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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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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Dating Website Activity after a First Date

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What is the etiquette for logging into a dating site after a first date? Should I be upset if I see someone logging into a dating site after our date? Alternately, is it impolite for me to log into a dating site after a first date that I’ve gone on?

I see this question most often from the angle of: “We had a great first date but I saw that he/she was active on Match yesterday so I guess ...

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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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When Your First Dates Consistently Fail for One Reason

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A reader recently wrote me with a very unique situation that was leading to multiple unsuccessful first dates.

In many cases, failed first dates can be a mystery: did she not like my personality? Was he not attracted to me? On the other hand, sometimes we know exactly why we are seeing failed dates…we just don’t know how to respond to them.

In this case, my reader knew exactly why he was struggling on the first dates but wasn’t sure how ...

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Asking Out Online Daters Who are Nervous with Online Dating

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A reader wrote in that he was talking with a woman on an online dating service but she was very nervous about actually meeting someone using the service. Here’s his question:

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. The girl has a really nice profile but took a few days to respond to ...

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Thoughts on Dating Confidence and Comfort

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When I first started this site, one of the things that bothered me most about the online dating advice I had been finding was that everything had the same answer: be more confident.

I found this advice very hard to take and I actually gave up on acting confident. I think occasionally I might have been successful at appearing confident but I was consistently successful as not portraying who I really was…the gains weren’t worth the sacrifice.

At any rate, I discussed ...

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Tips for Better Conversations on the First Date

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First date conversations are a tricky thing: we all realize how important they are but sometimes we still don’t prepare while other times we put so much emphasis on having “good” conversations we actually create problems for ourselves.

In one of my very first articles for this site, I had given tips for first date conversations based on what worked well for me. I wanted to touch on the points I made back ...

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