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Your Biggest Dating Crises—Solved


The authors of Worst-Case Scenario Survival Handbook: Dating and Sex on how to deal with rebounds, ticking biological clocks, and more.

By Josh Piven and Jennifer Worick


Q: I broke up with my ex a month ago and have since met someone I could swear is The One. Is this a rebound—or could it be the real thing?

Josh: I looked it up, and the dictionary has no firm definition of what constitutes a “rebound” when it comes to dating. It could be the real thing, and it could be a real bad thing; there’s no rule that says you can’t meet your soul mate the day after you’re dumped. I can tell you from personal experience, however,
There’s no rule that says you can’t meet your soul mate the day after you’re dumped.
that it’s best to take it slow when coming out of a relationship. You’re still emotionally vulnerable, and what seems like love may turn out to be lust. Sure, by all means date this new person. Just don’t start talking wedding (see above) until you get to know each other better.

Jen: I’ve actually written the book on rebounding (seriously, it’s called Rebound Rituals) and my main rule of thumb is to do whatever is going to ease your pain. In this case, you are demonstrating self-awareness: You realize that you could be rebounding and not thinking clearly. You could be relieved that you’re out of a devastating situation and surprised that good people and good relationships exist. Or your new date could be the love of your life…or the lay of your life. Whatever the case, enjoy it. Life is short. Whether it’s a rebound or not, live it, own it. Just don’t get married in the immediate future. Give the relationship time to find its legs and give yourself time to get back on your feet.

Q: I met a woman I really like, but she’s very vocal about her interest in marriage and kids and it’s freaking me out. Can I tell her to just put that on hold till we’ve gotten to know each other?

Josh: It’s entirely appropriate for you to tell her, straight up, that you are not yet ready to get married, to her or anybody else. But guess what? The cat’s out of the bag: This woman is looking for a life partner, whether she says it plainly or not, and her actions are probably going to be toward this end (china and wallpaper patterns, anyone?). You need to make it very clear that family life is not happening any time soon for you, and she needs to be comfortable with that—or find someone else.

Jen: Wearing a biological clock on your sleeve isn’t the proper accessory for early dates. While it’s nice to know that she has an agenda up front, it can get in the way of actually getting to know someone. And she’s probably shooting herself in the foot with this approach. Perhaps she’s so busy trying to size you up for a particular role that she’s not trying to get to know you. So yes, be honest with her: Tell her that you appreciate that she’s goal-oriented. However, you want to enjoy the process of dating, and you can’t do that with her agenda uppermost in both your minds. With any luck, she won’t cross you off the list and move on. Maybe she’ll actually chill out and connect with you.

Q: He wants me to meet his parents after three dates; is it too soon?

Josh: That depends. Yes, if he wants to fly you across the country to meet them. But if you’ve had three great dates with some intimacy, then I’d say it’s not too soon, provided they live close by—which means he’s not making a major commitment of time and money to introduce you. I’ve always felt it’s illuminating to meet the date’s folks, since it gives you a new perspective on their upbringing. And consider it a good sign that he’s not estranged. Of course, there’s always a
If you say “no” to meeting the parents, it may indicate to him that you’re not serious about the relationship.
chance you may not like what you find (think Meet The Parents).

Jen: In my “professional” opinion, meeting the parents should happen a few months, not a few dates, into a relationship. But there are always exceptions to this rule, and this is a loaded situation either way. If you say “no,” it may indicate to him that you’re not serious about the relationship. And on the bright side, as Josh mentions, you have a chance to glean a lot of information about him from the get-go by observing family dynamics. A friend of mine met fifty of her new date’s relatives after only a few dates. It was a big holiday gathering, she had a great time, and, best of all, they are still dating.

Q: Since we've gotten serious my date has been gaining weight at a rapid pace. Can I say something?

Josh: Yes, but “skip a meal” is not what I’d suggest—it’s critical to be tactful when confronting such charged issues. It’s quite possible there is an underlying cause of the weight gain completely unrelated to you or your relationship (work stress, family problems), so keep this in mind, and be sensitive to your partner’s feelings. I suggest bringing it up using some variation of the following: “I’ve noticed you seem to be putting on weight, is everything OK? Are you feeling alright?” I know that sounds harsh, but my gut feeling (excuse the pun) is that you’ll get better results by addressing the problem head-on than by trying “subtle” hints like preparing dinners of steamed broccoli and signing your date up to train for a marathon.

Jen: Of course you can say something—but you may not like the response you get. Turn the mirror on yourself before opening your mouth: What do you look like? Are you fit? If you feel as if you’re in good shape, then I agree with Josh that you can broach the subject…delicately. We all want to feel safe in relationships and if you’ve gotten serious, you need to foster a supportive and caring environment for your significant other. “What’s with the Shamu weight gain?” isn’t exactly the most loving approach. Ask your date some questions to find out if the weight gain might indicate a bigger problem (deep funk, stress, new medication, inactive lifestyle). Say that you’re worried about his or her health. Encourage your sweetie to get off the couch by creating rituals: Take a walk every night, or take up a sport together But if you are a health fanatic and your darling is not, you may just have to live with it; this person’s your lover, not your training partner.

Q: He wants us to go on vacation together after just four dates. Should I go?

Josh: I guess the answer depends on whether those dates included breakfast the next morning. Seriously though, the nature of your previous dates should play a role in your decision. If you’ve had a few coffees and some lunches—and no heavy petting—then it seems a bit too soon for a vacation (especially since you’ll probably be “double occupancy”). If, on the other hand, you’ve been intimate and things are going really well, then a short vacation seems OK to me. If it were me, I’d avoid a long trip (more than a few days), and I’d make sure it’s someplace you can get home from quickly and with minimal inconvenience if things go south.

Jen: Vacations often make or break a couple, even if you’ve been dating for years. All issues, both minute and major, rise to the surface. You might want to try spending the weekend together first before taking your show on the road. Forty-eight hours of togetherness in your hometown or apartment might be a good litmus test of whether the two of you can leave on vacation and both return alive. On the flip side, if you’re curious about how compatible your date is for a long-term partner, go for it and book that island getaway. After one week of enforced closeness, you’ll have a pretty good idea if the relationship can go the distance, or if after three days, you can’t stand her annoying habit of picking her cuticles or his penchant for planning every minute of your day.


Josh Piven and Jennifer Worick are co-authors of The Worst-Case Scenario Survival Handbook: Dating & Sex; www.worstcasescenarios.com.

*This column is for entertainment purposes only. It does not contain professional advice. The authors are not liable for any use or misuse of the information it contains.


Do you have a difficult dating situation you need help with? Share it, and advice on your dilemma could appear in a future issue of Happen.

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