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Sex with Dr. Jess


July 25, 2018

Dating Questions Answered

The Morning Show viewers have dating questions and we’ve got answers. Jess joined Carolyn and Jeff this morning to weigh in on a few of their viewers’ dating dilemmas.

If we’ve been chatting a few weeks and he hasn’t asked to meet in person, is he really interested in a relationship?

He’s interested in chatting, but perhaps that’s it. You’ll never know unless you ask, so give a specific timeline with a request to meet. “Let’s set a time to meet in the next week.” If he’s not open to meeting in the next week or two (and he doesn’t have a good reason like he lives in Georgia), it’s unlikely he’s as interested in an in-person relationship as you are. This, of course, applies regardless of gender.

It’s not uncommon for people to chat on apps for weeks and even months prior to meeting and one study found that the longer you wait, the more likely the first date will be disappointing. But it’s also not uncommon for people to chat for months and never meet up. If you want a relationship and don’t have time to waste, speak up now and see how it goes. You have nothing to lose.

I’m 55 and widowed. My friends say I’m too picky and that’s why I haven’t found a partner, but I don’t want to lower my standards. Should I listen to them or just stay happily single (I live with my best friend and life is good)?

Don’t lower your standards. But don’t be inflexible either.

Many experts will advise you to avoid the big topics like kids, politics and financial goals during the early stages of dating so that you can get to know one another first, but at 55 I think you know what you want and if something is a deal breaker, you don’t need to spend time avoiding the topic.

My best advice: Focus on how a person makes you feel instead of assessing them for assets and deficits. You don’t want to compromise on the big stuff like values and whether or not you want to date someone with young kids, but it might be worth letting go of the superficial expectations like height and a shared interest in a specific hobby or sport.

I’ve been ghosted by 2 guys and now I’m afraid to date. How do I get the confidence to get back out there?

Ghosting has nothing to do with you and everything to do with their bad manners or their inability to express a desire or feeling that they believe will disappoint you.

You might feel shame, anger or embarrassment, which is natural when something that you thought was going well was interrupted, but underneath it, you’re likely hurt. So go ahead and hurt and tell someone you trust. Talking about negative feelings can change the way we feel and address some of the shame that breeds in secrecy.

If you’re nervous about dating, do so in more unconventional ways. Go on group dates with friends. For example, if you’re meeting friends at a ballgame, ask your date to come along. Greater attachment to your social circle may increase the likelihood that they’ll aim to treat you with greater respect (even if it means admitting that it’s not working out).

And don’t worry about closure in terms of looking to them for an explanation. If this person doesn’t have the confidence or manners to tell you “Hey – I don’t think this is going to work out”, you don’t need to worry about their opinion of you or assessment of the relationship in general. Instead, find closure by looking at the relationship realistically: was it as serious as you thought? Did you really want it to be something long-term? Did you really know them that well? Had you really connected intimately? In retrospect, you might find that the breakup was what you would have ultimately wanted even if the method was hurtful.