Avoid Late Night Emails: Good Idea or Over-Thinking Things?

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It’s a situation many of us have been in: you decide to check your online dating account when heading to bed and before you know it, it’s 2AM and you’re considering sending an email to someone new. But would the timing of the email send the wrong message? Here’s how one reader puts things:

Just a random thought: Sitting here trying to write a message to a girl on a dating site and I’ve realised it’s gone 3 A.M., which is ...

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Being Aggressive About Meeting without Scaring Her Away

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If you’ve read my dating guide, you know I’m for meeting quickly when using online dating. However, there are times where the approach of trying to meet quickly may not go over well with who you are communicating with. Here’s one example from a reader:

I’ve been emailing a girl on Match.com for a couple of weeks now, and I’m struggling to work out where I stand, and how best to develop the email conversation into a real date. I ...

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Responding to Contact from “Fake” Profiles

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A reader recently contacted me with the following situation:

Just getting my feet beneath me with online dating. What comes clear very fast is that there is a LOT of faking going on, lots of winks from “cardboard” profiles with boilerplate language and a GQ profile photo. Can you discuss how to navigate this and even how to understand it — I don’t get the whole purpose, aside from them maybe asking for money, which of course I would never fall ...

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Renewed Interest in a Guy after You’ve Rejected Him

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Online dating can introduce some interesting situations and one that I’ve discussed with some women is the issue of becoming interested in a man after you’ve rejected him.

I suppose that this sounds odd to some people, but there are factors with online dating that create this situation. There can be many reasons, but here are a few reasons why a woman may at one point turn a man down but then later find her interest in him growing:

  • When women ...
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Handling a Long Delay Before the First Date

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As frequent readers know, I’m a big advocate of meeting early when using online dating. I won’t get into all the details here but if you’re interested on why I feel this way you can check out my article on the first date or my post titled With Online Dating, Meeting Matter.

So I recommend meeting early…but what should you do if you communicate with someone that seems great but they are unable to meet in the short-term? Here’s ...

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Match.com Baby

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As many reader’s here know, I met my wife using the dating service Match.com. We’ve been married for 5 years now and are entering the next phase of our family: expecting our first child.

We decided to have some fun with finding out the sex of our baby by having a gender reveal party. If you’ve not heard of this it goes something like this:

  1. My wife and I went to the doctor’s office and had a sonogram done that reveals ...
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Height and Education Requirements in Online Dating

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A reader recently contacted me with the following questions:

I had a couple questions I was hoping you could help me with. I am self-employed, make a comfortable living, and I am about 5’8-5’9 in height. I have run into a lot of profiles where the woman has stated that her date needs to have a bachelor’s degree or be taller than I am. Do you think it is still worth it for me to contact them or should I just ...

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Trying Online Dating after the Death of a Spouse

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A reader recently contacted me about determining the “right” time to date again after her husband had died. Specifically, she was looking to know if she should give it a try or if that would be a mistake. Here is the basic idea from her email:

My husband passed away some time ago and I’m starting to consider dating again but I’m not sure if online dating would right for me. I’m not sure if I’m ready. Can I sign up ...

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Online Marital Status After a Very Short Marriage

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I received an email some time ago that actually hit pretty close to home in regards to my experience with online dating: How should I handle listing my marital status when I was divorced after a very short marriage? Especially when the divorce was caused by the other person cheating? Here is the email that was sent to me (I’ve changed some details to protect her identity):

A few years ago, my very short marriage of about a year broke down ...

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Issues with Older Men Contacting Younger Women

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With some regularity, I hear women complain that men older than their desired age range are contacting them when dating online. According to some of the women who write me, the majority of the men contacting them are outside their desired range and they find this very frustrating.

I wanted to talk a little bit about this, first by looking at an email from a man wondering how he should handle this type of situation:

Last week I turned 63 and coincidently ...

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Should Online Dating Come Naturally?

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I recently had a reader contact me to let me know that he was giving up on trying to use online dating. He listed several things that bothered him but a big part of his argument was this:

Online dating should come naturally and if it doesn’t come naturally for me, then I guess I shouldn’t be using it. Online dating is hard and that’s a problem…right?

I think the idea that online dating should come easy is a common misperception. ...

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Did You Make a Resolution to Use Online Dating?

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In my last article I talked about taking your resolution seriously if you are resolving to date online. If you’ve not read that article already, I’d encourage you do do so.

I have a free online dating guide that you can download but I realize not everyone wants a full book on dating to read. Because of that, I wanted to list of a few of my articles that I think are most helpful to someone ...

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