Sleeping With Money: How Much Should You Invest on a First Date?
‘œThe best way to find your perfect match is to meet love halfway.’ ‘“ Author Unknown
One of our straight friends is trying to date online and in her words, ‘œIt’s been a disaster.’ Last Saturday night, she spent five miserable hours on a marathon first date.
‘œFive hours?’ I asked.
She explained they met for a casual dinner, walked around the corner to a gallery event, and then ended up in his truck for a make-out session. The guy was forty-four.
I didn’t know that people still made out in their cars. Apparently they do. Call me old. Or prudish. It’s not that I’m above it’¦ I recall plenty of roadside make out sessions when I first started dating Partner #1 but I was twentysomething and that was classified as frolicsome recreation back then. I haven’t done it since.
Anyway, our poor friend escaped his clutches and so the other night I gave my lecture on Internet dating. I consider myself a seasoned survivor’¦ after all; I was trolling the worldwide web for women long before it was mainstream.
Furthermore, Jeanine and I happen to be a ‘œPlanetOut personals’ success story and people are always surprised to learn this. In between Partner #2 and connecting with Jeanine, I had an active profile (emphasize: active!!) for almost a year.
My friend, Laura, had a profile posted at the same time and we devised this sort of dating buddy system where we compared postings and pictures of our Los Angeles pursuits. Laura (who happens to be skinnier and better looking) got more dates and needed a spreadsheet to keep all the women straight. I had my own system whereby I focused on one woman at a time.
I applied a process to my dating methodology and it went something like this:
- If they don’t have a picture posted require a photo by email.
- Exchange one or two emails ‘“ never any more ‘“ and then make a plan to meet. Women are notorious for falling in lust through words and if you let the emails linger too long a false sense of intimacy develops. After you meet and realize there isn’t any chemistry, it can be a little weird thinking back to all the suggestive stuff that you both wrote.
- Plan a first date – during the late afternoon on a weekend. Make sure it’s nothing more than meeting for a coffee. If you meet and the connection is spectacular ‘“ with conversation lasting for more than a couple of hours ‘“ then it might naturally transition into cocktail hour at the restaurant next door and a bona fide date.
- If it’s a bust, then you can call it a day after 45 minutes and still have a free evening.
Back to our straight friend. I’m not sure why she committed to dinner on a first date. Who wants to make this kind of investment with someone you don’t even know?
I always considered the expense. Dinners could get expensive especially if you’re trying to meet someone new every weekend. Coffee costs a couple of bucks. If the coffee date was a success then I would plan a second date where we’d meet for dinner ‘“ but only if I thought it was worth the money to meet again.
That being said, I did break this rule when I first met Jeanine. We lived 50 miles apart which in LA rush hour miles is like 2 and a half hours. Because it was such a long way to drive, Jeanine suggested that we make it more than just a Starbucks. We met for dinner and three hours later the conversation was still spectacular. Our dinner was less than 100 bucks because we split a meal ‘“ this was Jeanine’s suggestion and something I love and appreciate about her to this day.
She was a keeper and definitely worth the first date investment.
What about you? What are your dating rules? First dates, second dates? Who pays for what? I always enjoy reading your comments below.
Coffee in the mid-afternoon might be a good one. Then you can turn it into dinner if you really hit it off or just say you have dinner plans.
*raises hand about having made out in cars* It’s what happens when you share a dorm room with a couple girls and have nowhere else to do it. Oh the things I’ve done in cars! But I’m liking being married and having our own place. I was also 17-21 for this.
Oh, dear god, you made me laugh when you said your friend had to have a spreadsheet for all the gals she was dating.
I must admit that about a year ago, it got to the point where I went on six days in a row with a different date each day, and then started it all over! For a while, I was balancing upwards of four people at the same time.
Ah, good idea about the afternoon coffee date with potential to extend. I just blew about 8,000 yen (about US$70) on a 24-hour first date. That’s a lot for a humble waiter, hehe. I’ll just have to work a few more hours.
If I knew then what I know now, I would have done the following in my single days:
Always go cheap for online dates. If there’s a next date, not so cheap.
For dating people in your extended network of friends and acquaintences, invest in a date as nice as you can reasonably afford. You’ll want to preserve your reputation in case the date goes bad.
I have gone on hikes/walks. This has been great because you can sit afterward and talk or go get some coffee. They can also bring their dog or kid and let them play while you walk around.
Question: Why did your friend have a make out session if she had to “escape” his clutches? Does making out mean so little that it is preferred to make out than say I am sorry I did not feel any chemistry?
Good story!
The nice thing about a first date that costs a bit of money is that you can learn A LOT about the person and how they relate to money (which, as you know, is pretty important). If a person grumbles about the cost or if they get all fussy about who owes what … you’ve just learned something pretty vital right there.
Mrs. Micah: Good to know I wasn’t alone in my young adult activities.
Vixen: Sounds like you could have used a spreadsheet too!
Alec: Like you I learned from experience… go cheap on the first date.
John: In my single days, all my dates were met online except for the straight, curious girls I befriended at the gym… more fodder for a future Sleeping With Money post: how to justify the expense of a gym membership.
J Dawg: The hike / walk idea is a good suggestion. During a brief man-dating stint I noticed that the motorcycle guys always wanted to take me for a ride… I always thought that was strange because it was pretty hard to get to know someone sitting behind them. Maybe it had more to do with the “you should hold on to me” line that I heard more than once. Re: our friend… well, I guess it was harder for her to speak up.
Reese: Excellent point. Here are two posts that touch on this subject a bit: One by Paula about the picking-up-the-check dance and a guest post from Madame X at My Open Wallet.
Great topic. You probably shouldn’t spend more than 5 or 10 bucks on a first date. – Why invest the cash if you don’t know if you like the person or not?
This is such a fun topic. I remember one day I went on three dates. Didn’t cost much because one was a brunch (he paid) then was coffee (that’s cheap for a date) and the third was a movie at my place (grab a dvd off the shelf).
A spreadsheet is pretty far out though. What about the value of your time in having to track all of that dating? Seriously what is the ROI??
Very fun topic… I know someone (straight) who recently went on a first date that ended up in a car make-out session. When you are in your mid-40s in the suburbs and divorced with kids, I think it’s more common than you’d suspect! I can only remember one automotive make-out in my own history, during a torrid college affair. In NYC, it must be VERY rare, though I hear people do make out in taxis… personally I’m not that much of an exhibitionist!
Back to money, the afternoon coffee date can be good, I’ve done those. But I think if you’ve had a good online rapport, it’s worth taking the plunge and going for drinks or even dinner. But then I am one of these people who’s hungry all the time, and I’d rather endure a longer, more expensive date than starve!