Questions to ask a first date

Thanks to Baking Suit for sending a link to this post at Lovely Serendipity. Though the blogger admits that she wouldn't "actually have the balls," she has listed the questions she'd like to ask on a first date.

My favorites:

• How fast do you reply to texts? I'm a very impatient bitch and can't wait for more than 10 minutes.
• Can I add you on Facebook and tag you on my latest 'check-in' status?
• Can you deal with my mood swings and not complain about it.... EVER?!
• Will you guest post on my blog someday? [<--My absolute favorite!!]

Most of her other questions don't apply for my dates (seeing as I'm old enough to be her mom, this is probably to be expected). But some questions I would love to ask:

• Do you talk in text speak? Do you know the difference between to, too, and two? How about
  
  their, there, and they're? If not, tell me now.
• How do you feel about dating someone who writes a dating blog? [<--Followed closely by, "Will you write a guest post?"]
• Do you support same sex marriage and a woman's right to choose? 
• Will you let my cat sit in your lap and sleep on the bed? 
• Are you actually going to call after this date? Or are you just saying you will? Don't lie.
• If you are not going to call - at what point during this date did you make that decision?
• If you are going to call...you're not clingy, are you? How many times a day do you "check in?"
• How long do your relationships usually last? 
• When did your last relationship end? 
• Did you Google me before meeting? What did you find?
• ....and so on.

It's true that sometimes the opportunity to ask some of these questions does present itself. Not always directly, but certainly politics and past relationships do sometimes come up on a first date. 

I feel like we all go on first dates (or initial assessments) with a list of questions to which we want answers. The trick is working them into the conversation, so it doesn't seem like you're interrogating the guy.

Maybe I should just lead with, "Do you mind being interrogated?" 

Bad date gone worse

I have "met" a bunch of guys recently. By met, I mean exchanged messages and/or texts. Mostly it hasn't gone any further.

Last weekend, though, I was invited out on two casual "first meetings." I honestly wasn't looking forward to either, but they both seemed like nice guys, so I figured it couldn't hurt. . It was a nice day to be out and about, and meeting new people is usually interesting, if not always fun.

Found it here

Date #1 arrived at the coffee shop right on time. He walked in, said hi, and then immediately excused himself to put his suit coat back in his car, because I was dressed casually. It was a Sunday afternoon, and I'd just come from an afternoon of volunteering in the park (which he knew). I was casual, but certainly not messy.

I found that to be a little awkward...but I moved on.

He started asking me about my previous relationships. I can't say enough how much I hate when people do this. Yes, if we're dating, previous relationships should come up. But shouldn't you want to know me before you get to know them?!

To make matters even more uncomfortable, he asked what had gone wrong in my long-term relationships since my divorce. I said that both men (Big and Trooper) had just come to the realization that I wasn't the one they wanted to be with long-term, so they ended things.

It's the simple, easy answer. It also happens to be true. So you'd think that would satisfy a person's curiosity.

You'd be wrong, though.

He's a counselor - so he switched into counselor-mode and asked if I'd ever spent any time thinking about what might have happened? More importantly, had I tried to figure out what was wrong with me that had made them change their minds?

I looked up from my salad (which I was now plowing through in an effort to bring this date meeting disaster to a screeching hault) and said, "No, I just figured they were both jackasses." Perhaps an over-simplification, but it seemed like the quickest answer.

I'm not a counselor, and I don't claim to be a dating expert (if there is any such thing). Still, it seems to me that it is bad etiquette (and a bad idea) to suggest to someone you want to date that previous relationship failures were her fault.

He switched gears at that point, and said it seemed like I have all the qualities he's looking for. I reminded him that we'd only just met, and asked how could he possibly already know that he's interested? He responded by explaining that if he wasn't interested, he would have known right when he saw me, and turned around and walked out of the coffee shop. He would have pretended he was someone else, didn't recognize me, and just left me sitting there.

I think - I think - I was supposed to feel flattered that he found me attractive enough to come in and sit down. I think.

I wasn't flattered. I also didn't have a response.

When he walked me to my car, I told him it was very nice to have met him, but that I didn't feel there was a connection (he asked). I also thanked him for lunch.

First dates are not dates

A couple of weeks back, after going on what feels like my thousandth first date since I started dating after my marriage ended (which was really only four years ago, though it seems like an eternity), I came to the following conclusion:

First dates should not be called dates.

Yes, I know we all want them to be "dates" because no one wants to feel like the guy she likes is doing something other than dating her. Yes, I know it's a big deal to get a guy to even use the word because they seem convinced it commits them to some sort of indentured servitude. It is already next to impossible to get a guy to admit we're even on a date - and here I am, taking the word away and making us one outing further away from a relationship. 

But hear me out. 

The first time you meet someone, you don't even know if you like him. Sure, you know enough to know you want to meet him in person (assuming you met online), or you liked him enough during that first chance meeting to set up something a little more formal.

But you don't really know if you like him. You don't know how he behaves in public, how good he is at conversation, how he'll treat you, or how he'll treat others. You have no idea how much you enjoy talking with him, or if his jokes are too corny or goofy - or just the right amount of both. You don't know what type of future you might want with this person, other than the hour or so you're willing to devote to finding out if he might be worth more. 

There are no romantic feelings at all - yet "date" implies that there are. It implies that you have decided you can't wait to see him. It implies that he is worth a new outfit or super-uncomfortable shoes. That he deserves your best perfume or the few extra minutes it takes to do your eye makeup just right. 

You don't know any of that yet, though, because you haven't even met him. How could you possibly know if he's worth all that time or effort, until you've had a chance to talk and get to know at least a little bit about him? 

Until you get to that point, it's not a date. It's just a meeting. Or as Baking Suit suggested, an "initial assessment."

Little tests

My date wasn't with "Know games" guy -
but hiding still looks pretty good.

I was on a date this weekend. He suggested meeting half way, and driving together to a restaurant he likes that is about 90 minutes away. Normally, I don't do the whole ride-together thing on a first date. I've been talking to this guy online for a while, and had an OK vibe from him. Plus, I liked the idea of me saving on gas.

Safety isn't the only concern, of course. Riding together, and traveling that far, pretty much guaranteed the date would be at least four hours long. Trapped with someone for all that time, with no idea how conversation would be? That was the real problem.

I started noticing comments that made him seem...a little old-fashioned. It's tough to explain, but he was coming across as very opinionated and rigid. He definitely did not have a lot of education, and definitely blue collar. I don't really care about any of that, but those things sometimes add up to a person with whom I might not share some political or social ideals.

So, I brought up an incident that happened in my city recently. It was a domestic disturbance between two men, who were also a couple. I figured the story might be a good conversation starter (or filler) but also give me a chance to observe his reaction to a gay couple.

It wasn't positive. Actually, I think he scowled.

At that point, I was pretty much done (which was unfortunate, because we were only half way through dinner and still had an hour drive together). Even if we got past the lulls in conversation, it appeared my instincts were right, and we differed in some very key ways.

It occurred to me that we probably all do these kind of tests on dates. I don't just do it with issues - I also do it with how a guy treats me. If I mention I have bad knees, will he remember, and offer to get the car for me or help me down a curb? Will he walk on the curb-side of the sidewalk? Will he let me order first? Does he grab for the check right away? Is he nice to the server?

I'm sure everyone guages behavior differently. The point is, whether we realize it or not, a first date is really just a series of tests. A chance to observe how the other person carries himself (or herself), and to try and predict how well that will mesh with our own behavior.

I'm sure he's a nice guy. He may just be too down-home, good-old boy for me. Or maybe I'm too snobby, white-collar bred for him. In either case, we're not a good match.

And I'll be sticking to coffee for first dates from now on.

Thanks, hon

My friends will tell you that I'm a stickler for etiquette and respect. It might seem old-fashioned to some, but I just think that there's something to be said for observing a defined guideline for how to behave in a given situation. If you think about it - many awkward, angry, and sad moments could be avoided if people would just mind their manners.

First dates are a prime example. Most of the time, you don't know each other very well - if at all. Even if you've been talking for a while, it's a first date - so it's probably the first time you're meeting in person. That also means it's your one-and-only chance to make that first impression.

If you don't know the person well, it's hard to predict how he will react to certain behavior (running late, texting while at the table, offering to pay). If you know the proper etiquette (don't be late, don't talk on the phone, let him take the lead on the check) at least you have a place to start.

Some things are less obvious. I mean, anyone can put their phone away on date number one. The real truth comes out on date number twelve, when both of you have your phones sitting right on the table. But there are little subtleties in people's behavior that can be really telling about exactly who they are.

Like, showing up for a Friday night date wearing dirty sneakers. (Why do men do this?!) Our date is not at the gym, or a walk in the park. We met at a restaurant. For drinks. Wear shoes. Don't own any? Do us all a favor and stop dating.

Or how about having something to talk about? We're both on this date (which, by the way, you asked for) - why am I doing all the work? If you don't want to be here, that's fine with me. I've got stuff to do.

Want to split the check? Okay with me (Disclaimer: It's not okay with all women, so tread carefully here). But by split, I mean we each pay half. I don't mean for you to sit there and review the check with the waitress, itemizing which items you want her to tally up and take out of your $20. Mortifying.

Unless you know the person you're with, and/or the waitress is related to you, you really shouldn't refer to her as "hon." See - some women (ahem) consider that to be very condescending and disrespectful. Now, I expect you to treat me well, because you're on your best behavior. That's fine - but just know I'm paying a lot of attention to how you treat others, as well. It tells me a lot about what you really think is acceptable treatment of the women in your life.

So, thanks - hon - for the heads up. At least now I don't need to waste anymore time on dates with you.

One-hit wonder

So I know I'm supposed to be thinking positively and not getting down on myself. But sometimes that's easier said than done.

I finally met Mr. Ding-a-Ling (I literally giggle every time I type that). Turns out, his current work situation, along with a part of his family situation, has him somewhat between permanent homes. He has a stable job, and is living out of ridiculously nice hotels while that gets squared away. By no means does he not have his act together (just the opposite, actually), but his current circumstances did make it challenging to schedule a date.

After he cancelled our first plans, I asked for a little reassurance he was still legitimately interested in meeting me - and that he wasn't just looking for a hook-up. While I understand sometimes that's all something ends up being, there's a big difference between just ending up as a "friend," and going into it with that expectation.

Found it here

I felt pretty confident that we were on the same page. That being the case, I agreed to a date that would require me driving, and meeting him when his work would bring him close enough to my area. So I did. This also meant our first date would have a very awkward, she-drove-all-this-way-should-she-stay-in-my-hotel-room component.

I didn't want that. First of all, the absolute last place I ever want to be is somewhere I'm not wanted. I would absolutely not want for him to feel he was stuck being hospitable because I drove a ways to have dinner. If we're not clicking - we're not clicking. If that was the case - I also wouldn't want to feel trapped. Nothing like a good hostage situation to ruin a perfectly good meal.

He asked me point-blank, "Is your plan to stay or drive down and back that night?" I told him I'd come prepared to stay, but we could decide that night if it made sense for me to do so. The truth is, I'd have gotten back in the car and gone home; and the reality is, my cousin lives about 15 minutes from where I was, so I had a very safe alternative.

I told you - it may not always seem like I have my stuff under control, but I usually do.

All I'll say is: It was a great first date, and went as well as I could have hoped. We talked, we laughed, and we had good food. He shares my love of all things sweet (yay!). He also shares my love of technology and had no issue with me checking my phone (double yay!). He's so incredibly good-looking I had to force myself not to stare at him. Or drool in my pasta.

After the date was over, though, I found myself wondering...now what? His schedule makes it so hard to plan dates, it's not like I can text him in a day or two and see if he wants to get together again. That fairly simple, innocent question - "Do you want to do this again?" - usually helps answer the more complicated, underlying question - "Was our date a one-hit wonder, or the first in a string of potential hits?"

In other words - I like you; do you like me back?

Even though we've been talking for a few weeks, and have both said we feel like we've known each other forever and feel very comfortable with each other, it's not an easy question to ask. At least if you can just keep making plans, it sort of evolves naturally.

I suppose I could wait and see. I mean, I'll either hear from him again, or I won't. If I do, I could just say, "Are you interested in getting together again sometime?" His answer would (with any luck) lead to a more in-depth conversation about where we both see things going (or not).

But who are we kidding? We all know I suck at waiting.

Who is the jerk?

"I single-handedly blew it," she said.

She was at his house, after a great third date. One thing led to another, and after some really awkward first-time sex, she lay in his bed, unable to sleep.

No goodnight? No kiss? No nothing. He'd gotten what he wanted, took a quick shower, made himself a snack, and went to sleep. Her staying was more of an afterthought than an invitation.

She felt icky, and irritated. Mostly, she just wanted to be in her own bed, far away from what was feeling more and more like a big mistake.

So, she got up and left.

She told herself that she wasn't waking him because he was tired. But as soon as she got in her car, she realized that wasn't true. She didn't wake him because she was angry, and hurt, and didn't know how to bring it up. She left because she couldn't stay next to him without saying something.

She texted him to explain, and apologize. He replied the next morning, saying that he was hurt and needed to "process" what had happened.

She felt lousy - and told her friend she'd managed to single-handedly ruin something that could have been good. I was asked, so I'm sharing my take:

They were both wrong.

Sure, she should not have bolted. I mean - in all honesty, unless specifically invited to stay, I have never spent the night after the first time. I feel like it sets a bad precedence that I will always want/expect to spend the night. I don't. I have a life; it includes my own bed, my own closet, my own shower, and my cats. I got stuff to go home to, ya know? Besides, there's plenty of time to work up to the sleepover.

But when I leave, I certainly say goodnight, and I think she should have as well, even if that meant waking him. If you can let someone put his parts inside your body, you should be able to shake him on the shoulder. But hey - we've all been there. She was probably caught off-guard, not knowing what to expect. Before she realized what was happening, she was laying next to some guy snoring away, while she tossed and turned. She panicked. It happens.

But what about him? Quick, all-about-him sex, a shower and snack, and he just goes to sleep? That's their first time? No freakin' way. You only get one first time at anything - and you're supposed to put your best foot forward. Allowing for awkwardness isn't the issue...he was flat-out rude. If that is his best foot, I'd hate to see what might happen after they became comfortable with each other.

As for him needing to "process" her apology and explanation, here's how I read that:

I have to process = 

I got laid, and didn't even have to figure out how to kick you out. 

As a bonus, you feel bad enough that I can blame you for the fact that I'll never call again. 

Score!

I know that might seem harsh, and maybe it's a little unfair (I don't even know this guy), but I mean - c'mon! The woman was, at the very least, his house guest. He must realize he should be considerate and kind and polite? Surely he was taught better?  

My opinion is that this guy owes this woman as much of an apology as she owed him. 

The fact that he hasn't offered that apology tells me that what she really ruined was the chance to keep dating an inconsiderate clod, who apparently can't even spell the word "orgasm." 

I don't consider that a "ruined" anything. I consider that a bullet dodged.

New-outfit worthy

"I can always tell when you're going on a date. You always look nice, but when you have a date - especially a first date - your outfit is new."



Mr. Ding-a-Ling - now even more appropriate

This observation (about me) is at least partially right. I do like new outfits, and I do my best to put together a really good outfit for a first date. If I start seeing someone, I go to great lengths to make sure he doesn't see the same outfit twice, at least in the beginning.

But I don't always buy a new outfit. I am slightly more fiscally responsible. Nowadays, I will only buy a new outfit if a guy seems really, really worthy.

Last week I met a guy on Plenty of Fish that I thought might fit the criteria.

He's ridiculously, out-of-my-league good-looking. He seems smart, and funny, and gets my humor. He's good-looking. He has a good, stable job, and says he's ready to find something more long-term. He has kids, but they're grown. He likes pets. He likes the wrong baseball team, but nobody is perfect. Did I mention he's good-looking?

He travels for work, and was out of town all week. We made tentative plans to meet on Friday. His suggestion. Earlier this week, he told me he comes back in the area on Thursday (I assumed late).

When I tried to confirm (with only two days notice, which I don't think is unreasonable) if we were on for Friday, he said,

"Depends on what time. I might not get back to the area until late."

Now - I don't even know this person. I'm certainly not going to call him out on what could be a legitimate schedule change or mistake on his part. Maybe he read his calendar wrong. Maybe he just found out about a stop he has to make on the way back that will mess him up. Who knows?

Doesn't really matter - if he is blowing me off, that will be perfectly clear on Friday. I will have lost nothing. He asked if I minded "keeping it open" and I said I would keep it as open as possible - but asked that he not leave me hanging. I'm not giving anything up by keeping my schedule open, so we'll see.

I don't know enough about him to know for sure if he's playing a game, giving me a line, or is being honest.

The one thing I do know for sure? He's not new-outfit worthy, no matter how good-looking he might be.

First time sex

Recently, in two completely separate and unrelated conversations, I was told by two people who don't even know each other (and are practically from different planets), that "first-time sex is always awkward."

I'm no expert, but I have had my fair share of first-time sex. In my experience, it isn't always awkward; it is sometimes awkward.

It's really no different than a first date. I think we can all agree that most women probably have more first dates than they do actual relationships. When you meet someone, you think there might be a connection - but there's no way to know for sure until you go out. But for all the first dates we have, few lead to a second. Even fewer lead to an actual relationship.

A lack of conversation, or a disagreement over the date activity, or a boring time, or whatever is a sign that it just isn't going to work. This relationship isn't meant to be - and that's fine. We gave it a shot, and now we know. Rarely do we invest so much in first date that we get upset if it doesn't work out. Really - nothing is lost (except maybe a few hours and a few dollars, which is really just a cost of dating).

Sometimes, first dates eventually lead to first-time sex. Personally, I think if it's awkward, that's also a sign. Just like the signs a date isn't going well, awkward sex is a sign that you have different desires, preferences, fantasies, or rhythms. Whatever it is, you're just not in sync.

That should be fine, too.

Just because you got to the point of wanting to have sex does not have to mean that he is The One. You have to keep looking if you're going to find him, right? Sex is just a part of that search. It would be an important part of any relationship you choose to pursue.

Sure, if you've decided to wait until you're married before having sex, and your first time is awkward, then it's something to work on. But if you're having sex early on, why is it something you have to "give a chance?" If you found out that the two of you wanted different things out of life, or a relationship, or finances, or family, would you try to "work it out?" No? Then why give the sex a chance?

Maybe the awkward sex is just the the sign we need to know it's time to move on. I think we need to cut ourselves some slack and realize that while we're looking for Mr. Right, we're going to have sex with a few Mr. Right Nows. It doesn't mean we're sluts, or have poor judgment, or make mistakes.

It means we're trying to find what we want, and what makes us happy, and we know that sex is a piece of that puzzle.

*Note: Yes, I encourage casual sex and/or sex early on in a relationship. I think it's important for women to know what they like, and casual sex is a good way to learn. I also believe sex is an important part of a healthy relationship, and you need to know if it "works" with a person before the relationship continues. However, I encourage safe and responsible casual sex. Safe means protecting yourself; responsible means being honest with your partners about your situation, including if you're not monogamous.

Expiration (on the) date

When I told you about the two-date night, I mentioned that I liked a place with quick service for a first date. When I explained about date number one from that night, you understood why.

Thing is, it doesn't matter if you meet your date online, or at a bar, or at a church mixer. The truth is, you don't really know how a guy will be on a date until you're on the date. By then, unless you've planned ahead, it might be too late to save yourself.


I've been on bad first dates. There was the guy who suggested the restaurant, then handed me the bill; there was the guy who left the theater to take three separate phone calls; and more than one that nearly bored me to tears.

They were all different dates; parks, movies, dinners. What they all have in common is that there's no real time limit. If there's one thing I learned from last summer's dating marathon, it's that a first date really should be short and sweet.

I like something with counter service (like a coffee shop). If you want drinks, I suggest meeting at the bar. Why? First, it eliminates the need to wonder who is paying. In either situation, you can order (and pay) separately.

It also slaps an expiration on the date. Coffee's done? No reason to stay. You met for coffee because that's what you had time for - a cup of coffee. Having met your obligation, you can get to that next thing on your schedule - whatever it may be. "I have to run...things to do....meeting my friend the police officer...." Whatever.

You're not at the mercy of a slow kitchen, and you don't have to wait for the waiter to bring the bill. You don't have to wait for the credits to roll, or figure out a way to steer the "walk" back towards the car. Having transacted the business-end of the outing up front, you really don't even have to finish your latte. Just make sure you get it in a to-go container.

But, if things are going well? You're still open to more date. Suggest a movie, or ask if he wants to grab a bite. In a mall? Ask if he wants to walk a bit and window shop. Near a park? Maybe there's a free concert or something else going on.

Leave yourself the option to continue - or end - the date on your terms, instead of someone else's schedule.