What to do about the Expensive First Date

I grew up with men in my life that treated women well. Not to the extent they traditionally follow in the South, just that they extended a general courtesy as the man to the women in their life. I appreciate and am looking for that kind of respect in my other.

I have a hard time, though, letting a man pay for what I consider an expensive first date. I don’t think anyone should have to spend a lot of money to get to know someone and I feel uncomfortable when my date is shelling out the dough to see whether or not we are compatible at the most basic dating level.

Its hard to tell whether the gentleman is using the money to impress you, whether he simply operates on a more expensive scale than you do, whether he’s one of those “the man always pays” dudes, or some combination of the above.

How does a modern, financially stable lady walk the line between traditional gender roles and equal-opportunity dating? For me, its case by case, and sometimes I have a better read than other times.

Try to Deter the Spending in Advance: Fail
I think you should go dutch on expensive first dates if you’re just getting to know someone. I had explained this theory and desire to split the bill before I accepted a sushi date knowing we’d go over my first date limit, but at dinner my date just snatched up the check and pretended we had not had that conversation. I appreciate that he wants to pay for dinner, but I would appreciate even more if he respected that it made me uncomfortable given the cost of our dinner.

Make an Exception to the Rule: Success
Sometimes you make an exception, like when I was invited to go to a concert with someone I had met online but hadn’t yet met in person. I told him I was uncomfortable about just taking the ticket but he pawned off the expense saying he had planned to go with a friend who had bailed at the last minute, and didn’t know anyone who wanted to buy the extra ticket. It sounded sincere, and I agreed to go. The concert was incredible, and he let me buy a few rounds of beer to even things up. Letting me contribute went a long way towards making me feel better about his paying for the ticket.

I know some guys like to go big on the first date or find it offensive when gals insist on contributing financially. I know that I need to set aside some of my personal opinions on the “right” way to date and be open to the many possibilities for successful dating.

I’m working on being less uptight about the money thing, but its taking some time. In the meantime, just ask me to grab beers at a bar with great turkey burgers (and sweet potato fries for extra credit).

Failed First Dates: The Non-Caller

romantic sushi
musician who won't use phone
kicked to the doghouse

I think sushi is a great dinner option for a first date; besides meeting a new guy I would be able to eat delicious nigiri sushi and caterpillar rolls. My date was a little mushy for my taste, he didn’t feed me maki from his chopsticks, but he did reach for and hold my hand over the table while staring into my eyes for extended periods of time. We had a good time, though, and I agreed to a second date. We planned to go for a bike ride the following Sunday afternoon.

That Sunday morning, I was puttering around my condo sorting laundry and such, and I hopped on my email. He had sent me one asking for a reschedule or rain check; he needed to fill in for this musical group that afternoon. I promptly replied back that I could do late morning and to give me a call if that worked. I also called him and left a voice mail.

What happened next can only be described as insecurity (on his part) and experimentation (on mine). I replied to his emails, each time requesting he call me directly, but instead of picking up the telephone the Non-Caller sent email after email response, stating that he didn’t want to intrude on my weekend by calling me and that even though I repeatedly asked him to call him that he wasn’t sure I wanted him to, really. It was ridiculous, and culminated in him sending me an e-card the following day to apologize.

Needless to say I sent one final email, expressing that I no longer wanted him to email (or call).

Lessons in Dating: How to Cancel Plans

Its my personal belief that in early dating one should make themselves available for, well, dating. More available than they might normally be so that they can actually get to know the person they’ve started dating. Single people have lives, though, with careers, family, friends, hobbies, so its understandable that even while making dating a priority on the social calendar some plans may need to be canceled.

There’s nothing wrong with canceling plans, but there is a right way to do it. You want to do two things, ensure the person knows you’re canceling (so you don’t stand them up) and provide an explanation and/or request a reschedule (so they know you’re still interested).

The best way to do this is call them on the telephone. Its direct, your tone will be able to be heard (you’ll want to sound sorry that you had to cancel) and you can leave a voice mail if you miss your date. I would avoid email and text - they’re less direct forms of communication, and its kind of a cop out. If you’re going to bail, buck up and call the person you’re canceling on so you can tell them personally, if not in-person.

The results of not making the personal effort can be disastrous on early relationships. Case in point, I invited a guy I wasn’t sure I was interested in to join myself and another couple out for sushi. The invite was casual and communicated during the work day over email. In my last email I confirmed the time/location and asked to him to call me if he wasn’t able to make it. Then I left work.

When I got home I was intercepted by a work phone call which required logging into my computer. I happened to check my email and I came across one more email he had sent about an hour before we were to have met, saying he wasn’t able to make it.

I was pissed, mostly because if I hadn’t accidentally checked my email I would be standing outside the restaurant, being stood up. But it also felt like he didn’t care enough to get in touch with me personally to cancel, which made me feel like he wasn’t that into me. That it turn made it easy for me to decide I wasn’t that into him after all.

I’m sure he didn’t even think about it, didn’t actually read my email where I asked him to use the phone to cancel and just replied over email, didn’t realize that on his Blackberry he was just as capable of using the phone feature as the email one, didn’t feel like it was a big deal to cancel since there were other people who would be at dinner…

I asked him about it afterwards, when he couldn’t understand why I wasn’t interested in seeing him anymore. I asked him what he would have done if he needed to cancel a client lunch. Would he send an email an hour beforehand? Or would he also call that client to try to speak to him directly? He answered as I expected, he would have done both.

I told him that’s what I had been looking for. Someone who would have showed me the courtesy he showed his clients. Someone who valued my time just as he valued his. I hope he learned his lesson.

Failed First Dates: The Brit

a british import
decent teeth, off-colour wit
nothing in common

The Brit was an English journalist in the States starting up a new publication. We met through a CL post and IM’d or talked pretty regularly for a week or two before we officially made a first date.

I had high hopes that we might have a real connection. Our conversation had been fairly easy as well as entertaining. I felt the cultural difference but thought it could be fun, or at the very least would give us plenty to talk about. Besides, my grandmother is British and I’ve always loved a dry wit.

We met for drinks at an English-y pub, but even after a few delicious brews it was clear that we weren’t a match. I felt the physical connection, but couldn’t get past what became a larger and larger communication gap. Everything he meant to be funny came off as confusing and/or rude. He would say something, expecting a laugh, and I would try to figure out what he had meant without feeling offended.

Perhaps more off-putting was his tendency towards sexual innuendo. I’m all for flirtatious speak and a little bit of sexual tension - it’s what usually leads me to believe my interest is romantic and not just platonic - but his came off dirty, rather than suggestive.

Eventually we were reduced to talking about beer and petting the local dog that was hanging out. I try to be a fun date regardless of my interest level but I think the Brit caught on towards the end. True to his Continental manners he walked me to my car and chastely kissed me on my cheek. Cheerio, old chap.

He Likes Me... He Likes Me Not...

I recently stopped being one of those girls that came up with hundreds of reasons why guys didn’t call me. Now I just believe guys who like you, call you. Or email, or text message, etc. I also believe guys who like you ask you out. It seems pretty straightforward so this is obviously where I get into trouble.

Take this guy I recently met online. After a few emails we talk on the phone, but I think I’m talking too much, rambling and being uninteresting. I must do something right, because he suggests we get together sometime and I agree that we should. No actual plans are made, though, and our conversation ends when he abruptly says he’s heading to bed.

My gut says, he’s not interested, suggestion to get together without any invite details (when, where, what) is usually a courtesy phrase, like when you run into someone you used to be friends with and on parting say "we should get together sometime". You both nod, knowing you’ll never call each other.

I’m feeling adventurous, though, so as my weekend is winding down on Sunday I call him to see if he’s free for sushi. I leave a voicemail and don’t hear back until a few days later, but he seems friendly and throws out drinks on Friday. Maybe I had it wrong, he does seem interested.

I’m not available on the Friday, though, so I counter with Wednesday. He’s not available and we exchange a few emails that end with me asking whether he wants to pick a date to grab drinks next week. I hear back nothing for ten days (including two weekends). Not interested.

But then out of nowhere, he sends an email saying he hadn’t heard back from me… did I still want to get together? Interested, albeit inaccurate as I had emailed last.

I reply back promptly that yes, I am interested. What did he have in mind? Two days later he responds asking what I was doing over the weekend and that he was thinking Sat or Sun. Now I’m confused. Not interested?

My trusty guy work friend says he might be trying to avoid all the scheduling issues we’ve been experiencing by being the most flexible dude ever. I think this sounds ridiculous, asking someone out on a date should involve coming up with the details. Nevertheless I reply with what I hope sounds positive, saying that Saturday would work and what should we do?

Two days later, mid-Friday, I still haven’t heard back. Not interested, definitely, and this time, I’m talking about me.