42 Dating Disasters

Going out in a group is absolutely key for meeting people in real life. Here is how I work my group to get the most bang out of it.

• Compose. If you’re looking to meet someone new, group composition can be pretty important. All women with one man… you are the gay friend. Equal parts men and women? You’re all attached, and you may just be a freak (not that this would turn everyone off, but it might be a huge let-down for those it doesn’t). All men is okay, as long as you don’t start dancing together (gay) or are too big of a group (football, or worse, ultimate frisbee team). You’re going for “strong, but not overwhelming”. Note that it is actually easier if not everyone in your group is available. Those people often make excellent wingmen. Even if they don’t, there’s no need to bring your own competition.
• Strut. Be seen as a part of your group. Walk through the place with your entourage in tow. You’re the man. Believe it. Sell it. Make sure everybody knows it. This goes double if you’ve never met or been out with anyone in your group before. If you can convince them, you’ll convince everybody else.
• Mingle. Talk to people on your own, without your “support” nearby. Offer to bring your group into someone else’s group. This works really well if it’s a large group of available women and a small group of men. Also, when you start talking to strangers, don’t hang around too long. Make an impression and move on.
• Follow up. Since your first contact is brief, make sure you go back and talk to the women who seem to share mutual interest. Bonus points if you manage to greet them and all their friends by name when you come back. If you click, then spend some time really talking during the follow up. If not, it won’t be a surprise if you leave within a minute… it’s what you did last time you talked to her, too. Just don’t be surprised if you get the same treatment.
• Close. Closing is really tough in a group environment. I prefer just to get a number and call it a night. There’s plenty of time for a REAL close later.

Have you done better with “the group thing”? Any other tips that have worked for you? Let me know in the comments!

No, this wasn't my teacher this week

Wow. What a week. Since I had only one date this week, I thought I should share some things that I learned this week. I have learned a lot about how unreliable people can be, especially certain kinds of people. I learned (confirmed?) that women are definitely just as superficial as men when it comes to profile pictures. I was also propositioned this week, and it was not subtle… or good.

At the beginning of this week, I had 3 dates scheduled. I had a short-term opportunity with someone I met offline, so I pushed one of these 3 to the next week. So, technically, I suppose I had 4 dates scheduled this week. Only one happened. One was my choice to move to next week. Two canceled at the last minute. That leaves me at 50% for the week. On the plus side, I have not been stood up yet. It takes a lot of energy to talk with women and to arrange these meet-ups, at least the way I do it. It’s at least a few emails back-and-forth, a conversation or two on the phone, then we finally get a chance to meet. Multiply this by 4 and you have some idea of how exhausted I am, mentally and emotionally, from this week.

Women are just as superficial as men, in case you didn’t already know this. I was getting only occasional action from a particular online dating site… until I updated my profile picture. Choosing a profile picture is a complex process, I’ve found. I have a theory that different pictures work better on different sites. But for now, I have updated my profile everywhere with the new picture. Time will tell which technique works best.

Chasing women with a “boyfriend” is pretty interesting, but in my experience so far, not very fulfilling. These women tend to be younger, and they tend to take that level of relationship pretty seriously. Of course, they each gave me their numbers, so I made the assumption that they didn’t take them too seriously. The problem may be that they have lots of time to evaluate how serious their relationships are.

Getting propositioned is way less fun than you might think. Even though I like the idea, the reality is just not that hot. What should happen is that physical attraction develops and then something just happens. Having someone suggest it is just weird. Considering this has been a fantasy of mine for a while, I was disappointed that it was such a let-down. I had to escape from this one.

I'm too old for this shiiiiiiiiit

I don’t think I’m “old”, by the way. But I accomplished stuff in my twenties that most people are just getting to in their thirties. So, I really mean “I’m too experienced for this shit,” but it’s not as catchy as Danny Glover’s famous line from the entire Lethal Weapon franchise.

I am a moderately successful, driven, well-educated, well-paid guy. And when I say “moderately successful”, what I really mean to say is that I live in a nice, big house with hardwood floors and a fireplace in a really great neighborhood. And I drive a really nice car… one that people always turn to look at. But, I’m not commuting by helicopter into the nearest metropolis, and my nice car is not a Ferrari. It’s not like I’m loaded, but I make money and I like to spend it sometimes. I’ve started companies and gotten funding for them. Also, my son is going to make your daughters cry some day because he’s smart, funny, caring, athletic, and he even dresses well. He intends to go to a great school, and I intend to get him there. I guess my point is that for some portion of women out there, I might be considered a “catch”.

So, if you’re looking for a professional, established, successful man like myself, here are some tips:

• Don’t blow me off. Ever. If you tell me you’re going to call, call. If you tell me to call, pick up the phone. If you say you’ll email me by Saturday, then unless there is a cataclysmic natural disaster, there better be an email in my inbox by Saturday. This is just common courtesy. Professional guys pick up on this right away. Doing what you say will separate you from the pack!
• Listen as much as you talk. I’ll try to do this for you, too. I will guide the conversation toward something interesting to you (or, better yet, both of us). Really, I love hearing your voice almost as much as you do, but I’m really not looking for someone who thinks life is all about her. Yeah, I know it’s your life, and you’re trying to figure out if I deserve to be a part of it. But, you need to realize it’s my life, too, and I’m doing the same thing. Maybe it’s just me, but I’d like to participate in our conversations. Otherwise, how will you know how smart and witty I am?
• Go ahead, play the “game”; but know the limits. I know what’s going on, and so should you. A little back and forth can be fun, building a little mystery and keeping my interest. But take it too far, and that will just be too much. To use a fishing analogy, your line will snap. Likewise, if you’re not interested anymore, that’s fine. Just cut me loose. The time I’m spending talking, emailing, or meeting with you could also be spent with my son. I don’t take that lightly!
• Offer to pay; at least your part. I won’t accept, so don’t worry. But offering to pay means that you’re at least capable of supporting your own habits and you’re probably not just using me to get free food and drinks. Do NOT argue with me about me paying. Here’s a script for you: You: “How much is my part?” Me: “I’ve got this one.” You: “Are you sure? It’s okay for me to pay… it is 2009!” Me: “No, but thanks! Hey, I think you just got hotter!” Okay, I probably won’t say that last part out loud unless I’ve had a lot to drink. Bonus points to women who offer to pay next time!

Good luck, and let me know if these tips work for you!

Pimp... player... the debate goes on

Have you heard the one about “half your age, plus seven”? I’m pretty sure it’s for extra-marital affairs, but I’ve never really dated anyone significantly younger than me. You know where I’m going with this, right? What an opportunity! I’m often told that I look younger than I am, and I’m certainly capable of acting younger (follow my Twitter feed for up-to-the minute accounts!).

So, I’m 30-something, which means that by the formula, the youngest person I should date is between 30 / 2 + 7 = 22 and 40 / 2 + 7 = 27. I won’t bother telling you exactly where I am in this range, but I am very fortunate to have friends in this age range. Since my separation, I’ve been spending a lot of time with them, but I’ve been relying totally on online dating for actual “dates”. Tip #1: This is totally the way to succeed with a younger crowd. You see, a younger crowd just doesn’t think like a 30-something. They have different personal needs and they tend to make a big deal out of, frankly, stupid shit. I’ll tell you what, youngsters, you spend more than 10 years with someone, make them a part of your life, have them become someone you feel is as close to you as a blood relative, have kids with them, build a household, hell, a whole life together, then have it all come apart. Then tell me how important it is that your boyfriend of a couple years is a control freak and won’t let you have a good time. I do have to say this: They make me feel wise and smart. Your boyfriend bothering you? Kick him to the curb, “girlfriend” (do they still talk like that?). You chasing a guy who’s ignoring you for the really young chick who won’t give it up at the end of the night anyway? Get some perspective! He’ll get what he deserves. Just sayin’.

There is a great upside to this age group, though, and it’s not just that generally speaking they look better than people my own age (there are definitely exceptions to this, and you know who you are! But if you’re a woman and you’re 30 and you’ve spent 20 of those years squinting into the sun, you know that, too). 20-something people are young. They act young, and they pull me out of my comfort zone. They make me feel young when I’m around them. And their needs are sometimes simple. They just want to buy that first condo/townhouse and move away from their roomates. They are just starting out in this world, and I’m so happy to be able to share everything I’ve learned over the years to be able to help them out… whether they are just friends or potential dates.

And this brings me to the real point. I think it’s a total waste to try to act their age to try to get along with them. Recently I was talking with “Veronica”, and I said something really insightful based on my extra years of experience. It was one of those moments when you feel a tangible change in the relationship; when attraction just went up a notch or two. Frankly, I just wasn’t smart enough to earn those points in my twenties. So, when you’re at the bar or on the dance floor, don’t break out your 80s dance moves (resist that urge! I mean it!). But don’t hide your wisdom, knowledge, and experience, because with the right person, they are a huge asset.