Ahh, the plight of single men. If we wish to consort with the fairer sex, it’s up to us to approach women, charm them, ask them out, take them out, pay for the entertainment, go for the kiss, try to get to the next base — and risk rejection at every step. Every time you’re on a date, a cop might as well come up to you and say, “You have the right to screw up. Everything you say can and will be used against you in a court of public opinion of your date’s girlfriends.” You should probably avoid girls named Miranda.
At the same time, you have agency — you get to ask her out, instead of having to wait for the phone to ring. This is a good deal. With a little bit of caution and foresight, you can avoid these dating pitfalls and instead have a lot more fun and success in your love life. Here’s what to watch out for.
1. The postponed response, or the Almost Yes.
You call her up on Monday to ask her out for Friday night. She says, “That sounds great — let’s do it! Except there’s this one thing at work I may have to go to that night, and I won’t know until Wednesday if I’m free Friday night. Can I call you back on Wednesday or Thursday to let you know?”
Ooh. This has happened to many a man many a time. And if she’s some elusive hottie you’re really into, it may seem like you’ve hit the jackpot. She said yes, right?
Wrong. She said maybe. Which basically means you do not have a date for Friday night. Better start looking elsewhere, buddy.
One of the fundamental principles of The Tao of Dating is that fulfillment is a feeling, not a person. You do not necessarily want her for your Friday night. What you really want is pleasant company. And there are thousands upon millions of women who can provide that for you.
So resist the temptation to accept the Almost Yes. Settle for nothing less than an absolute, firm “Of course I’m coming.”
Your goal is to have a date for Friday night. If you wait till Wednesday or Thursday and get a ‘no’, you’re left holding the bag with diminished chances of getting a date. You need your lead time. So give her a deadline.
So if you really want to give this particular girl a chance to come with you, say something like, “Wow, that sounds great. Now I really want to go to this [concert/event], and if you can’t make it, I totally understand. If you can give me a firm yes by Tuesday 5pm, let’s do it. And if I don’t hear from you by then, I’ll just assume the timing didn’t work out for you and we’ll get together some other time.”
Deadlines are great for two reasons. First, they give people a reason to take action. Hell, if it weren’t for deadlines, I’d still be working on my college thesis. Second, they free you up and give you the initiative. Once it’s 5.15pm on Tuesday, you have an answer. This is better than your waiting by the phone being at the mercy of the caprices of someone with an excess of X chromosomes.
2. “Can I bring a friend?”
She’s already said yes to the date and she’s coming. Sweet! But a few hours before the appointed time, she calls and says, “Is it okay if I bring a friend?”
This instantly puts you in a no-win situation. If you say ‘yes’, then you no longer have a one-on-one date but an outing with friends — the dynamic has changed significantly. If you say ‘no’, you sound like a jerk. (Of course, we’re assuming here that the friend is a girl. If it’s a guy, excuse yourself politely, make other plans, and don’t call her again.)
Here are two possible ways to handle the situation:
a) Ask her right back: “What do you think?” She’s already not 100% sure of the situation, otherwise she would not have asked you about the friend. This gives her a chance to talk herself out of it.
b) Tell her, “If you want to go out with your friend, that’s totally fine, and you should go with her. However, I invited you specifically so we could spend time together. So if you want that, you should just come with me.” Once again, this puts the ball in her court.
3. The Lost Message.
You send her an email, text message or voicemail to ask her out or to confirm the date. You don’t get an answer back. You wait and wait, caught between the Scylla of not wanting to contact her again and look desperate and the Charybdis of still needing an answer back because Friday night is coming up and your window of opportunity is shrinking fast.
You either don’t get a response back in time, or she says “my phone died got crushed under a car doesn’t deliver voicemails I don’t check that email account that often your email went to my spam folder I was in the desert with no internet access for a week” or any other number of plausible explanations.
Once again, remember that your goal is to have company on a Friday night. To that end, here are two solutions:
a) Use backup communication and add a deadline. In medicine, using multiple therapies to corner an infection is common practice. You’re adding redundancy, so if one modality fails, you still have two other ones. Use the same technique here: send her text (or voicemail) and email simultaneously. For example, invite via email, then send a text saying ‘check your email’. Even if her phone fell in the pool, she’s bound to get one of the messages. Invitations are best done in real time, so I recommend calling first.
Then put a deadline on her response: “If you could get back to me by Tuesday night, that would be great. If I don’t hear from you, I’ll just assume the timing doesn’t work for you.” That way, whether or not she responds, you’ll have an answer by Tuesday night and can take appropriate action.
b) Ask out more than one person at a time. Again, your goal is good company. So invite several women and set up the date with the person who commits first (which may be different from the person who responds first). If you’re not the guy who has multiple options for a Friday night, then go out and meet more women so you become that guy. The more options you have, the more power you have and the less needy you act.
4. Paying for the bill.
Especially in the early phases of courtship, a lot of guys trip up over this piece of protocol, derailing potentially fruitful relationships. Here are the guidelines I recommend:
If you invited her, you pay for everything, no questions asked.
If she offers to pay her way, politely decline her offer, and make a mental note that her parents raised her well.
If it was a mutual decision to get together, split the check. If she invited you, offer to pay your way but accept if she insists on picking up the check. The simple way to do this is to ask “How much do I owe you?” when the check comes, and notice her response.
There are certain things you can do to prevent these complicated situations from arising in the first place:
a) Make the early dates more about the company than about spending money. Lavish meals at expensive restaurants, pricey concerts and impromptu trips to Paris on your Gulfstream are out. Coffee or drinks at a local hangout or any number of fun, free events listed in your local paper are a much better bet.
b) Take the ‘my treat or yours’ question completely out of the equation by either getting there early and getting your own drink first, or alternating (“I get this round, you get the next one”).
5. The Early Leave.
You set up the date for 7.30 on Friday night. She says yes. She shows up! Score. You’re having a great time, sitting on the couch, sipping a glass of wine, gazing into her eyes meaningfully while casually twirling her long tresses.
That’s when she looks down at her Cartier wristwatch and says, “Oh no! It’s 9.30. I have to go catch my friend’s show at the Hotel Café. Can you walk me to my car?”
Have to go? At 9.30? Walk me to my car? What the hell just happened here? Women do this kind of thing?
You just got blindsided by the Early Leave, buddy. It’s okay — happens to the best of us. The Early Leave is a little bit like obesity: once it’s happened, it’s too late to do much about it. Only prevention works — a little bit of good dating hygiene takes care of it.
This is what you do: at the time that you ask her out, after she says yes, you ask: “Do you have any other plans for that evening?” Most of the time, she will giggle and say of course not, silly — I just make a date with you. But you’ve done your part to prevent the unexpected. And if she excuses herself from the date early, you’ll know it’s because she’s not having fun with you, not because she’s going to another party.
6. Being stood up.
There’s not a whole lot you can do about this once it’s happened. Again, good dating hygiene can give you some prevention:
a) Confirm the date the night before and the day of the date. Just make it a routine part of your practice.
b) Set a deadline for yourself such that if she is X minutes late, you are free to move on. 30 minutes is about right.
c) Have fun. You’re already dressed up and out on the town, so enjoy yourself. Never take it personally. Living well is always the best revenge.
On the off chance that she really did have a legitimate excuse for standing you up, the next day, send a message asking non-judgmentally what happened : “Is everything okay? Give me a call.” If it was all a big mistake and she does want to see you again, she will call you, at which point you can figure out how she can make it up to you.” And if you don’t get a response, chalk it up to experience and go along your merry way.