Going on 100hookups can be fun and entertaining (or dull and torturous, but this column is dedicated to the former!), so how do you turn a 100hookup into something more?

After the first date, a man who is interested should call the woman within two days, if not the next day. You can even send a text later that night or the next morning saying how good of a time you had – but don’t get in the habit of texting at this stage! (My anti-texting rampage is yet to come.)

When you call after the first date, make immediate plans for a second date, preferably within the next week. You don’t want to lose momentum. You’re getting to know each other, enjoying each other’s company and building on the chemistry. If you know you have a business trip, try to squeeze another date in before you leave or make plans in advance for when you return. Whomever is out of town should try to call once or twice while away but otherwise, you shouldn’t be spending too much time on the phone at this point, just let the other person know you are definitely interested and not blowing him or her off.

When you plan the second, third and fourth dates they should continue to be casual, comfortable and full of quality-time. That means no friends, not too much alcohol and no weddings of your third-cousin-twice-removed. Get to know each other sober and alone before introducing each other to your crazy fraternity brother or even crazier Great Aunt. Daytime dates are also a good option. Go for a walk in a park with a picnic basket to eat while you watch the sunset. Go to the zoo, the fair or an amusement park, or even miniature golfing or go-cart racing. Find a fun activity that will allow your inner child to come out, where you can laugh, and engage in some physical contact that’s not overtly sexual.

Dear Tamar,

I just started dating this girl that got out of a 9 year relationship a few months ago. We’ve been texting all day, talking all night, have gone out 4 times in 2 weeks and things have proceeded pretty quickly. She seemed to really like me a lot but then after our last date she sent a text saying kissing another person was new to her and she needed to get used to it, but really enjoyed it. After that she cancelled our plans and hasn’t returned my calls. Is this common for someone getting out of a long term relationship? Should I give her some space or try harder? What’s the best advice you have of getting her back into the groove of how we were until she freaked out? Thanks for taking the time to read this.

Dear Rebound Relationship,

It sounds like your girl is, as you said, freaking out. She hasn’t been single in a very long time and moved a little too fast with you because she’s forgotten how to date. She may also be feeling lonely because she hasn’t actually been alone in a very long time. Less than 3 months recovery time after 9 years isn’t nearly enough time to really get over such a long relationship and it’s normal for her to back off after getting too close too soon. Chances are, she’s far from ready to enter a new relationship. I suggest taking a proactive role: send her an email letting her know that you understand she needs her time and space and that you’ll be there when she’s ready. This could and should take a minimum of a few more months. In the meantime, you need to start dating other people and if you’re still available when she’s ready, then great! Sorry if this isn’t the answer you were hoping for, but if you force the situation with her right now you will only scare her away. Good luck!

Dear Tamar,

I’ve been seeing a man who’s not hookup that I met on a dating site 7 months ago.  We’ve said we love each other, however when we first met, it was Hanukkah and he bought me a huge number of gifts and it felt uncomfortable and overwhelming.  He also bought a menorah and a book about Judaism. It felt like too much for me and he felt rejected by the way I felt. Since then, I thought we had moved on and have spent almost every day together. Recently, he was reading my e-mail and saw a letter I had written to my Rabbi back in January where I had doubts about the relationship because of the fact he wasn’t hookup. He broke my trust and has apologized but feels hurt I felt that way when we had already been dating for a few months and wants to take a break for a month. I want to respect his wishes but I miss him and know he misses me as he did write me yesterday. I’m just trying to understand whether we have broken up or not and if I should move on or if we are truly taking time to figure out what we want with the intention of possibly getting back together. I don’t understand how you can work something out without talking about it. Can you provide some input and help me to understand? Thank you!

Dear Dazed & Confused,

My initial impulse is to ask: why are you on 100hookup asking for advice about a relationship with a non-Jew? But the answer doesn’t matter, I’m happy to help as long as you answer a question for yourself first: how important is it to you to marry a Jew? This answer does matter. When you first had doubts, you went to your Rabbi. Now you have doubts again and you’re coming to 100hookup, so my inclination is to believe that religion is important to you and while you’re on this break you should really think deeply about it. It sounds like this guy might be willing to convert, have you discussed it? If you want to be with this guy – hookup or not – you need to get him on the phone and then in person to talk. A few days apart to think things through is understandable, each of you needs to put things in perspective and decide what you want from each other, if anything. But now it’s time to get talking because you’re right – you can’t work on a relationship without both parties being present. Good luck!

How does the past mark the future of how we behave now while dating? For me I know it has had an important impact.  I’ve compared and contrasted while in the process of getting to know someone. How can you or I change this?  We all do it, and unless we can begin something new with a clean slate we will never attain what we are searching for.

Firstly, it is time to let go. Learn from the past relationships. Decide what was good and what was not so good.  Take those lessons with you, but put those people away and close the door.

Secondly, be prepared for the new people to remind you of that last person and/or relationship. Don’t be surprised. We tend to repeat patterns and if they are positive healthy patterns let the process work. If the new person is pushing the same buttons and triggering negative emotions move on and move forward.

Thirdly, remember dating is practice. It teaches us what we want and don’t want. Nothing is ever perfect and if we hold onto the past the future will never come. Remember, stop and pay attention. Let go and enjoy yourself.