Online Dating Guide & Blog

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According to a new Match.com commercial I’ve been seeing lately, 1 in 5 relationships are now started through online dating services. Still, even with that fact, there are a large number of singles who believe that online dating does not work, or at least not for them. With that in mind, I wanted to post a challenge to all of the doubters. I really believe that people who feel that online dating doesn’t work fall into one of [...]

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Thinking of interesting and unique date ideas can be difficult. Sure, you can find some good ideas if you look long enough online but even many of those end up being something less than interesting or unique.

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There are many mistakes that are made on first dates…far more than I will list here. However, I will cover the 10 mistakes that I saw from others while dating online, made myself while dating or have learned about by talking with other singles about online dating. If you are struggling to find second dates I would strongly recommend seriously reviewing this list.

1. Trying to Act Like Someone Else
Many people ask: How should I act on a first date? The [...]

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As I discuss in my online dating guide, I think it’s best to be prepared for the worst when going on a first date. By no means did all of my online first dates go bad (many went great) but there were more than a few that I expected to go well that went horribly. As I’ve suggested, I think the best approach is to tell the person you’ll be meeting that you will only be available for a short [...]

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I was recently talking to a woman who decided to end an online relationship after the first date because her date had complained for much of the dinner. This got me thinking about complaining in general and how as people we are so drawn to doing so. Even when this woman came to me to discuss this bad date, she was doing so to…well…complain!

Because as people we complain so often, I don’t see the activity in itself as a [...]

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In my last post, I discussed ways to break your way into the conversation even if your date doesn’t ask you any questions. Today, I wanted to discuss this same issue but from the other side: remembering to share the conversation.

Sometimes people are simply too excited on a date and the result is that they talk about themselves the entire night. Another thing that happens with online dating is some people, particularly men, will research ways to keep the conversation [...]

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A reader recently wrote in with this frustration: on dates he is able to get conversations going easily but finds most of the women he meets, while willing to answer his questions, ask no questions of their own. They often appear very interested in the conversation but are willing to allow it remain about them. He questioned whether these women, who often seem swept off their feet, are actually interested at all. His dates would also say things like “Gee, [...]

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Is there any recovering from a bad first date? If you know you made a bad first impression or if the date went badly but you are hoping for a second chance, my honest opinion is that the odds aren’t in your favor. This is especially true if your first date was set up through an online dating service or was a blind date. This should obvious considering how important a first impression is and with online dating the first [...]

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One of the most important things to be concerned with on any first date is ensuring things start off the right way. Several studies have suggested that the first moments of interacting with someone are the most important. Most people who have been dating online for a substantial amount of time don’t need a study to tell us this: plenty of us have known within the first few minutes that a first date was going to be the last.

Making sure [...]

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I was discussing online dating with a friend recently and she explained how she has twice ended an online dating relationship with men due to the fact that they didn’t even offer to pay for her on the first date. These dates weren’t anything expensive either, just coffee. These men had also established that they had well paying jobs. I’m surprised that this happened to her twice in a few months so I think this topic is worth covering.

Guys, the [...]

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In a recent article, I discussed how to dress for a first date. However, even when you know what to wear in general, there are times where it’s not clear if a particular outfit is worth wearing. We often second guess our opinion on the outfit and either decided not to wear or we wear it but worry all night long. In both cases, we can end up regretting our decision.

I’ve seen it recommended to upload a photo of yourself [...]

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I recently read a great article that describes some situations that may seem bad on a first date but could actually be a sign that things are going quite well. The article, 6 Bad First Date Signs That Are Actually Good, is worth reading because sometimes we convince ourselves that things have going horribly when they’re actually going fine. As an example, how many of us have gone on a job interview and thought we did a bad job only [...]

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Don’t do this! I was talking about online dating experiences the other day and woman was describing her most recent date. She was explaining why she had no intention of having another date with the man she had met the night before. There were several issues she had taken with the date itself but as we talked I get the feeling this man had ruined his chances in the first few moments of the date. Simply said, he was dressed [...]

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Do You Have A Dating Addiction?
Steve at SeaCoastOnline.com discusses addictions in general and specifically the idea of having a dating addiction. If you date online long enough you will probably run into someone who seems to have a little too many dating stories. You might find yourself wondering, “Exactly how long has this person been dating online?”. My opinion is that dating addictions exist and that online dating can actually encourage this activity. If I’m honest, when I met Kate [...]

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How should you dress when going on your first date? I suspect most of my readers will be meeting through online dating services so my advice will be based assuming you’ll be meeting for the first time.

How Should A Woman Dress on The First Date?
If I’m honest, I don’t feel that I have much to offer ladies on how to dress specifically. As a guy, I’ve always felt that women are far better with style than men. Assuming a [...]

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A post at Slate.com discusses eight ways to tell whether you’re being boring. While the article wasn’t written for online dating specifically, I think the article is very applicable. Some of the tips might even be a little surprising to some, such as why interruption is actually a sign of healthy conversation

I think the article provides very good tips on recognizing if you’re being boring. And the truth is, many times we can’t see that we’re not being very interesting. [...]

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Before discussing some good questions to ask on a first date, I wanted to offer several tips on first date conversations in general.

First, you should ask your questions with a purpose. Specifically, you should be trying to determine if this is someone you would like to continue to spend time with. Don’t just find a bunch of questions on the internet to ask just so you can “fill the silence”. While I will provide examples it’s best if you [...]

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Some Dating Email Dos And Don’ts
Quick tips on CNN provided by the site TheFrisky.com for sending emails and overall I found the advice good. In some ways I was surprised as I find myself shaking my head more often than not when the main stream media dives into the dating advice business. Maybe it made sense since someone else wrote it (although I’m not actually familiar with TheFrisky.com). I will say that number 5, which says you should wait at [...]

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Have you ever been on a first date where from the very beginning your date was rude or angry? I’ve experienced this type of date once when using internet dating sites and have heard several horror stories from friends who have also run into this. From what I have seen, it seems to happen most on blind dates or online dates. So what is exactly going on when someone counts you out before you’ve even said “hello”?

What Creates this Situation?
Part [...]

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Since I started this site a few months ago, I’ve been actively looking for great resources that I could share here. Unfortunately, almost everything I have found online has fallen into one of three categories:

Overly general advice that feels extremely polished and impersonal. For example, the type of advice I would expect to see in a Maxim magazine (but less humorous). I find it hard to put much confidence into something that reads as if a team of writers tried [...]

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