I thought this would be an interesting question, especially since it’s not something you generally have much control over.
The best time to start dating: February 15th. Valentine’s Day is behind you, and the holidays are ten months away! 
Unless you live someplace where the government issues you girlfriends, it certainly is something you can control.
I would say before the holidays is bad because you have to get gifts.
My friend, on the other hand, tends to prefer being free during the summers and then getting a girlfriend for the winter.
Good Gracious, mercenary kinda guys eh? The best/worst times depend upon whether or not you “have” to get gifts?
Anyway, summer imho, because the weather is so much nicer, you can do things that are more active and fun.
My guess is before a major gift-giving holiday. You’ve just started dating someone, you’re not sure if you should get them anything, if so, what do you get them, but what if they aren’t expecting anything, what if they feel pressured if you get them something, etc.
November through mid-February are the worst times, in my opinions. Not because of the gift-giving, so much, but because of the awkwardness involved. If you’ve been dating exclusively for a few weeks, do you do the family Thanksgiving thing? By the time you get to Christmas, it’s even worse. Then there is the gift exchange. Do you buy a piece of glitzy jewelry? A sweater? A condo?
February is self-explanatory of course.
Gimme May romance. By the time you get to the holiday stuff it should be fairly straightforward and obvious.
No, it’s not that we’re mercenary–it’s not the expense that’s at issue. It’s just that if you’re in the early stages of a relationship when a traditional gift-giving occasion arrives, the issue of gifts greatly complicates matters. Too much of a gift, too soon, might be inappropriate when the man and woman are still in evaluation stages, so to speak, of the relationship. But no gift, or too small a gift, or a gift without the correct implications, might also lead to disappointment and ill-will.
It’s just another one of the ways we can screw up, and therefore best avoided.
I would say right before Valentine’s Day. I started dating Ardred February 2nd. We went out for a few weeks and then had a nice romantic dinner for Valentine’s day. Also, you know well enough by the time the major family holidays roll around if you’re going to want to introduce them to the extended family.
Well, my personal answer is “right before the time of year when one of you has to go live 1000 miles away.” (i.e. late summer, for anyone in college or grad school who’s starting up with someone who doesn’t live near their place of education.) You don’t get to see each other, and you’re still unclear on the gift-giving thing and the going-to-see-the-parents thing when it gets to be holiday time.
But for people in general, I agree with those who’ve said right before the holidays, and for the same reasons. Especially if weren’t good friends before the relationship started.
I’m going with mid-February to early-March. I had more than a few lengthy relationships (including the one with my wife) that began during this period of time at different points in my life.
To clarify, I’m talking about the worst time to start dating, not the best.
I’ll go with after right after Thanksgiving. There are no expectations for Christmas, such as meeting family members or breaking the bank on gifts. But it’s a fun time of the year; a lot of parties, a feative mood, and then New Years Eve seems extra special. If you’re still together on Valentines Day, it makes that sillly day fun because it’s relationship is still new. then if it’s still going the next Christmas, it becomes the couples first “real” Christmas together.
Oh, I just reread the OP title. My first post was the best time. There is no worst time.
I agree with those who said that the holidays can be awkward. You never know if you should get the person something or not. Also, I’m not sure about anyone else, but I’m usually with my family a LOT during the holidays, and if you start dating someone during the holidays, you run into not only, “Do I give them a gift,” but “Should I invite them over for the holiday?” If you do invite them over, maybe it’ll seem like your relationship is more serious than it is. Maybe you’ll (general you) scare the person off by seeming to get too serious too fast, or maybe they’ll think you’re more serious than you actually are and start assuming a more serious commitment than you’d like to make. Very tricky. Jeez, I’m glad I’m married.
Drachillix and I started dating in early November and meeting his family for Thanksgiving went a long way in my seeing him as a keeper. How could you not fall in love with a man whose grandmother loves him so much? He took me to his company Christmas party (at a nice restaurant) and I was impressed at how valued he seemed by his bosses.
If you are seeking a mate, I see the holidays as a great time to fall in love. If you’re casually dating, not wanting anyone seriously in your life, incorporating your new flame into your set routine would be stressful. The worst time to start seriously dating someone would be when you had a million other committments and not a strong desire to put this new person’s needs/expectations before your own.
Ah, but when one’s birthday is in March…
Any time during your senior year of college… sigh
For worst time, I would actually go with anytime your future plans are very up-in-the-air, like when you’re jockeying for a promotion or transfer with the company, you think you’d like to live somewhere warmer, etc. When you can see ahead into the future a few years, that seems like the best time.
But then again, speaking as a relative youngster, I’ve never had a period of life where the next few years seem constant or predictable. I imagine it would almost make things TOO easy.
I think I agree with this as the best time to start dating. I recently connected with someone via an online site: we met for the first time yesterday and seemed to really click. We might be going out Wednesday night (though he’s supposed to call me tonight to talk about it, and it’s after 9:30pm and the phone hasn’t rung yet :dubious: ), and if that goes well I could see this becoming a dating thing. And I’m glad that it’s happening now, because no way is there any expectation of Christmas gifts or of meeting any family members over the holidays, or anything like that – but, as kevja says, NYE might be a little more special than usual. And if this continues for another month, I might just be able to ask him to my office holiday party (which for some asinine reason is being held in late January), etc.
I take it back: this is a horrible time to start seeing someone, because now he’s all busy with his daughter and his family (who is in town to see his daughter for Christmas) and I haven’t heard from him in almost a week and I’m starting to think that with both of our holiday obligations I might not get to see him again before the new year and I’M HORNY, DAMMIT!!! :mad:
We started seeing each other seriously in late January. On Valentine’s day, I got her a cute stuffed puppy. I handed it to her. She smiled tentatively. Then, she burst into sobs. Turns out it looked just like her childhood dog who had died a couple years before. :smack:
Fortunately, she married me anyway.
–Cliffy