy – the action energy – so if a guy wants someone he will go after her. If he’s ambivalent, or not sure, or what ever, he just doesn’t want it bad enough. And you want a guy who’s going to want you bad enough.

Rachel, you are so fab, you deserve a guy who’s going to chase you, not the other way around. Bottom line – don’t call, don’t hint, don’t email. Let go and move on and trust that this is a step in the right direction and the right one is out there for you.

Love Coach Rinatta´s last blog post…Can’t seem to get dating right? Calm down already!


Anita January 15, 2009 at 4:23 pm

Rachel, I belive you should do what you feel. If you want to hear from him, let him know. Seeing that it is 4 days since you have last had contact with him, he may not want to pursue anything further in which case he will let you know and you will move on.

Like this, it is like you are holding your breath without being able to exhale.

This is coming from someone who is holding her breath!! lol.

Any reply to your email?


John F January 15, 2009 at 4:10 pm

Go ask him! No guts no glory! Besides we like an aggressive woman (to a degree)


Phil January 15, 2009 at 2:59 pm

For some guys, it’s a power play to have the upper hand. Personally, I hate those games and never do it. Go rent ‘The Tao of Steve’ if you want to see it explained from a guy’s perspective.

Sounds like he likes you, he’s either waiting it out or just isn’t interested in a relationship. Don’t take any of it personally.


Nikki January 15, 2009 at 2:43 pm

I heard it straight from a man’s mouth…

“The reason I was intrigued by her was because a few days after I’d called her, she wasn’t busting down my door to talk to me again. This meant to me that she didn’t need me and that she was a strong enough woman all on her own.”

They’re now married.

If he’s worthy of you, he’ll ask you out again. If he’s not worthy of you, he won’t.

It’s not about him being worth it. It’s about YOU being worth it. You deserve to be pursued. All us seeking women deserve to be pursued.


Nikki´s last blog post…Where is the Safety Net


Erica January 15, 2009 at 2:36 pm

Oh – and about your free time Friday night, I would totally stop by and dance it out with you. If only I didn’t live a gazillion miles away.

Erica´s last blog post…Parenting Joy


Honoree January 15, 2009 at 1:37 pm

My new husband said he hated games and called the night after our first date. Hates games – me too. Sometimes we attempt to do what we think we should do instead of what we want to do. I think it comes down to what do you want to do.

Another thing to note: my husband said, “Why not kiss, have sex on the first date, call, whatever feels right. You can’t do the wrong thing with the right person.”

Honoree´s last blog post…The Successful Single Mom Principles


Kelly January 15, 2009 at 1:36 pm

I’m with 95% of the people here – the ball is in his court, and if he’s truly interested he’ll bite. No need to push… guys just have this thing where they don’t want anything that comes easy to them. They want to be challenged.

I think Bonnie’s husband was saying that him getting you to bring him cake was his way of exerting power over you to see if you’d do it.

Kelly´s last blog post…null


wandamd January 15, 2009 at 1:05 pm

Lance touched on something there…”if you feel strongly that he’ll say yes.” I think you aren’t confident that he’d say yes and perhaps listening to the gut, not matter how crappy it is, might be the best.


Lance January 15, 2009 at 12:38 pm

Ugh, four days with no contact? Not a good sign at all. Usually, if the dude was really attracted, he’d get back to you pretty quickly and maintain the momentum from the earlier meetups.

If the roles were reversed, I’d send a playful text or email, not asking for anything, but basically something fun to remind him that you’re thinking about him. I usually send emails with links to funny articles, pictures, horoscope, something along those lines.

A woman can initiate the talks about a second date no problem if you feel strongly that he’ll say yes.

Lance´s last blog post…Is Sex a Distraction or Should We All Just Get Laid?


singlemomseeking January 15, 2009 at 12:28 pm

Tell me: what is is about that “requisite three to four days to be in touch”?

Do folks really follow that? I never have. Maybe that’s my problem.

Who says that waiting is a requisite? (Dad’s House, do you seriously like it when a woman makes herself unavailable and drives you nuts? Really?)

Clearly, as everyone has pointed out here, if he hasn’t asked me out… got it.


Honoree January 15, 2009 at 12:22 pm

Rachel! I’m going back and forth between “he’s just not that into you” and he’s waiting the requisite 3(-4) days to be in touch. You’re fabulous and if he’s interested, he’ll phone, email, mail, FTD, whatever. Let him come after you and if he doesn’t, well, you’re on the right track. Him or someone better is on his way to you right now! If he hasn’t been in touch in a month, send him an email and go down the friend path. You deserve the best! Best wishes!

(P.S. Did you receive the book yet?)

Honoree´s last blog post…The Successful Single Mom Principles


dadshouse January 15, 2009 at 12:13 pm

Don’t ask him out – let him ask you. He knows you’re interested. Give him space. Four days is NOTHING. In fact, make yourself a little unavailable and drive him nuts…

dadshouse´s last blog post…Twitter is Bad For You


Mike January 15, 2009 at 12:12 pm

I would say “no” just because you already dropped the cake off. If he can’t ask you out after that he’s not worth your time. There is no rhyme or reason for his not contacting you so doing even go up that coconut tree.

Mike´s last blog post…Tobacco is Still King


Erica January 15, 2009 at 12:05 pm

I don’t think you should contact him. Your cake was your contact. It’s his turn. But then, I’m single – so what do I know? :)

This post has reassured me that I’m doing the right thing by not dating!

Erica´s last blog post…Maalox, Anyone?


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