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. It’s easy to see why people would think online dating would be easy: log into a website with thousands of singles looking to date – how hard could it be? The thing is, there’s a lot that isn’t natural to us about online dating.

1. Does writing positively about yourself (without bragging) come naturally to you?
2. Does pursuing strangers to convince them to go on a date you come naturally?
3. Do blind dates feel natural?

If you can answer all those questions with a confident “Yes”, then it would make sense to me that online dating would come naturally to you. If, however, you’re like me and you answer “No” to those questions, then I have to ask: why would you think online dating would feel natural?

Online Dating Can Be Hard Work
I think at the heart of the issue is the fact that for most of us online dating is going to be hard work. I devote a fair portion of my dating guide trying to convince people to take the amount of effort that online dating will require seriously. Far too often I find myself talking to people who didn’t take the effort seriously and then turn around and see themselves as a failure when they’re not in a relationship after a few months.

That said, from my personal experience I can see that the hard work and frustration was worth it. Was it fun dating online for six months and only ending up with one or two first dates? Was it fun having women write me back to explain in great detail exactly why they would never date me? Was it fun to see women I thought I’d made a connection with simply disappear? Of course not. But in the end, the effort was still worth it.

Often success with online dating comes down to how persistent you are. The annoyances found in online dating can drive many singles away from it. So if you’re new to online dating or just feel like you’re failing because it’s not coming naturally, remember: online dating isn’t easy for most of us. If it did come easy, then a website like this wouldn’t even need to exist. Instead, it can be hard work…so cut yourself some slack and try to stay persistent. The reward is well worth all the headaches it requires.

Related posts:

1. Is Online Dating Worth It?
2. Group Dating: Another Way To Date Online
3. Frustrated or Confused With Online Dating?

At a company Christmas party several years ago we were in a group of at least 6 people (perhaps more, my memory fails me) and everyone was talking about how they met. When it came to my wife and I, we weren’t embarrassed: we simply stated that we met on Match.com.

My story highlights why some people are embarrassed to admit they met online and a reader wrote to me discussing exactly that:

My boyfriend and I met on an online dating site but he lies to his friends and family about how we met. I asked him why and he responded with its embarrassing and its none of their business that he was on an online dating site to meet people. We have been dating for 3 months and things seem to be going really well but I don’t know how to take this and I don’t understand why he doesn’t just tell the truth. I refused to lie about it and I told him I don’t want him lying about it but he doesn’t think it is a big deal. I feel like if he is going to lie about that, what else would he lie about? Am I thinking too much into this and overreacting?

Is it Okay if They Want to Lie?

So, my reader is basically saying: I don’t want to lie and I feel like him lying about this might mean he will lie about other things. I can see why she might feel this way but, at the same time, lots of people lie about this. There’s still a good deal of embarrassment about dating online for some people (her boyfriend being the current example).

That being said, I think it’s a pretty small issue to have compared to a lot of the emails I get. I’m not saying it’s a good issue to have, but things could definitely be worse! If you find yourself in this situation with the person you’re dating, in the short-term I would encourage you to be willing to work through the issue.

I definitely feel that at some point honesty should be achieved and you should be able to talk about how you really met. However, some people really, really care about what other people think and I wouldn’t encourage minimizing someone else’s emotions. I also don’t see this issue as some type of measure for how honest a person is. When people are embarrassed by something, they tend to be very quick to lie about it…even extremely honest people. With that in mind, I would use their response to something they see as embarrassing as an overall measure of their honesty.

So early on, I wouldn’t say you should try to force them to admit how you met. Apply some pressure? Sure, that’s fine. But if you go around telling everyone you met online just to prove to him/her that doing so is fine, you may just create resentment or damage the relationship.

That said, once things become more serious and it turns into a long-term relationship, I then feel that people have to come to terms with being honest to people on how you met! At this point, who cares what other people think? You’ve found someone great! Be willing to be honest about it! And not just for yourself: if you admit you found success online you can encourage others to do the same.

Really, in the long-term there are only two solutions:

1. Both people agree to lie about how they met for the rest of their lives

2. Honesty

My wife and I are honest about how we met and, yes, sometimes it still seems to make some people feel awkward. But over the years, that has been happening less and less often and now most often people are simply interested in how it works (especially singles!). Plus, we have each other: when someone is awkward about it we can just look at each other and laugh!

Related posts:

1. Be Aware of What You Reveal as You Communicate Online
2. Men That Go Beyond One Email Attempt in Online Dating
3. Online Dating Success! Now What?

In that article, I discussed how the reader had a theory that contacting later could be beneficial because she may be more able to respond at that time. This wasn’t something that I had considered in my original article on contacting a second time (but an idea I liked).

So while it sounds like a good idea that a man would pursue a woman beyond one email, I’m looking to get some reader feedback from women on what they think of this approach. My concern is that what works well in the real world might just end up being creepy in the online world.

Some Questions for the Ladies

With that in mind, I’m curious if any women could comment on the following questions:

1. Does the enjoyment of “being pursued” translate to online dating? Or are real life and online dating simply too different?
   
   

2. If additional pursuit is acceptable, where do you draw the line for number of attempts? For example, the same guy emailing you every two weeks for a year, that would be annoying.
   
   
3. Do you feel the man should wait an extended time before contacting you again? Obviously if he’s contacting you every day that’s bad but should he wait weeks to try again? Months? Never?
   
   
4. Is there a point you would let the man know you’re not interested? Obviously no one expects women to respond to every email with “No Thanks” (and I’d honestly encourage you to not do that) but if a man were to contact you more than once would that encourage you to state that you’re not interested?
   
   
5. Have you ever ended up dating a man that repeatedly pursued you online? If not, have you ever found yourself at least having conversations with them after a second email where you had not responded to their first email?

When answering those questions let’s assume:

• He’s pleasant. He writes you real emails (not form emails) and may even make light of the fact that he’s contacting you again.

• He’s within the requirements you describe in your profile. This doesn’t mean you find him attractive or interesting necessarily, but he’s not ignoring what you’ve stated that you’re looking for.

Obviously, every woman can be different in her views on this so I’m not really looking for a “right” answer for guys. I’m just looking for some honest feedback that guys could take into account as they try to pursue some women beyond a single email. I’ve been recommending that men be willing to make additional attempts and would be interested to see what women using online dating think of this.

Related posts:

1. Online Dating Email Tips: More on First Email Length
2. Should I Email Again If My First Gets No Response?
3. Dealing with Email Responses That Show Little Interest

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 this topic in one of my very first posts which I originally titled The Importance of Comfort but have since decided to rename Dating Confidence vs. Dating Comfort.

The last three months of my online dating experience was exciting and fun and never did this shy guy have to pretend to be something he wasn’t. Since it’s been years since I first wrote this article, I just wanted to point it out to any new readers as I still believe what I argued all those years ago. I’ve been giving advice several years now but I still prefer real comfort over fake confidence. I hope it’s helpful!

Related posts:

1. Online Dating Success Story: Post-Wedding Thoughts
2. 5 Tips on Re-Entering the Dating Scene
3. Thoughts on Online Dating Success Rates

I understand the need to be safe but I really dislike this suggestion. Mostly because I had a woman bring a friend on a first date with me and it really hurt the odds of having another date (there wasn’t one). Admittedly, I found her approach as annoying as her actions…so I guess a full story is in order.

Photo by Desiree N Williams

I Hope You Don’t Mind but…

As I discuss in my online dating guide, there were several periods of my online dating life and this date came just as I was beginning to enjoy online dating. I was doing my very best to remain open about all dating opportunities but I was also becoming more assertive in not endlessly chasing one woman or anything else that I felt was wasting my time.

At any rate, I had been talking to this girl (who we’ll call “D”) for about two weeks and we had decided to meet at the Pittsburgh’s Carnegie Museum of Art. At this point, I thought everything was fine: she’d given no indication that she was nervous about meeting someone from the internet and as far as I knew she was looking forward to meeting as much as I was.

From Bad to Worse

I arrived at the museum a bit early to buy our tickets and around that time I received a phone call: she was about 10 minutes away and she was coming with a friend.

This surprised me and honestly I felt let down: things were suddenly feeling much less like a date. At this point I didn’t even have a guess as to why she would want to do this (as a guy safety isn’t something that is always going through your mind). Still, I was trying to change my approach and be more open so I decided to try to make the best of it so I bought a third ticket (make a good first impression with her friends, right?)

Photo by Desiree N Williams

When they arrived I suddenly realized meeting two women on a first date was even more awkward than I thought it would be. Little did I know that things would only continue down the path of awkwardness even further as the date moved forward. Specifically, there were large portions of the date where I didn’t even feel like I was on it: D and her friend were giggling at this or discussing that while I tried to work my way into the conversation.

Honestly at this point I’d say my interest level was just about dead. I was very disappointed because I had gone in with high hopes and I suddenly found myself going from excited to surprised to frustrated to feeling like I was just wasting my time. I guess some of this must have shown because near the end of museum it was obvious that D was trying to put an effort into actually going on a date with me.

Now She’s Interested

At the end of the night her friend drove herself home and I agreed to take D home. Here I finally had one-on-one time with my date and she even dropped hints that she was interested in seeing me again…but I had already decided to move on at this point.

In the past, when I was having trouble getting dates, I probably would have dealt with this and continued dating her. However, I felt like this wasn’t the last “game” we’d be playing and I had no interest in wasting my time when there were dating services full of women I could contact.

Honestly to this day I still have no idea why D thought bringing her friend would be a good idea. She never showed signs of nervousness or concerns for safety and I would say she was bubbly and out-going. Your guess is as good as mine.

If You’re Going to Bring a Friend on a First Date

If you’re thinking of bringing a friend on a first date…first, I recommend against it. There are other ways of making your first dates safe such as:

• drive separately
• meeting in the day at a public place
• schedule to only meet for 30 minutes
• let a friend know where you are and have them contact you at the time that your date should be over.

Photo by Allie_Caulfield

1. Make Your Intentions Clear Early

From the very start you need to be preparing the guy you’re meeting that you take extra care on first dates. Don’t call him on your way there and mention that you’re bringing a friend! Make sure he knows that you’re nervous about dating online or safety or whatever and let him know that you’d like to bring a friend on a first date. Just springing it on someone is likely to end up with them having the same reaction as me

2. Suggest a Double Date

It would be even better if you were to encourage him to bring a friend as well. This could change an awkward situation into a fun one where you and your date get to play matchmaker for yourself and possibly a friend as well. Had D suggested this I would have thought it was a creative and fun idea and would have been happy to bring a friend.

3. Don’t Forget Who You Are on the Date With

I think I might have been able to get past the fact that my date with D had 3 wheels…if I hadn’t of ended up being the third wheel. I actually thought to myself “I hope her friend doesn’t get bored while D and I talk” before they had arrived. Oh, I couldn’t have been more wrong on that one! Just keep in mind that you should be on a date, not hanging out with a girlfriend.

4. Plan with Your Friend for Her to Make an Early Exit

You may find yourself on a date where it turns out that the guy isn’t a psychotic killer who is executing an elaborate plan to get you down to down to the local Starbucks. If that’s the case (and it will almost always be the case) why not plan with your friend to have her leave early when everything looks fine?

Again, I think bringing a friend on a first date is overkill. To me, driving separately to meet at a public coffee shop at 5PM and leaving after 30 minutes is safe. If you’re really nervous, why not opt for that approach? If you can’t resist bringing a friend, at least consider my experience and consider taking some of the suggestions above.

Related posts:

1. Are You Making These 10 First Date Mistakes?
2. 5 Signs to Commit to Date One Person with Online Dating
3. Using Online Dating Advice Intelligently

Photo by Peter Clark

How I Was Stood Up

At the time, I was well into my really-enjoying-online-dating-and-having-success phase. I had been talking through email with a girl that I will refer to as Cathy who seemed very sweet and was attractive. However, from the very start she expressed worries with dating online. It took many attempts and two months before she would agree to go on a first date and even then she seemed nervous.

The day of our first date arrived but Cathy never did. This made me very angry because we had been talking for so long I had thought we were something of friends at this point.

I contacted her again expressing my disappointment and she gave me some excuses. I told her I thought she was lying and that she was just scared but I still wanted to meet her if she would promise to show up. Surprisingly, she didn’t deny any of this and agreed to meet me again.

Cathy did show for the next date and it was a nice date. We walked around and then had a coffee together. Honestly, even though I had been stood up the previous date, I had a nice time and could even see myself going on more dates with her.

However, the next night I ended up meeting the woman I would marry. I felt bad emailing Cathy and telling her I had met someone that I wanted to pursue a relationship with further. I let her know that I did enjoy spending time with her…but I still felt horrible: it felt like no matter what I said she would be convinced that I didn’t like her based on our first date. The truth was she just had really bad timing.

Things I Learned After Being Stood Up
I left the first date that had been scheduled with Cathy with a few thoughts on what I would do differently in the future:

1. Even if the restaurant is busy don’t get a seat until your date arrives when on a first date with online dating. Being stood up is awkward enough…adding the task of having to explain things to your waitress only makes things worse.

2. A follow up message or phone call for confirmation before the first date doesn’t hurt. Sending someone the text “So do you still want to meet me” is horrible. Instead, sending “Does 7PM still work for you?” or “I’m looking forward to our date tonight” are both good ways to get affirmation that they’re still coming.
3. If your date has expressed concerns with meeting people using online dating then make your first date as stress free for them as possible. Looking back, I believe Cathy found the idea of a short date where we took a walk and had a coffee together much more inviting than an hour of one-on-one time over a meal.
4. For all the good I found with online dating, the act of standing someone up seems to happen more often with it than with traditional dating. With online dating, it’s easy to drop off the face of the earth and never speak to them again. So even if you’ve not been stood up in the past, keep in mind it is more of a possibility with online dating.

Giving Someone a Second Chance
In my example, I ended up giving Cathy a second chance after she was a no-show. My action in this case is not an endorsement of giving anyone a second chance after they have stood you up. That’s really up to you. However, I do want to discuss some things to keep in mind if you are considering giving someone as second chance:

• Excuses are no good. The world we live in is all about communicating quickly and easily. If they had a spare 15 seconds then they have no excuse to stand you up. There are some very rare exceptions but I’ve never heard of a real-world example that I felt fit being an exception to the rule.

• Excuses will tend to be dramatic. I had a reader explain how a man told her he was in the hospital so she gave him a second chance. When he didn’t show up again for the next date, she was done with him (and rightfully so). He had the nerve to try to make a new dramatic excuse. Expect amazing excuses but be slow to believe them.
• If you are giving them another chance, YOU should set all the details of the next date. At this point, you are 100% in control and should set the date to whatever you’re comfortable with and to whatever works best for you. For example, pick a coffee shop close to your place or suggest they meet you somewhere when you are already planning to be out. They’re lucky to have a second chance at all and should be working within your schedule if they want to meet.
• Take your personal situation into account. It would be easy to say, “Never, ever talk again to anyone who stands you up!” I understand why this is most often a good answer but not always the best one. Were you attracted to them? Did you connect strongly over email? Did they express nervousness over online dating? Did they show remorse when you challenged them on why they would stand you up? The decision has to be yours in the end and details like these can help you decide.

All this having been said, in most cases if you have been stood up that should be the end of things. While I believe Cathy was nervous about meeting, if I’m honest a big part of the reason I decided to try again was because I had put so much effort into meeting her in the first place. Two months of communication to never meet was something I hated to consider. Were it not for that, it’s hard for me to imagine that I would have tried to meet her again. Perhaps not the greatest reason in the world…but we all have our own reasoning.

If You Are Thinking of Standing Someone Up…

If you are thinking of standing someone up…don’t! It’s a horrible thing to do to someone. You’re basically saying that you would rather give someone else an entire evening of discomfort instead of taking on the minute or two discomfort you would feel by calling them and canceling.

If you are uncomfortable with the date for some reason, just change the parameters of the date until you are comfortable. If that means changing dinner and a movie to 15 minutes over a cup of coffee, so be it. This is what I wish Cathy had done.

If you have decided you don’t want to meet them at all, instead of standing them up contact them beforehand. Let them know that you’ve decided you’re not comfortable with meeting and apologize that you are backing out. Text message, email, phone call….something! If you want to drop off the face of the earth at this point, fine. But don’t put them through a painful process when you have no intention of showing up.

I made it through dozens of dates before I was stood up so I don’t think this is an out-of-control problem with online dating. Still, it pays to be aware that this does happen.

Related posts:

1. Who Should Pay on the First Date?
2. Crass Men Hurt Everyone in Online Dating
3. My Online Dating Success Story

The Failure Phase

I started dating online in June many years ago. I had actually thought about signing up for an online dating service for months (maybe even a years if I’m honest) but couldn’t bring myself to do it. As I mention in my guide, I believe it took my loneliness to outweigh my pride before I started taking online dating seriously. The first time I signed up for a dating service was impulsive: I found a woman who seemed interesting and who seemed very accessible based on her profile and who also lived in my home town. So even when I finally did give online dating a chance, it wasn’t so much about planning as it was about making a decision on the spot.

My first dating profile photo…not particularly good

I was a little too satisfied with myself though and I had no idea how to move forward with the online dating process. Looking back, I can see that she was dropping hints that she wanted to meet but I was just too blind to how the process should have gone. At the time, I thought “Online dating is risky so most women will probably want to talk a month before we meet. If I ask her out too soon, she’ll never talk to me again.” If you have read my online dating advice, you know that I now believe this is an incorrect way of looking at online dating and I encourage my readers to meet other singles sooner rather than later. At any rate, I suspect she eventually became bored of waiting on me as she “disappeared” (that is, stopped responding to my emails). At the time I was very confused as to what went wrong.

For the next few months I basically had no success at all. I believe this failure was due to three issues with my approach:

1. First, my initial success contacting the first girl had me convinced things were going to be easy

2. Second, I was convinced that the most appropriate way to approach communicating with women was one woman at a time. I would email a woman, wait a few days and then if I didn’t get a response, contact another woman. This approach caused me to have very limited online dating opportunities.
3. Third, I still believed that women would want to talk for weeks or months before meeting.

If you look at the second and third bullet, these two approaches together create a very difficult dating environment to have success.

A First Date
Time passed and I found myself a few months into online dating with zero first dates and I felt horrible. However, in August of that year, I started to communicate with a girl who had a similar philosophy as me: talk to one person for a long time before meeting. With her, my approach actually worked, although it took over a month to meet. When we did go out, which you can read about here, it ended very poorly from my point of view. I found this depressing because I at that point I was approaching 4 months of dating online and only had one bad date to show for it.

After that point I went a few more months with basically no success. I was still going with the one-conversation-at-a-time approach so my opportunities were limited.

The False Success Phase

In the fall of that year, I had my first good date which ended up with us dating for several months. However, I was just making a new mistake in this case. We didn’t get along at all! We had totally different outlooks, we disagreed on some pretty core areas of our life and (for reasons still unclear to me) she went out of her way to keep our relationship a secret from her family. There were very few merits to the relationship and it was a horrible choice to continue dating her once I realized this.

However, at this point in my dating life I was more concerned with having success (however small) than I was with having a good relationship. I wanted to be able to say I was dating someone more than I wanted to have a good relationship. Over five months of failing with online dating had caused me to reach a point where I would accept any relationship, no matter how bad.

Fortunately, she broke up with me after a few months as she was moving away for a job. I was hurt by it at the time but looking back it was the best thing that could have happened (for both of us). Partly because it wasn’t a healthy relationship but also because it caused me to question my entire approach. I knew I was in a bad relationship even while it was going on but I fought to keep it going.

In some ways, this was same problem I was having with online dating in the first place: I was trying to make something work, no matter how many facts were presented to me that something needed to change.

I decided to reevaluate my entire approach to online dating and why I was dating in the first place. I committed to reading more dating advice both online and offline. Some of this advice was helpful but I found a large amount of the advice (especially much of what I found online) to be lacking. This experience with dating advice is what eventually led to the creation of this site, but that’s a story for another day.

The Success Phase

By January, I wanted to change how I was dating: I finally realized my failed approach was only going to continue to fail. I decided to approach my online dating life systematically and not just stick with what I thought was the best way to date online. I was going to be intentional about having success with online dating by trying the advice of others and also by simply experimented with how I was approaching writing emails or creating my profile or when having a first date. I didn’t have any “success” in January but I do consider this time period to be the turning point for my online dating life, from bad to good.

I started asking girls out more often and much more quickly. In the beginning (early in February) I wasn’t having much more success but I kept at it. I started trying to date just about anyone, if only to get more experience figuring out what worked and gaining comfort with all the first dates I knew I would be having.

It took a time but eventually I found myself with a date every other week, then I improved to one first date a week and at the end I found myself going on multiple first dates every week. The great thing at this point was I felt so great about all the dates I had planned I started asking women out in the “real” world. This is something I had never done before and I was even having some success there (lots of failures too though!) I had lost my fear with meeting women or first dates because I had so many opportunities a single failure meant nothing. Compare that to when I was attempting to talk to a single woman at a time where a failure meant everything. A single failure when talking to a single person meant starting from scratch. A single failure when talking to 5 women meant little more than that my schedule on Tuesday had just cleared up.

I met the woman who would become my wife in June, one day short of a full year of online dating. I knew right-away that we had something special and that night I contacted the other women I had scheduled dates with and canceled. I ended up calling 5 or 6 women, which was just another reminder of the turn-around in the success I was having. By the end, I had just as many first dates scheduled for the next two weeks as I had had in the first 9 months of dating online.

Looking Back

So what’s all this mean? Basically, it comes down to the fact that I dated online very actively for a full year and for 8 or 9 months of that time, it was a miserable process. The last 4 months were the exact opposite: interesting and exciting. I was really having fun. Even though I was thrilled to meet my wife and even though I immediately knew we were going to have something special, there was a part of me that was sad to see online dating go because I was finally doing it in a way that made the process of dating very enjoyable.

I wrote my guide with the hope that it would help others get to the “fun” part faster. That said, it is work. Even though I feel very comfortable with dating online now, I’m not going to kid myself and suggest that if I started dating online again tomorrow that I would immediately have tons of first dates right off the bat. It takes real work even when you know what you’re doing.

The biggest turning point was when I decided I would date women even though I strongly believed it wouldn’t lead anywhere. If you can change your goal from “I’m going to find and then date the perfect person” to “I’m going to date and then find the perfect person” you are going to have more success, in my opinion. I never plan on being single again but if I were I know I would follow this rule because it worked so well for me before. It didn’t just improve my online dating life, it improved my dating life. I found myself talking to women in the real world, asking them out even knowing it would likely go nowhere.

One other note: Kate, my wife, didn’t have a photo in her profile. My “old” approach of finding the perfect person and then dating her would have never allowed me to contact someone without a photo but my new approach did and it made all the difference.

Online dating is frequently frustrating and often can create a sense of hopelessness but I honestly had fun dating online the last 4 months. I stopped looking at women as a solution to my problem and started seeing them as people I could meet and have fun with. I stopped taking things so seriously and started giving everyone a chance (well…everyone within reason!)

Related posts:

1. Online Dating Guide: A Success Story
2. Online Dating Success Story: Post-Wedding Thoughts
3. Dating News: Breakup Tech Cleanse, A Bad First Date, and an Online Dating Success Story

To put it another way, if I go to the gym to lose weight, I would prefer that my trainer be someone who was at one time overweight. I want someone who understands both the struggle and the success. It’s far too easy for somebody with the metabolism of a hummingbird to tell people how easy it is to lose weight and that they’re just not trying hard enough.

photo by hart_curt

In the past, I’ve taken dating advice that tried to make my situation sound like a simple talking-point when it really wasn’t. I’m a very shy man. Any date I’ve ever been on has involved either me or someone who cares about me putting in some real effort. I struggled with rejection for many, many years and avoided putting myself in any type of situation where I might be rejected by a woman. I also took plenty of advice from plenty of people who thought my problems were oh-so-easy to fix (those people were wrong).

I overcame my fear of rejection but advice that says “just get over it” provided zero value in helping me accomplish that. In fact, this type of advice only made me feel depressed, as if something was wrong with me. Some of this advice almost drove me away from online dating entirely. I was convinced that I was failing when in retrospect the advice was just bad, at least for my situation.

What I’ve found with my own experience and while searching for valuable content for my readers is that so much of the advice out there is given in such a way that it has the possibility to hurt peoples chances as much as it helps. If I offer advice that convinces a single person that something is wrong with them causing them to stop dating, I’ve had the opposite affect I should be having. With that in mind, in my next article in this series I’d like to offer some of my thoughts on taking advice and recognizing the good from the bad.

Read Part 2: 10 Tips on Taking Dating Advice

Related posts:

1. 10 Tips on Taking Dating Advice
2. Should I Lose Weight Before Dating Online?
3. Online Dating Advice for the Shy

She did try it and for a time, things didn’t go very well. She met quite a few jerks and sometimes it seemed to me she was only dealing with men who knew how to treat her poorly. At this point, part of me felt horrible. I had felt like I had put her in a situation where she was hurt and lonely instead of just lonely. She persisted, moving from a main stream dating site to one of the niche dating sites (something like ChristianCafe although I honestly don’t know which service it was). Here, she had success.

A few weeks ago, I was able to attend her wedding to a great guy she met thanks to the niche online dating site. I really don’t think she could have hoped to find someone who would care for her more and the wedding was beautiful (even though we were stuck in a semi-blizzard).

Photo by Captivating Imagery

I think sometimes people think because online dating isn’t easy, that it’s impossible. Nothing could be further from the truth. Online dating does take commitment. Just because you’re staring at pages and pages of single people doesn’t mean you’re going to be in a strong, successful relationship in a month’s time. If you approach online dating with this expectation, then yeah, I can see why you might think no one would ever have success with online dating. If everyone approached online dating like this, the only people who would have success would be the very lucky.

Related posts:

1. My Online Dating Success Story
2. Thoughts on Online Dating Success Rates
3. Online Dating Guide: A Success Story

When I was single, I always felt like meeting women was very difficult. And for me, for quite a long time, it was. But then, almost over night things seemed to come together and I was meeting lots of women and I was even getting plenty of dates. Some weeks I would have multiple first dates and there were even a few weeks where I had more nights with dates than without. There were several things I changed over the course of about six months of trial and error that I’ll describe here.

First, when people discuss how to meet women I think there are two questions actually being asked:
1. Where do I meet women?
2. How should I act socially when meeting women?

I’m going to break down each of the questions based entirely off of my personal experience. Some of this advice may seem obvious but as a shy guy I had to learn most of this the hard way, by making lots of mistakes. I’m sure there are many other ways to meet women. For example, being born very handsome and charismatic is a great way to meet women (or so I’ve heard). Lots of money is said to do wonders as well. Sadly, I’ve no experience in either of those areas so I’ll stick with what I know!

Part 1: Where are the good places to meet women?

Online Dating…it worked for me…

First off (and you should have seen this coming), online dating is a great place to meet women. I’ve always been a shy person and one of my biggest struggles was always feeling uncomfortable approaching strangers. I found comfort in online dating as I knew everyone there was truly interested in dating, even if they weren’t always interested dating in me. If you’ve never tried online dating I’d highly recommend it. This topic is too broad to cover in detail here but I do cover the entire process in my online dating guide. I ended up meeting my wife through an online dating service so I’m a big fan.

Meet-up Groups

Co-ed meet-up groups are a great place to meet women. Meetup.com is a site devoted to helping people meet up (surprise!) and while it’s not advertised as such, many people using this service are using it to meet people from the opposite sex. I personally know two friends who have found dates through this service at events including a co-ed dodgeball group and hiking group. Additionally, another friend actually stopped going to his “beer sampling” Meetup group because it was turning into a “singles beer sampling” after a few weeks. These groups are great because there’s no pressure that you have meet someone but it is the hidden goal of many of its participants.

Places of Worship

If you attend a church or temple or synogogue , I would recommend temporarily trying another, preferably one that has a strong singles group if it’s an option. If you dislike the idea of changing your place of worship, you could try to find one with different schedule such as Saturday nights or a group that meets on weeknights. There’s nothing wrong with asking someone out at your normal place of worship but there are a few things that make this difficult. Primarily, there could be some discomfort if you ask someone out but she’s not interested.

Other Places I’ve Had Success

I had a lot of good luck at weddings. Unfortunately, that isn’t something you can just add to your schedule at any given moment. I’ve never had luck at bars…well, once but for the most part it was no good for me. However, I have had repeated success at house parties. The smaller atmosphere plus the fact that a quick word to the host can get you an introduction goes a long way.

Places I’ve Had No Success

I’ve been told that the following are great places to meet women: grocery stores, the gym, bookstores, sporting events and other similar places. I never had any luck at any places like this but they’re on most of the lists out there so I guess they’re working for somebody.

Image by pedrosimoes7

Part 2: How should I act socially when meeting women?

Comfort

First and foremost, I think you need to be comfortable when you’re meeting women. Note I say comfortable, not confident. Much of the advice out there disagrees with me on this, going for confidence over all else. However, I would have never labeled myself as confident and yet I had so much success. As with much of what I discuss here, tips for gaining appropriate comfort are covered in detail in my dating guide.

Accepting Rejection

You will have to learn to accept rejection. Aside from not being very out-going, I think this was my biggest hurdle with dating. I think that’s why online dating helped me so much. The rejection there is much more abstract but over time when you get turned down enough you realize it’s not so bad. Once I reached that point it was actually not that bad being rejected in person. It was never enjoyable but it did become acceptable.

Listening Works

I know many readers are probably looking for some formula for quick sex so this point is going to baffle you. I think you genuinely need to try to learn about her when you first meet. I suspect I’ve just lost half my readers with that one but I stand by it. First of all, when you try to learn about her it makes the conversations so much easier, particularly when just meeting. You not sitting there repeatedly thinking: “What do I say next? What do I say next?” or “How can I impress her? How can I impress her?” Instead you’re thinking, who is this woman I’m talking to? In my experience, she’ll notice. I’m not handsome or rich or strong or out-going or confident but if I could get to the point where I was having a conversation with a woman and I actually tried to learn about her, my success was through the roof. Remember: these women are people, not just conquests. Many times they can see what you’re trying to pull before you’re even sure of what you’re trying to pull. If she figures you out but that means she realizes you’re actually interested, that’s a good thing! Honestly, just give this a try for 10 minutes the next time you meet someone and see how it goes.

Attitude Matters

You need to make yourself available. You need to be friendly and positive. Again, this area was a struggle for me in the beginning. I didn’t realize it at the time but I often came off as distant or even slightly angry. Two things turned this around for me: being willing to smile a lot and actively trying to make eye contact. Again, as a shy guy I suspect I’m telling many people out there something that comes naturally to most of us. Still, keep in mind that you are making first impressions even when you don’t realize it.

Related posts:

1. Service for Dating Younger Men (or Older Women)
2. 11/03 Dating News: Social Dating, When to Meet, and the 6th Sense
3. Group Dating: Another Way To Date Online