Ask Hal

Page 5 of 6« First...23456

Meet My New Girl Friend

Meet My New Girl Friend

Dear Hal, I live in a relatively small community of about 20,000. We have a main street and a fair-sized big-box shopping center at the edge of town. For over 2 years, I had a very close relationship with a nice mature widow (as am I) here in town. For a variety of reasons, we

I Am Too Flirtatious. What Are The Boundaries?

I Am Too Flirtatious. What Are The Boundaries?

Dear Hal, I am a “young” 76-year-old who has been single for just over 4 years now following my wife’s passing. I am fortunate to have many friends who often host parties in addition to the get-togethers that are organized by our building complex. I attend almost all of these events and I enjoy “flirting”

Should I Tell The “Kittens” To Back Off?

Should I Tell The “Kittens” To Back Off?

Dear Hal, I am fortunate to see several ladies on social occasions and I enjoy their company for many individual reasons. One of my “dates” is a woman who I really like, but she dresses in a way that I think is a bit too provocative for some people (not me, however!). When I am

Pay Our Own Household Expenses

Pay Our Own Household Expenses

Dear Hal, I have been living with a woman for just over two years now, mostly in my home, although she has a place of her own in a different state where we have spent the past two winters. We pay our own household expenses. This winter, I asked her to upgrade her cable television

My Moustache Tickles Her

My Moustache Tickles Her

Dear Hal, My lady friend has told me that my moustache tickles her and that I should shave it off. I have had my “stash” for over 20 years and my kids say I should keep it. I really like this woman and I don’t want to lose her over something like this. What should

Pictures Of My Deceased Wife

Pictures Of My Deceased Wife

Dear Hal, Should I remove pictures of my deceased wife? I feel like it might be holding me back both dating-wise and emotionally. It has been three years since she passed away. Literally “hung-up” in New Jersey Dear Hung-Up, First of all, how do you feel about it? Do the images still bring you a

Separate Vacations

Separate Vacations

Dear Hal, I have a simple question for you. My lady friend and I have been living together for almost a year and we get along great. But recently the question has come up about taking separate vacations. Is that going to be bad for our relationship? On the go in Georgia Dear On the

Can I Drink Tonight?

Can I Drink Tonight?

Dear Hal My girlfriend drinks too much. She’s not an alcoholic, but on more than one occasion she will have 3 or 4 glasses of wine or an extra Martini and then she gets…well, sloppy. It is embarrassing. After I mentioned this to her, we will go for a period where she asks, “Can I

‘Tis the Season . . . to Shop

‘Tis the Season . . . to Shop

Dear Hal- With the holidays approaching, I am wondering what you suggest for gifts to the women in my life? I have several wonderful women who I see for dinners, movies, etc. but nothing more. I would like to get them something heartfelt, but not necessarily something that says more than it should. I am

To Gift or Not to Gift?

To Gift or Not to Gift?

Dear Hal- After three years since I got divorced (I am 66), I am seeing a really terrific woman (she is my age, divorced for seven years). We have been out together three times thus far and she is very affectionate and I know we are heading towards the bedroom very soon. Do you think

Page 5 of 6« First...23456