When you’re on a second date and it’s going well, then you become more and more apt to share personal stories. If you feel comfortable letting your guard down and opening up, that’s great! Here are a few tips to help you get there:

• Make sure the other person is also sharing, and therefore is on the same page in regards to the date going well and wanting to get to know you better and allowing you to get to know them — sharing should not be one-sided
• Keep the topics positive, talk about things that make you happy
• Don’t start the “ex” or divorce/widow conversation just yet
• Stay away from relaying stories of your dating past — as funny as some of our 100hookup stories are, this is not the time to exchange them

Be a good listener; don’t interrupt and make sure to ask a few questions to show you’re giving your date your undivided attention. Bonus points for being an observant storyteller — don’t drone on and on without noticing if your audience has lost interest. You’re look for a connection; the more you share and find commonalities, the closer you will feel.

Follow Me!
Instagram
Facebook
Twitter

I had really underestimated my enemy. So after I was severely injured and thrown into that pit somewhere in the Middle East, I knew there was no way out. However, with the help of the creepy old clairvoyant man with the glass eye, that other guy, and a lot of push-ups, I learned that I could climb my way out if I wanted it badly enough. I eventually got out of that pit and saved the world and had sex with women and stuff.

However, if that scenario had ever happened to me, I would have writhed on the ground with my broken back until I eventually starved to death. Plus I have no health insurance. Those Afghani pit-prison doctors are real penny pinchers. If they hang me from a rope and kick me in the back, which apparently instantaneously cures broken spinal cords, my deductible will be through the roof, which I apparently will not be, because I will still be stuck underground.

I really need to make sure that I incur no serious injuries without health insurance. If I do, I need to make damn sure there are no giant pits in the ground that super villains, aware of my lack of health insurance, could throw me into. I actually do have health insurance, ladies. I needed to say that I didn’t for that joke. I realize that almost nobody will understand the reference, and if they do, they will still not laugh because it is not funny.

I’m not good at bouncing back from setbacks. When my camera got stolen like five years ago, I freaked out and eventually deteriorated in my bed for three weeks until I couldn’t move from hunger, and couldn’t eat because I couldn’t move. When I wrecked my car four years ago, I couldn’t bring myself to start the process of buying a new car until it got to the point where I tried to walk to the grocery store on a hot day, and collapsed because I was still malnourished from being underfed due to the camera incident a year earlier.

I’m making  a slow improvement in my ability to hold my own when I’m with women. About a week ago I graduated from many first dates to my first second date in a very long time. Although the third date was called off, and I’m still recovering from that, I think that that was a good confidence builder. Starting tomorrow, I’m going to exclusively wear tuxedos, a top hat, and a pocket watch, and walk around telling women to fetch me things. This is an upward linear trajectory, and I do not see how it can fail.

You know you read the title of this post and knew exactly how I felt. We’ve all been in this situation. You go out on a mediocre date, thinking that since your date wasn’t any better off than you were, that she will probably want to go out again. But she doesn’t. She doesn’t reply to your text that followed the Three Days Rule. Or your follow-up phone call. Or notice you when you made your nightly rounds around her house.

But seriously, she never responds to your text, and you become upset. Then you wonder why you became upset in the first place. You never really liked her. You just like being liked. If she had responded positively to your text, you probably wouldn’t have gone out with her again, anyway. You are just the worst. Not good enough to warrant a second date and not nice enough to allow one. You have two options. Either up your game to the point where girls fall for you all the time, or drop your game to the point where you’re willing to go out again with anybody. Either way, you will be going out with people, instead of stuck in a place where you go out with nobody, which is probably your bedroom. You don’t want to be stuck in some horrible limbo state where you can’t achieve either.

However, remember, in the words of Mitch Weaver, “No matter how bad life gets, there is always beer.”

My friend Julie recently a met a guy I’ll call “Darren” on 100hookup. It turns out they have a mutual friend who endorsed the match and the two were on their merry way to a first date. They met for drinks and Julie says it was a great time — there was constant and natural conversation, there were plenty of commonalities and there was mutual interest in seeing each other again.

Darren texted Julie the following Thursday morning and then called and asked her to go to dinner and a play on Saturday night — Prime Date Night! Julie was excited, needless to say.

Saturday night Darren picked up and then asked her where she wanted to eat. She was taken aback by the fact that he didn’t have any plans in mind, but she quickly rebounded and suggested a new place nearby. Dinner conversation didn’t flow quite as well as it did the week before and when the bill came Julie made a move towards her wallet, offered her credit card and Darren accepted. And as they were leaving the restaurant, entering and exiting the theatre, Darren not only failed to hold the door open for Julie, but let it fall shut behind him as he kept walking. The combination of all these faux pas was crushing as Julie was really excited about the prospect of Darren.

Julie was bummed but I convinced her to give Darren another chance if he were to ask her out again. A few days later she received a text from Darren saying that it was nice to meet her but they would be better off just as friends. Julie wasn’t so crushed because of the last date letdown, but still she was perplexed. I reminded her of the multiple faux pas he committed and pointed out that at least he was nice enough to not leave her hanging. We’ll never know what went wrong between date one and date two, nor why Darren wouldn’t give it one more shot, but he probably had a list with a few of his own grievances against Julie, faux pas that she committed unknowingly.

So how does something so promising fail so quickly and how can you keep these little disappointments from getting the best of you? Rollercoaster dating is unfortunately a normal part of dating and only hindsight will help you to see that the rollercoaster is actually weeding out the losers. And by losers I simply mean losing those that are not right for you. It’s better that the second date was such a doozy for both Julie and Darren because they didn’t waste any more time on something that ultimately wasn’t going to work out. Luckily, both of them saw the signs and neither was overly disappointed it didn’t work out. Maybe it’s realism, maybe it’s pessimism, but rather than getting your hopes up super high for each new date, try to just get your hopes up, say, medium high with a dash of sensibility.

Dear Tamar,

I recently accepted a Sunday brunch as a first date from a widower. He mentioned that a year had passed since he’s become a widower and he was seriously seeking a partner to share his life with. He also made remark about an upcoming dinner date where a woman was going to meet some of his friends. Aside from this awkward comment, the date was lovely and as we parted he suggested a second date.

Another weekend passed, phone calls and emails when finally a date was proposed by email but not for another two and a half weeks, again on a Sunday but this time for dinner. He seemed like a relatively normal guy, so accepting the date wouldn’t have been out of the question except clearly I’m not at all on this man’s dating radar with a month between dates selected on Sundays.

Should I just say I’m unavailable, not answer, or acknowledge that he find me if and when his dating schedule opens up? I certainly understand dating a number of people simultaneously as you attempt to find the one, I do likewise. But he’s asking me to make an hour long trip back and forth on a work night when I’m obviously not a priority. It seems incongruent.

Dear Inconsistently Interested,

I think you already know the answer to your question, otherwise you wouldn’t bother asking, right? It sounds like you just want reassurance that rejecting the date is the right thing to do. But, and this is a big BUT, it is possible that he was dating someone, it got serious but didn’t work out, and now he’s getting back in touch with you because he felt a connection. You could accept the date but go on it knowing not to expect much and hopefully be happily surprised. It sounds like this guy caught your fancy so if you’re still unsure just ask him what’s going on. He may be surprised by the question and you may not like the answer, but if it’s going to continue to bother you then why not ask? Good luck!

After learning many (two) important lessons from my apocalyptic-soul-crushing-equivalent-of-a-first date, I assured myself that, by definition, the next date could not be any worse.  This time I would not blindingly dive into a pit of uncertainty.  I had to arm myself.

First, I decided to read information posted about people before deciding to meet them in person.  Last time, my criteria for a date consisted of the other party being a girl.  This time, maybe, I would check to see if we had some, or any, shared interests. The first girl’s profile I looked at said that she liked food.  I like food, too!  Bingo!  Let’s look at more things!  We both like attending events!  This is unreal.  Her “About Me” section was pleasant and she seemed like a really nice person.

Second, I decided that I would chat online with someone before I rush and ask a stranger out to dinner.  I wasn’t yet aware of the feature where you could immediately chat with anyone else that is online at the same time.  I sent the same girl an email, which began a nice back-and-forth conversation.  Once I felt comfortable, I asked her to dinner.  She said yes!

We went to a quasi-fancy Italian restaurant, and it was quasi-expensive.  We both ordered spaghetti, and it was quasi-tasty.  The entire night had an awkward tinge to it.  I don’t think there’s any way to meet a person for the first time after talking online for so long and not feel a little uncomfortable.  If there is, maybe that is love.

Though there was never a second date, I left the first date feeling just fine.  The one date fulfilled all the social and food requirements I needed for the night.  Though I did want to see her again, she apparently did not.  Since I had nothing to lose, I asked her why she didn’t want to see me.  She responded by saying that though I was a nice guy, I mentioned bodily functions too much.  Who knew?

It doesn’t feel good when someone doesn’t respond to your email, accept your invitation to chat via Instant Messenger, or call you after a first or second date, however, these are inevitable parts of not only the online dating experience but also dating in general. Over time, and through experience, we all might get better at letting these disappointments roll off our backs; however it is human nature to feel a sense of rejection in each of these situations. This feeling is the price we pay for putting ourselves out there, and giving ourselves a chance to meet someone special.

The alternative to this proactive approach is that we sit back and wait for someone to find us and sweep us off our feet, but is that really a likely scenario? Even if a more passive, “wait and see” approach was a viable option, does that really guarantee that we aren’t going to incur any negative feelings from the dating process just because the other person found us and put themselves out there first? With the ball in our court we still stand the chance that our response won’t be perceived well, either via email or on a first date, and that will abruptly end the interaction.

Furthermore, waiting around for people to contact you limits the number of people you meet, and leaves you at the mercy of those who randomly stumble across your profile. This is in stark contrast to someone who puts themselves out there by continuously looking for people that attract their interest, and then attempting to begin a correspondence with them, who in the process might run more of a risk of getting hurt or disappointed. But they also have a much higher chance of meeting a lot of interesting people and having an abundance of new experiences in the process.

Maybe my more proactive approach to dating isn’t the norm.  I know that guys are the ones who are typically supposed to take the lead in these types of situations, but I say regardless of your age, sex or past dating experiences that we all owe it to ourselves to embrace dating as a fun and unique challenge where each experience is different and an opportunity to develop into something great. So please don’t sit back and wait for the perfect situation to fall into your lap when you can take control by going out and finding it for yourself. Sure, along the way there will be some disappointments and agonizing moments, but there will also be ones of pure joy and satisfaction, which in my opinion makes it all worthwhile many times over.