Clare: Clare weighs in on dates (the relationship kind)

Welcome to Ask Clare, our advice column.  Have a question, dilemma, or quandary?  Sent it to Clare in an email or on her Facebook page

Clare,

I’ve been dating a girl, let’s call her ‘Kim’ for a month or so. We’re in our forties and we’re both divorced with children. The other night we took our kids to The River to see a movie. Afterwards, we went to Pieology. Kim ordered first and got almost every topping they had. My daughter proceeded to ask for a pepperoni pizza. Kim suggested that my daughter get more toppings because they are free. It totally rubbed me the wrong way. More isn’t always better and you shouldn’t take things just because they are free. Is this a red flag that Kim has some issues? I don’t need to spend more time dating my future ex-wife.  -Over the toppings

Over the toppings,

There is a beautiful land where normal people live between one topping and all of the toppings. That’s where your ideal partner is. It would be one thing if Kim wanted all of the toppings just to enjoy them. It is a troubling sign that: A) she wanted all of the toppings because they are free, and B) that she tried to goad your daughter into her behavior. I say toss her out and start from scratch.

Clare

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Clare,

My boyfriend and I are incredibly happy but recently he’s been acting jealous and it is driving me nuts. I used to go out to bars a lot when I turned 21. Recently, after dinner my boyfriend wanted to go to one of my old favorites. Of course, we ran into a guy who I hooked up with in the past. When we were all talking, he wasn’t so subtle about it. Now my boyfriend seems extra interested in who I am texting and where I am going. I am sick of feeling like he is watching my every move. How can I get him to back off? – Red Barn Girl

Red Barn Girl,

Ouch! That’s one of the best reasons to avoid old hangs. Your boyfriend should not be jealous over what you did before the two of you were together. Sit him down. Tell him this guy and others are in your past – your boyfriend will be too if he keeps this up. You may want to think twice about returning to Red Barn to find his replacement.

Clare

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Clare,

When my girlfriend and I go out, she always offers to pay the tip since I pick up the bill. I make more and I think this works just fine…except she doesn’t ever leave enough. We go to dinner at a reasonably nice restaurant and she will leave a five-dollar bill on the table. She doesn’t see the bill but I am sure she reads the prices on the menu. Should I just tell her I’ve got the tip from now on? – Just the tip

Just the tip,

I see what you did there…I think you can handle the bill and let her know how much you need for an appropriate tip. It may feel awkward the first time since this isn’t what you two have done in the past but she shouldn’t give you trouble – especially since you’re paying the lion’s share. Knowing how to tip well is an important life skill that you want your future Mrs. to have. If you don’t know much about your girl’s finances, you may want to let her pick restaurants for the next few dates since she may not be able to afford tips at the spots you’re treating her to.

Clare

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