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When To Propose?


Reader’s Question

Hey Doc,I’ve read your book but may need coaching on a little conundrum. Sometimes when you get a puzzling result, you have to call in a specialist. I first laid eyes on Jill when she walked past me on a flight from Europe to New York. She made prolonged eye contact that suggested, “I’m interested and available.” I played it cool and bumped into her in baggage, which gave us plenty of time to talk and confirm the lack of a wedding band. I kept the conversation light, funny and interesting. I casually grabbed her phone number, waited a week to call and set up a lunch date. This led to a casual romance filled with “adventure” dates (hiking, parasailing, etc.) that started out as a once-every-two-weeks kind of thing and then progressed to talking on the phone every evening by the fifth month (I kept the calls no longer than 10 minutes to set up more dates). Here’s my problem. Through a professional connection, I got word that Jill’s ex-boyfriend, was pursuing her big time again, even though they’d broken up a year previous to my meeting her. Naturally, she’d shared a few details about him along the way, but I had no idea that this guy was rich. I’m talking majorly rich. I do well, but quite
frankly, I’m happy where I am, make a good living and plan to retire when I hit 50 to enjoy life instead of working till I drop. Here’s the rub: Apparently his biological clock is exploding or something, and Jill is mid-30s herself. She’s dropped lots of little hints about having babies with me — meaning she wants to get married ASAP. But I know that your MO is that you don’t even think about getting serious with a woman until you have a solid year of Flexible Giving under your belt with her, and I’ve only got six months. Jill also doesn’t seem overly materialistic, but in my experience you never really know with women. To her credit, Jill has made it pretty clear to me that this guy is coming on strong, sending flowers, love notes and asking to get back together. Jill has said that the reason they broke up to begin with was that he was a “workaholic” and unavailable.  Even so, I’m playing this cool and confident. I didn’t overreact at all upon this “news,” and kept up the Challenge and mystery (I still leave for weekends with the guys for fishing expeditions, although Jill tries to make “demands” on my time). I would guess that her Interest Level has always been at least in the 90s, but with Rich Boy putting himself back in the picture, I’m questioning that for the first time. Meanwhile, Jill is still dropping marriage hints and saying that she’s more or less ignoring her ex’s requests for dates and told him to stop contacting her. My question is this: Should I stick to the programme and wait another six
months to pop the question, or should I put this relationship into overdrive and head toward marriage more quickly? I don’t want to lose her over a perceived reluctance to walk down the aisle. Stew – who is curious to see how she’ll react to Rich Boy

Doc Love’s Response

Hi Stew, You make an excellent point about calling in a specialist when you face a dicey situation. Most men do not realise how deep my techniques and principles go when it comes to their problems with women. Guys send me
emails two pages long describing their difficulties with a woman, and they expect me to give them a one-sentence Band-Aid to solve everything. It doesn’t work that way. In reality, they need major surgery. Like my cousin Brother Love says, “If you got problems with women, there ain’t no quick fixes.”

Let’s move on to Jill. Her prolonged eye contact with you said she was interested, but it didn’t say that she was necessarily available. So you shouldn’t have jumped to any conclusions.

You should have been seeing Jill at least once a week instead of once every two weeks. And, remember, the telephone is used to get a date, and that’s all. I know you kept your calls short, Dewey, but it’s not how long the calls last; it’s the frequency of the calls that’s just as important. By calling Jill all the time, you’re killing Challenge, Dewey.

When you got the information about Jill and her ex from your professional contact, I hope you didn’t tell him that you were dating her. How do you know he wouldn’t take that information and run with it straight to Rich Boy? Still, you had to listen to what he told you, even if you weren’t sure of its truthfulness and accuracy. As I’ve told you guys before, you have to be a love detective and factor in all the evidence.

Dewey, you need two years of Flexible Giving with a woman before getting engaged — one-and-a-half years at the very earliest. One year is not long enough because at that point, you’re still going out with a stranger. Like my Uncle Jethro Love says, “After only one year with a woman, you ain’t seen all her warts yet.” It’s true as you say that you never really know with women, and I congratulate you on being aware of it.

My question to you is this: if Jill loves you so much, why is she talking to you about other men? I would advise you not to talk about your exes with her, so why is she not showing you the same class? Why can’t she prevent herself from baring her soul? To you Psych majors, women with Interest Levels in the 90s don’t talk about other guys.

The key to this situation, Stew, is what Jill tells her ex. If she orders him to stop contacting her — assuming she’s not lying to you – it’s great. But how truthful is she being with you?

No way you can pop the question now, pal. You have to wait another year and a half before even thinking about it, given the present circumstances with Rich Boy. So, no, you shouldn’t put this relationship into overdrive. You shouldn’t do anything until this other guy is completely out of the picture. I don’t like the fact that he’s still coming on to Jill. Here’s something to think about. When Jill gets an email from him, does she erase it or does she read it? When he mails her flowers, does she mail them back? When he sends her a love letter, does she write on it “THIS RECIPIENT IS DEAD” and return it? The point is this: How hard is she really trying to get rid of this guy? My suspicion is that she’s not trying all that hard since she keeps letting him contact her.

Your problem, Stew, is that you have an ex-boyfriend lurking in the background, which is a big no-no. Until that situation is completely cleaned up and you get at least two years in with Jill, don’t even think about marrying her.

Remember, guys: If she’s talking to an ex, you have to smell a rat.

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